House of Siesta: our home by the coast. We’re opening our doors not to a regular rental but to our own home, created with love so guests can feel truly at home too. Just 0.7 miles from the #1 beach in the USA and minutes from Siesta Village, it’s spacious, welcoming, and perfect for two families to share. Enjoy open living, a cozy patio with grill, plus beach gear, bikes, toys, and games. A place to reboot, reconnect, and make unforgettable memories. The space 🛏 Bedrooms & Bathrooms -Master Suite: Queen bed + private full bathroom -Second Bedroom: Queen bed -Kids’ Room: Two bunk beds (sleeps 5) -Hallway Bathroom: Full bath with tub -Laundry Room: Washer & dryer for your convenience 🍴 Living Spaces -Open-concept living & dining area -Fully equipped kitchen -Bright, airy design with coastal touches -Smart TV - Island seating - Separate dining table 🌞 Outdoor Amenities -Private patio with dining set & grill -Lounge chairs & umbrella -Lawn space for kids to play -Bikes included for exploring the island 🏖 Beach & Family Gear -Beach chairs, toys, wagon & tent -Games for family nights -Fishing essentials for anglers -2 bicycles ready for adventure 🌆 Location Highlights -Just 0.7 miles from Siesta Key Beach 🌊 -Minutes to Siesta Village with delicious restaurants, shops & ice cream spots 🍦 -Easy access to fishing, boating, and all of Sarasota’s attractions Guest access Every guest is given a private, individual code to access the home via the Yale lock.

Charming 3BDR home 0.7mi from the #1 beach

🦩Exclusive Amenities Include: • Private Heated Pool & Hot Tub • Water Front Home, Canal Access • 10 Minute Walk To Siesta Key Beach & Less than 1.5 miles from Siesta Key Village • 3 Bedrooms, 2 Bathrooms (Sleeps 9) with Linens Provided • Screened-In Outdoor Patio • Outdoor Putting Green • Outdoor Gourmet Kitchen & Bar • Fire Pit & Gas Grill • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided The space 🌴 Gulf Birdie | Waterfront Pool, Hot Tub & Putting Green, 0.5 Miles to Siesta Beach  💖 Why You’ll Love This Home Canal waters shimmer in the backyard as palm fronds sway overhead. A breeze flows while you grill in the gourmet outdoor kitchen. Lounge in the private heated pool or spa, challenge friends on the putting green, and enjoy a fire pit under a starry Florida sky - all just 0.5 miles from Siesta Key’s white sand beach. Inside, soft coastal tones and textures create a serene space to unwind in style.  👨‍👩‍👧 Perfect For Families, couples, or multi-generational groups seeking a luxurious, beachy escape with walkable Gulf access.  🎞️ Imagine This Start your morning with coffee on the screened lanai as the canal glistens in the sun. Slip into the pool for a refreshing swim, then stroll 0.5 miles to Siesta Beach for soft white sands and turquoise waters. Back home, grill lunch in your private outdoor kitchen while the kids practice putts on the green or paddle along the canal. As the sun sets, soak in the spa and gather around the fire pit with cocktails. Inside, comfortable coastal décor and thoughtful touches invite you to relax after a day of fun and sun.  🛌 Where You’ll Sleep • Bedroom 1: King Bed, Ensuite Bath, TV, Private Balcony • Bedroom 2: Queen Bed + Twin Bed, Shared Hallway Bath, TV • Bedroom 3: Two Twin Beds, Shared Hallway Bath, TV • Bonus Room: Queen Sleeper Sofa, Main Living Area  📍 Explore the Area • Waterfront Setting – Paddle the Canal or Soak in the Views from Your Own Backyard • 0.5 Miles to Siesta Key Beach – Walk or Bike to One of the Country’s Top-Rated Beaches • 1.5 Miles to Siesta Key Village – Island Dining, Boutiques, Ice Cream Shops, and Coastal Nightlife  ⌛ Don’t Wait - This waterfront gem books quickly. Your reservation includes peace of mind with our CottageClean program, featuring a 6-hour deep clean and 35-point inspection.  🔎 Need to Know: The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. The primary guest making the reservation must be at least 26 years of age.

Gulf Birdie | Luxury Waterfront Home with Pool

Exclusive Amenities Include: • Screened-In Private Heated Pool • 4 Minute Drive To Siesta Key Beach • Less than 2 miles from Siesta Key Village • 3 Bedrooms, 2 Bathrooms • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided • Beach Towels, Chairs, Cooler, & Caddy Provided • 2 Bikes • Gas Grill • Dog-Friendly with a Fee (1 dog up to 25lbs) The space 🌴 Casa Del Mar | Private Heated Pool, Short Drive to Siesta Key Beach  💖 Why You ll Love This Home Casa Del Mar offers a comfortable and well-located Siesta Key retreat designed for easy beach days and relaxed time at home. Just a short drive to Siesta Key Beach and under two miles to Siesta Key Village, this three-bedroom home combines convenience with private outdoor living. The screened-in heated pool creates a central gathering space, while thoughtful features like a patio passthrough window from the kitchen make outdoor dining simple. With bikes for exploring the island, this home is set up for both convenience and flexibility throughout your stay.  👨 👧 Perfect For Families, couples, or small groups looking for a private pool home near Siesta Key Beach with easy access to dining, shopping, and island activities.  🎞️ Imagine This Start your morning with coffee by the pool as sunlight filters through the screened enclosure. Prepare breakfast in the kitchen and pass plates through the window to the patio, turning the space into an easy indoor-outdoor dining experience. After a quick 4-minute drive to Siesta Key Beach, spend the day on the sand before returning home to cool off in the pool or relax in the shaded outdoor seating area. In the afternoon, take the bikes out for a ride around the island or head into Siesta Key Village to explore local shops and restaurants. As evening sets in, fire up the grill for dinner, gather around the table indoors or out, and wind down in a space designed for simple, comfortable living.  🛌 Where You ll Sleep Bedroom 1: King Bed, Ensuite Bath Sleeps 2 Bedroom 2: Two Twin Beds Sleeps 2 Bedroom 3: Queen Bed Sleeps 2 Living Room: Queen Sleeper Sofa Sleeps 2  Accommodates up to 8 guests.  📍 Explore the Area 4-Minute Drive to Siesta Key Beach Powdery White Sand and Gulf Swimming Less Than 2 Miles to Siesta Key Village Dining, Boutiques, and Live Music 2.5 Miles to Crescent Beach A Quieter Stretch of Shoreline with Scenic Views 6.5 Miles to Downtown Sarasota Bayfront Parks, Arts, and Restaurants  📋 Don t Wait Your reservation includes peace of mind with our CottageClean program, featuring a six-hour deep clean and a detailed 35-point inspection prior to arrival.  Need to Know Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included. We happily welcome one small dog (up to 25 lbs) with a $250 per week pet fee breed guidelines apply to ensure a safe and comfortable stay for everyone. Please reach out prior to booking so we can help make your pup s stay just as wonderful as yours. The pool is heated from November 15th to April 15th. During cooler weather, heating performance may vary depending on outdoor temperatures. Per Sarasota ordinance, this property is limited to one rental per 30-day period. Reservations must comply with Sarasota County regulations.

Casa Del Mar - Luxury Home w/ Private Heated Pool!

🌴 Coastal Bliss in Siesta Key – Your Beach Escape Awaits! 🌊 Escape to paradise just minutes from Siesta Key Beach, consistently ranked the #1 beach in America and even #4 worldwide for its powdery white quartz sand and stunning turquoise waters. Whether you're seeking sun-soaked relaxation or an adventure-filled getaway, our charming retreat is your ideal home base. Enjoy a cozy, spacious, fully equipped home designed for comfort and ease. Perfect for couples, families, and groups. The space 🏡 **The Space** This cozy, spacious home has three bedrooms and a queen sleeper sofa, ideal for up to eight guests. Whether cooking, lounging, or entertaining, you'll have all the necessary space and amenities. 🍽️ **Fully Equipped Kitchen** Cook like you never left home: - Kitchen island with seating - Dining set & silverware for 8 - Coffee machine & Coffee Bar - Microwave, oven, air fryer combo - Toaster, blender, rice cooker, kettle - Dishwasher with soap dispenser - Placemats & full cookware - Complimentary coffee, sugar, cream & syrup 🍷 **Dining & Living Areas** - Dining table set for 8 - Relaxing living room with sofa & plasma TV - Decorative fireplace for cozy vibes 🎉 **Entertainment for Everyone** - **Board games, toys, ping pong & foosball tables** - **Bikes** to explore the neighborhood - Smart TVs in all bedrooms 🌴 **Outdoor Amenities** - **Jacuzzi** (use anytime at your own risk – rules provided) - **Barbecue grill** & utensils (please avoid use on turf) - **Front porch** sitting area - **Outdoor hose** to rinse off sand after the beach - **Driveway parking for up to 5 cars** 🛏️ **Bedrooms & Bathrooms** Master Bedroom:** - Extra-large space with King bed (12” hybrid mattress) - Flat screen TV, walk-in closet, and sitting area **Guest Room 1 - 1 Queen bed (12” hybrid mattress) - Custom closet, 32" flat-screen TV **Guest Room 2:** - 2 Twin beds (10” hybrid mattresses) - Custom closet, 32" flat-screen TV **Living Room:** - Queen-size sofa bed + bedding & pillows in master closet **Bathrooms:** - Spacious master shower - Shampoo, conditioner, body wash & hand soap dispensers - Hair dryer included 🧼 **Laundry & Cleaning** - Full-size washer & dryer (left side of house) - Detergent and softener provided 🏖️ **Beach & Storage** - Shed with **bikes, beach chairs, umbrellas & beach cart** 🛟 **Safety Essentials** - Fire extinguisher - Smoke & carbon monoxide detectors - First aid kit 👶 **Extras (No Extra Charge!)** - Pack and Play - Iron & ironing board - USB charging ports in master bedroom and queen bedroom - Starter supplies: toilet paper, dish soap, hand soap, sponge Make yourself home – anything in your way can be tucked away in one of the many closets for convenience. Whether you're here for a month or the season, this is the **ultimate Florida snowbird escape**. 🌞 Guest access Guests can have access to all spaces of the house, including the backyard, jacuzzi, laundry and storage room where all the beach gear and bikes Other things to note 🌴☀️COMPLIMENTARY FUN-ZONE! Grab it, enjoy it, and pop it back when you’re done 😎💫 🌊 Beach Bliss •	🚲 4 Bikes to cruise in style •	🏖️ 5 Beach Chairs for max chill •	⛱️ 3 Beach Umbrellas – shade like a pro •	🛒 2 Beach Cart – roll your beach day in •	🧸 Beach Baby Toys – fun for the little ones •	🤿 2 Snorkeling Set – discover underwater magic 🎯 Game Time Vibes •	🏓 Ping Pong Table – challenge accepted •	⚽ Football Table – spin to win! •	🎲 Table Games for cozy nights •	🥏 Flying Rings – let ’em fly •	🏐 Volleyball – bump, set, spike! •	🏈 American Football – toss it around •	🎯 Electronic Darts – aim high •	🌽 Cornhole Game – bean bag glory ☀️🌴 Have fun & make memories! Just return everything so the next guest can too. 🙌

Charm Beach House

🦩 Exclusive Amenities Include: • Private Screened in Heated Pool • Less Than 1 Mile From Siesta Key Village & Less Than 1.5 Miles From Siesta Key Beach Access 2 • Direct Canal Access • 3 Bedrooms, 2 Full Baths (Sleeps 8) • Covered Lanai and Outdoor Hammock • Outdoor Lounge area w/ HDTV, Fire Table, & Loungers • Filet Table Station • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials The space 🌴 Bali Hai House | Canal-Front Home with Private Heated Pool, Near Siesta Key Village  💖 Why You’ll Love This Home Bali Hai House places you on a quiet canal in Siesta Key, offering private waterfront views while remaining close to the island’s most popular spots. Located less than 1 mile to Siesta Key Village and under 1.5 miles to Siesta Key Public Beach Access 2, this three-bedroom retreat balances convenience with a peaceful residential setting. With a screened-in patio, private heated pool, and direct canal access, the outdoor spaces are designed for spending time together while staying connected to the water.  👨‍👩‍👧 Perfect For Families and small groups seeking a waterfront Siesta Key stay with private pool access and proximity to both the beach and village dining.  🎞️ Imagine This Start the morning on the screened patio overlooking the canal as wildlife moves quietly across the water. Brew coffee in the kitchen and plan the day, whether that means heading to Siesta Key Beach for a morning swim or strolling through Siesta Key Village for breakfast and shopping. In the afternoon, return home to cool off in the private pool or stretch out in the hammock while others gather around the outdoor seating area. Cast a fishing line directly from the canal’s edge or simply settle into a quiet moment by the water. As evening approaches, light the fire table and share laughs outdoors, or unwind inside in the comfortable living area before retreating to your private bedroom space.  🛌 Where You’ll Sleep • Bedroom 1: King Bed – Sleeps 2 • Bedroom 2: King Bed – Sleeps 2 • Bedroom 3: King Bed – Sleeps 2 • Living Room: Queen Sleeper Sofa – Sleeps 2  Accommodates up to 8 guests.  📍 Explore The Area • 0.8 Miles to Siesta Key Village - Dining, Boutiques, Coffee Shops, and Live Music • 1.5 Miles to Siesta Key Beach - Wide Sand, Gulf Swimming, and Beach Access • 3.6 Miles to Point of Rocks - Perfect for Snorkeling and Shelling • 5.0 Miles to Downtown Sarasota - Options for Restaurants, Shows, and Nightlife.   ⌛ Don’t Wait Your reservation includes peace of mind through our CottageClean™ program, featuring a six-hour deep clean followed by a detailed 35-point inspection prior to arrival.  🔎 Need to Know Per Sarasota ordinance, this property is limited to one rental per 30-day period. Reservations must comply with Sarasota County regulations. The pool is heated from November 15th to April 15th. During cooler weather, heating performance may vary depending on outdoor temperatures.

Bali Hai House Luxury Waterfront Home with Pool

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savings The space Discover your coastal home-away-from-home at The Nest on Siesta Key — a fully renovated, modern-luxury retreat located on peaceful street. Whether you're a snowbird looking to settle in for a sunny winter or a family in search of a high-end summer vacation, this 3-bedroom haven blends elegance, function, and coastal comfort with style. Bedrooms & Layout - King Master Suite – Bright and spacious with a large walk-in closet, dual-sink bathroom, and walk-in shower. A bonus flex room connects directly to the suite, offering a plush sofa and a NordicTrack bike — perfect for morning workouts with a pool view. - Guest King Bedroom – Thoughtfully styled and includes a smart TV, closet, and bright natural light. - Kid-Friendly Bunk Room – Features a twin/queen bunk, a separate twin bed, smart TV, and space for 3–4 kids to sleep comfortably. Open Living Space – Gather in the beautiful living room with a stone-accented fireplace, smart TV, and flexible couch sleeping option. Kitchen & Dining - Fully Stocked Gourmet Kitchen – All new appliances, stove, large fridge, dishwasher, microwave, and ample cookware. - Bar Seating + Dining – Barstools for 4 at the kitchen island + a formal dining table for 6. - Bonus Nook – A second dining table (seats 4) ideal for breakfast, reading, or remote work. Outdoor Living - Private Heated Pool – Surrounded by tropical landscaping, the perfect place to cool off and relax For added peace of mind, we’ve installed a pool door alarm as an extra layer of safety. (Note: Pool Heat is extra) - Covered Lanai – Dine with seating for 8, an outdoor smart TV, and shade for sunny afternoons. - Lawn Space – Ideal for little ones or pups to play. (Certain dog breeds okay, but note: one side of the yard is not fully fenced.) Location Perks - Quiet & Private – Located on the northern side of Siesta Key in a peaceful, upscale neighborhood. - Walk or Bike to the Beach – Just minutes to Siesta Key Beach, consistently ranked the #1 beach in the U.S. - Smart Features & Comforts – Smart locks, beach gear, high-speed WiFi, smart TVs, washer/dryer, driveway + garage parking. Quick Highlights - 2 King Bedrooms + Kid-Friendly Bunk Room - NordicTrack bike & private workout/flex space - Fully stocked kitchen + 2 dining areas - Smart TVs, smart locks, high-speed WiFi - Private pool & luxury outdoor dining - Walk to Siesta Key Beach - Certain breeds of dogs okay (yard partially fenced) - inquire for more information. Other information: - No smoking property - Pool heat extra - reach out for details. - No parties or large gatherings - This home is in a quiet residential neighborhood. We kindly ask that all guests treat the home and surrounding community with the same care and respect as they would their own. Whether you’re here for a month of sunshine or a week of seaside memories, The Nest is your private sanctuary on Siesta Key. Book your luxury island escape today! All pets must be approved so reach out to us first. Certain properties have weight and breed restrictions. For approved pets, there is an a nonrefundable pet fee of $300 plus taxes and processing fee per pet. Make sure to pick up after your dogs. IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions. Other things to note Please note that we may collect additional information from you after confirming your booking (usually an email address) in order to comply with local regulations and to provide the best possible experience.

"The Nest" Luxury 3BR, Heated Pool, Near SK Beach!

Beautifully remodeled home with pool located in the center of Siesta Key. The space HURRICANE UPDATE: HOME STAYED DRY! NO WATER INFILTRATION OR DAMAGE FROM HURRICANES!  NEW NEW!! UPDATED PHOTOS COMING SOON!  MODERN COASTAL meets funky boho at Chasin' Waves, a NEWLY REMODELED, OPEN CONCEPT home nestled on one of Siesta Key's most beautiful canopy tree-lined streets. The naturally lit bright space with trendy tropical color palette creates that well-needed feeling of serenity as soon as you step inside. Enjoy entertaining in the GREAT ROOM with large smart TV, leather sectional, dining table with seating for 8, luxury vinyl plank flooring and generous pool views.  And speaking of POOL VIEWS — GORGEOUS NEW TRAVERTINE pool and lanai decks, along with a NEWLY-SCREED POOL CAGE and new pebble pool surface, complete this upscale paradise.  A UNIQUE and FABULOUS feature is the ability to make the entire home TOTALLY SCREENED-IN due to the front screened lanai and back pool cage. Slide open the front and back large glass pocket doors and enjoy the gulf breeze with virtually bug-free living!  Large GOURMET KITCHEN boasts a gorgeous 10' quartz island with seating for 6, all new stainless-steel appliances including that hard-to-find GAS range, and stainless-steel wine refrigerator.  Popular SPLIT FLOOR PLAN with 3 bedrooms and 2 bathrooms can accommodate up to 8, including trundle bed in office area where new barn doors have been installed for privacy.  Two options to WORK REMOTELY. Enjoy pool views from your home office area or surf the web from the alternate desk area in the screened-in lanai. High-speed internet service to keep you connected.  Large screened in caged pool with added optional baby security gate. Fun tiki bar, outdoor dining table and chairs, chaise lounges, and Weber gas grill.  Oversized driveway with new pavers, mango trees and tropical landscaping complete this island oasis. Welcome binder with local information makes getting acclimated to island life a breeze.  All NEW interior furniture, bedding, décor, washer and dryer, whole-house updated A/C and pool heater.  BEACH SUPPLIES including beach towels, beach wagon, umbrella, 8 chairs and a cooler.  BEDROOM #1: King Bed – Sleeps 2 --Smart TV and walk-in closet. Remodeled ensuite bathroom with tiled tub/shower and flooring, marble vanity and double bowl sinks  BEDROOM #2: Queen Bed – Sleeps 2 – Smart TV and walk-in closet. Large sliding door access to screened back lanai  BEDROOM #3: 2 Twin Beds – Sleeps 2 - Smart TV and closet. Small desk w/chair  OFFICE AREA: Twin daybed w/twin pull out trundle – Sleeps 2. Newly installed barn doors for privacy.  2nd Bathroom remodeled with large, tiled shower and flooring, marble vanity and double bowl sinks.  Pack ‘n Play and Highchair available for use at the home.  Consistently voted the #1 beach in the country, this home is only a 4-minute drive/bike ride to the powdery-white sand of Siesta Key beach. Enjoy a day at the beach, new children's shaded playground, pickleball, tennis or volleyball courts or stroll into the village with shops, restaurants, bars w/live entertainment. Multiple free taxis and golfcart services (tips only) make this centrally located home hard to beat! Drive over the bridge to the mainland and enjoy downtown Sarasota's restaurants, galleries, and nightlife bustling with culture and ­­­­­activities.  Just bring your toothbrush, swimsuit, and flip flops because at Chasin' Waves you will have most everything you need for easy island living. You may never want to leave!  Home is Monthly Rental Only, must stay at least 30 nights consecutively.   NO SMOKING.  Pool Heating: $25/night for stays of 21 nights or less and $15/night for stays over 21 nights. Guest access Check-in instructions will be email 1 week prior to your arrival date.

Newly Remodeled Home w/ Pool in Siesta Key

🦩 Exclusive Amenities Include: • Private Heated Pool (Seasonal) • Direct Canal Access with 3 Kayaks • 0.7 Miles to Siesta Key Beach • 1.4 Miles to Siesta Key Village • Screened-In Lanai with Lounge + Dining • Gas Grill & Outdoor Dining Area • King Primary Suite with Canal Views • Gourmet Kitchen with Keurig + Essentials • 4 HDTVs & Free High-Speed WiFi • In-House Washer/Dryer • Beach Towels, Chairs, Cooler & Caddy • CottageClean™ Certified for Enhanced Cleanliness The space 🌴 Sand Dollar Cottage | Canal-Front Oasis + Private Heated Pool  💖 Why You’ll Love This Home Float into coastal serenity at this canal-front escape on Siesta Key. Paddle from your private dock, dine in the screened lanai, or cool off in the private heated pool—all just a 15-minute walk to Siesta Key Beach. This home blends laid-back luxury with island charm.  👨‍👩‍👧 Perfect For Ideal for families, couples, or groups looking for a peaceful waterfront retreat near the beach and vibrant Siesta Key Village  🎞️ Imagine This You wake to the gentle shimmer of water just outside your window. Brew a cup from the Keurig, then sip it poolside as the sun rises over the canal. After breakfast in the screened lanai, grab a kayak and explore quiet mangrove-lined waterways. Back at home, rinse off in the outdoor shower, then stroll 0.7 miles to Siesta Key Beach for a sunny afternoon on the powdery sands. Return in time for sunset cocktails by the pool or grill up a fresh catch and gather around the dining table to recap the day’s adventures. When night falls, settle into plush beds or stream a movie on one of four HDTVs—ready to do it all again tomorrow.  🛌 Where You’ll Sleep Bedroom 1: King Bed, ensuite bath, ground floor, canal views, TV Bedroom 2: Queen Bed, shared bath, ground floor, TV Bedroom 3: Two Twin Beds, shared bath, ground floor, TV Additional: Two portable cots in bedroom closets (linens provided)  📍 Explore the Area • 0.7 miles to Siesta Key Beach • 1.4 miles to Siesta Key Village – restaurants, boutiques, live music • Easy walk or bike to shops, cafes, and island market • Nearby kayak routes, fishing spots, and island shuttle pick-up • Peaceful residential street with relaxed, coastal energy  📝 Don’t wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program - a 6-hour deep clean and 35-point inspection.  ✨ Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free high-speed WiFi included. This pool is heated between November 15 - April 15. If any guest has difficulty with stairs, please contact us for alternative accommodations. Sarasota ordinance allows one rental per 30-day period—contact us with questions before booking.

Sand Dollar Cottage | Waterfront Home w/ Pool!

Welcome to the "Sand Dollar Inn"! Built in 2000, this is the perfect family friendly home that sleeps 8 and is a 4 minute short walk to the Village/ Siesta Market and 9 minute walk to the beach! The private back yard of this light and bright home is a tropical paradise with a private heated saltwater pool and spa. You will find everything you need to make your stay unforgettable from the large assortment of bikes, beach toys, tents and chairs to gourmet cookware in the gourmet kitchen. The space Light and bright beachy single family home fully equipped to make you feel totally at home. All the comforts of home including gourmet cookware and appliances. 10+ bikes of all sizes get you to SK's white powder sand fast plus beach chairs and other gear to make it easy when you get there. We have super fast internet and a dedicated work space with desk, chair and new computer monitor in the cabana room off the pool area. With the super-fast WiFi you'll be all set for remote work-from-the-beach! Guest access Parking for 1 car in the spacious garage and 4 in the driveway Other things to note Screened in 2 story porches offer an inside out lifestyle. Open the french doors to the porch and let the breeze blow through the house while looking out to the pool.

Pool & hot tub -Walk to Beach!

Enjoy Siesta Key to is't fullest with this well appointed house. This house sits right on a canal with water access so you can enjoy kayaking and paddle boarding at your leisure. Also outside is and outdoor fire pit and a screened in pool that is heated so you can enjoy year round. Once you step inside this beautiful house you are greeted with a bright and airy beach theme that extending into the kitchen with white cabinets and marble countertops.

Vintage Coastal

Exclusive Amenities Include: • Private Heated Salt Water Pool & Spa • Waterfront Home w/ Unbeatable Views • Canal Access & Views • 1 Mile from Siesta Key Beach • 3 Bedrooms, 2 Full Baths • Covered Back Patio, Corn Hole, Ping Pong Table • 2 Kayaks & 2 Paddle Boards • Dog-Friendly with a Fee (2 small dogs up to 25lbs, not quoted in price & charged after approval) The space 🌴 Blu Sky Cottage | Waterfront Pool Home, Resort-Style Backyard, Near Siesta Key Village  💖 Why You’ll Love This Home Blu Sky Cottage stands out for its rare combination of waterfront access and a resort-style backyard, offering a one of a kind setting on Siesta Key. The outdoor space is the true highlight, with a private saltwater pool and spa overlooking the canal, creating a seamless connection between relaxation and activity. The backyard is designed for both lounging and play, with space for outdoor dining, grilling, and games, all set against the water. With direct canal access, guests can utilize the complimentary kayaks and paddleboards, or bring a small boat and head out right from the property. Inside, the home features an open-concept layout with comfortable living and dining areas, along with a dedicated workspace complete with a printer for added convenience during longer stays.  👨‍👩‍👧 Perfect For Families or small groups looking for a waterfront stay with standout outdoor space, easy access to Siesta Key Village, and room to unwind between beach days.  🎞️ Imagine This Spend the morning out on the water, launching a paddleboard or kayak directly from the backyard. Return home to cool off in the pool or relax in the spa while overlooking the canal. Afternoons are easy here, grill lunch outside, gather around the shaded dining area, or play a casual game of cornhole in the yard. As the day winds down, head into Siesta Key Village for dinner or stay in and enjoy the quiet waterfront setting.  🛌 Where You’ll Sleep • Bedroom 1: King Bed • Bedroom 2: King Bed • Bedroom 3: Queen Bed + Twin Bunk Bed  Accommodates up to 8 guests.  📍 Explore the Area • 1.0 Mile to Siesta Key Beach – Powdery white sand and Gulf waters • 0.5 Miles to Siesta Key Village – Restaurants, shops, and nightlife • Canal Access – Paddleboarding, kayaking, and boating from the property  ⌛ Don’t Wait A rare Siesta Key find due to its waterfront setting and standout outdoor space, Blu Sky Cottage offers a resort-style backyard experience paired with a prime Siesta Key location. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.  🔎 Need to Know Per Sarasota County regulations, this property allows one rental per 30-day period. Please contact us for more information. The pool is heated between November 15th and April 15th. Cooler temperatures may impact heating performance. Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included. We happily welcome 2 small dogs (up to 25 lbs) with a $250 fee per pet—breed guidelines apply to ensure a safe and comfortable stay for everyone. The primary guest making the reservation must be at least 26 years of age.

Blu Sky Cottage | Waterfront Home w/ Private Pool

Waterfront luxury in the heart of Siesta Key. This 3-bed, 2-bath private pool home offers a rare combination of canal-front serenity and walk-to-beach convenience. Enjoy a private boat dock with direct Gulf access, kayaks you can drop in your backyard, relax on the sunlit lanai, and unwind with tranquil water views (spot manatees!). Just minutes from Siesta Key Beach, dining, and village shops—this is coastal Florida living done right. Bikes, Kayaks, Golf Clubs, and Beach Supplies all provided! The space WATERFRONT | PRIVATE POOL | PRIVATE DOCK | BIKES & KAYAKS | MINUTES TO SIESTA KEY BEACH Welcome to one of the most sought-after setups on Siesta Key—a canal-front, 3-bedroom pool home where you can walk to the #1 beach in the U.S., launch kayaks from your backyard, and park your boat at the house with direct access to Sarasota Bay and the Gulf. This 3-bed, 2-bath waterfront retreat sleeps up to 8 guests and combines the relaxed luxury of island living with unbeatable access to boating, beaches, dining, and Siesta Key Village. 🚨PLEASE NOTE: There may still be ongoing construction at the neighbors house. As a result, there may be construction noise and materials. It can sometimes get very loud. We also cannot control whether neighbors choose to initiate construction/renovation projects. As a result - we do not issue refunds due to construction, construction noise, or amenity closures. What Guests Love (from our reviews!): ⭐ “Beautiful home that felt like home” ⭐ “Even better than expected” ⭐ “Fished off the back dock and kayaked right from the house” ⭐ “Super clean, amazing pool, and incredible scenery” ⭐ “The team was responsive and went above and beyond” ✅ Why Book Our Home: ✔ RARE walk-to-beach + PRIVATE BOAT DOCK combination (no cost to park) ✔ Private pool with covered lanai overlooking the canal ✔ Direct boating access—bring your boat or enjoy the kayaks (we provide kayaks!) ✔ Quiet WATERFRONT neighborhood, minutes from Siesta Key Village ✔ Bikes, kayaks, pool, dock—everything included, no add-ons SLEEPING & COMFORT ✓ 3 bedrooms: 2 King beds + 1 Queen bunk bed ✓ Sleeps up to 8 guests comfortably ✓ Hotel-quality linens, extra pillows, and hangers ✓ Central air conditioning and heating throughout BATHROOMS ✓ Primary ensuite with dual sinks and walk-in shower (no tub) ✓ Second bathroom with Jack & Jill layout and tub/shower combo ✓ Towels, toiletries, and hair dryer provided KITCHEN & DINING ✓ Fully equipped kitchen with dishwasher, oven, range, microwave, refrigerator, freezer, and kettle ✓ Cookware, utensils, and dining essentials included ✓ Indoor dining plus outdoor grill for poolside meals ✓ Keurig & Coffee provided ENTERTAINMENT & AMENITIES ✓ Comfortable living area with TV and high-speed Wi-Fi ✓ Private large screened POOL with solar heating 🏊‍♀️Guests are not permitted to access or adjust the pool heater themselves. If you would like the pool heated, please request it at least 72 hours in advance. Pool heating is available for an additional fee of $45 per day, and the owner will activate it remotely. Unauthorized use or activation of the pool heater without advanced notification will result in additional fees. ✓ Covered lanai with seating and canal views ✓ Private dock with lift, plus kayaks ready to launch ✓ Ideal for boating, fishing, swimming, and relaxing outdoors ✓ Bikes provided FREE for guests! PARKING & LOCATION ✓ 2-car garage plus driveway parking ✓ Short walk to Siesta Key’s world-famous white-sand beach ✓ Minutes to restaurants, cafes, bars, and shops in Siesta Key Village ✓ Peaceful canal-front setting with quick access to open water Guest access Guests have full access to the entire home 🏡, including the private pool 🏊, lanai ☀️, boat dock, outdoor seating 🍹, kitchen 🍳, laundry 🧺, and 2-car garage 🚗 — all just minutes from Siesta Key’s beaches 🏖️ and village shops 🛍️ Other things to note ⏰ Check-in / Check-out: Standard check-in and check-out times are in place to allow our cleaning team to prepare every unit to our 5-star standard. Early check-in may be available upon request—just send us a message! Note, there is a per hour fee! ⚠️ A digital rental agreement MUST be signed prior to arrival, and you will need to provide a copy of a legal ID with a verification selfie. This cannot be done in person. ⚠️ Damage Waiver: Every reservation includes our Damage Waiver Program — you’re covered for up to $500 in accidental damage during your stay. Just relax and enjoy your trip, knowing little mishaps are taken care of. (Note, this is not insurance and does not replace travel or liability insurance; this self-funded protection covers up to $500 in accidental damage to contents only; examples included linens, towels, and wine. 🐜 Pest Note: We treat regularly, but Florida may have occasional pests. No refunds are issued for pest sightings, though we’re always happy to address concerns. ⚠️ Please be aware that certain situations beyond our control may occur, including construction or noise outside the unit, temporary closure of amenities, utility or city repairs, or other issues on neighboring properties or units. As these circumstances are beyond our control, we are unable to provide refunds for any related inconveniences resulting from these factors. 🚼 Pack ’n Plays must be requested in advance and are subject to availability. As these items are shared across our units, we kindly ask that you request one, at the time of booking to confirm availability. Please note that not all listings include them, so we recommend checking the amenities list or reaching out to our team in advance for confirmation. PLEASE NOTE: 🗑️Additional supplies may be available upon request but are not guaranteed. If you run out, nearby stores are easily accessible. Towels are provided for approximately the first 2–3 days of your stay—please use the in-unit washer and dryer if available to refresh them. If your unit does not include laundry, on-site facilities may be available (fees may apply). For stays of 5 nights or longer, you may request replacement towels, subject to availability. Please note that not all listings include laundry, so we recommend checking the amenities or reaching out to our team in advance to confirm. ✓ ITEMS LEFT BEHIND. If a guest leaves personal items behind and requests their return, they are responsible for a $25 service fee plus packaging and shipping costs. We are not responsible for any loss or damage to left items once the guest has departed.

Siesta Key Waterfront House + Pool & Boat Dock!

The Inn is conveniently located on Siesta Key directly across the street from the Beach. Its guests enjoy beach access right across the road ( access #9 ). Siesta Village is also just a 5-minute walk from the Inn. If walking is not an option there is a trolley that is free of charge to ride and get around the Key. We have 6 individual Cottages in total that range from a one bedroom units to a three bedroom units. The space Immerse yourself in historic Florida beach life with this one-of-a-kind accommodation! No other hotel or resort room can come close to the old Florida charm of The Cottage. Built in 1936, The Cottage graces the front portion of 515 Beach Rd. A lovely 20′ x 20′ screened in porch is the entryway to this fabulous Vintage Florida Beach House. As you walk through the two French glass doors, you are greeted by the gorgeous vaulted ceiling, pecky cypress paneling. The focal point in the living/great room area is a beautiful natural stone fireplace. The mantelpiece now hosts a 65″ flat screen TV . Guest access Access to whole space this is a private unit. You also have a private outside space with outdoor furniture. The pool area is shared with the 6 individual units along with the beach equipment area.

Beach house W/Heated Pool across street from beach

This is a thoughtfully renovated canal-front residence near Siesta Beach. A private pool and screened patio offer a refined and tranquil retreat with direct canal views. Bright interiors and carefully curated details create an atmosphere of timeless, understated luxury. Just an 8-minute walk from the world-famous beach, yet surrounded by complete peace and privacy. This home is designed for guests who appreciate discreet luxury and elevated comfort. The space HoHome & style Spacious, stylish interiors with modern design and bright, airy spaces Private garden and outdoor relaxation area with a heated pool, perfect for morning coffee or peaceful evenings Fully equipped kitchen, ideal for both short and extended stays Pet-friendly home, because vacations are better with the whole family Location & distances Siesta Beach: 2-minute drive or approximately 8-minute walk Downtown Sarasota & St. Armands Circle: approximately 20 minutes I-75 highway: approximately 10 minutes SRQ Airport: approximately 30 minutes / Tampa International Airport: approximately 60 minutes Sleep & comfort 3 luxury KING beds plus a Queen sleeper sofa Premium linens for restful sleep Fast, reliable WiFi, ideal for work and streaming Washer and dryer on-site Beach essentials provided: chairs, towels, umbrella Two-car garage Contactless check-in and check-out for a seamless arrival This home is ideal for guests who want to enjoy luxury-level comfort for their vacation, with the added benefit of a heated pool, while staying close to the beach and Sarasota’s most popular destinations. Guest access This property has an active Ring doorbell We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. 2 cars maximum can park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. Other things to note This property has an active Ring doorbell We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. 2 cars maximum can park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. Pool Heating – Important Information The pool is heated up to 80°F, which is comfortable for most guests and included as standard. If you would like the pool heated above 80°F, an additional fee of $35 per day applies. Please note that we do not heat the pool when outdoor temperatures are below 70°F, as it becomes impractical and uncomfortable to use. Pool heating is turned on one day prior to your arrival, so the water is ready for you when you check in. Important note about Florida conditions: Due to Florida’s climate and environment, it is normal that insects such as ants or cockroaches may occasionally appear. This is more common during rainy periods, but can happen at any time. To help prevent ants, please do not leave food out and store all food in sealed containers or in the refrigerator. However, we cannot guarantee that previous guests have followed these guidelines, so occasional ants may still appear. The property is regularly treated for pest control, but throughout Florida it is common that an occasional insect may still be present. Please understand that the presence of insects does not qualify for a refund or for any partial refund related to early check-out. Smoking of any kind is prohibited indoors. Violation results in a $300 additional cleaning and deodorizing fee.

Luxury Canal-Front Home + Heated Pool Near Beach

Welcome to your perfect Florida getaway! This beautifully remodeled single-family home features 3 spacious bedrooms and 2 modern bathrooms, ideal for families or groups looking to relax in style. Step outside and enjoy your private 27' x 13' heated pool, set to a comfortable 82 degrees year-round. The pool includes a sunshelf, perfect for lounging in the water with a cocktail or even enjoying dinner alfresco right in the pool! The space 🏡 Welcome to Your Perfect Vacation Getaway! Welcome to your perfect vacation getaway! This beautifully remodeled single-family home features 3 spacious bedrooms, 2 modern bathrooms, and everything you need for a relaxing and memorable stay. Parking: You’re welcome to park in the driveway, which accommodates up to two cars, or you may also park on the street if needed. Just a short walk to over 15 restaurants, 12 bars, boutique shops, bike/scooter rentals, wash & fold services, and more. 🏖️ Beach Life Made Easy: The local beach is just 3 blocks away – an easy, beautiful walk. The famous Siesta Key Beach, voted one of the Top 10 Beaches in the World (Travel Channel), is a short drive away. 🎯 Nearby Attractions: Enjoy a short drive to local golf courses, cultural sites, nature trails, and more – this area is packed with things to see and do! Whether you're soaking in the sun on the pool shelf, exploring local hot spots, or relaxing indoors, this home is designed for comfort and fun. ⚠️ Important Information & House Rules: -Please note that we do not provide beach chairs, umbrellas, towels, or toys. -The pool is professionally cleaned once a week. However, due to Florida’s weather (rain, wind, etc.), debris may occasionally enter the pool between cleanings. A pool net is provided for your convenience to help keep the water clear during your stay. -The home's temperature is set to a comfortable 72°F and cannot be adjusted. Please be aware that there are no ceiling fans in the home. -This is a family-oriented home, and we do not allow Spring Break groups or parties. Primary renter must be at least 25 years old – no exceptions. -Quiet hours must be respected, and we ask all guests to treat the home and neighborhood with care. As per Gracie Johanna review: Very impressed with the level of service. The team is reliable, detail-oriented, and always available when I have questions. Highly recommended for rental property management. Other things to note Here are the important policies and guidelines to note for your stay: Check-in: We facilitate self-check-in, and guests are welcome to check in any time after 4 pm Check-out: We kindly ask that you check out on or before 11:00 AM on your departure date. This allows us enough time to clean and prepare the property for the next guests. No dishwasher available, so we kindly ask that you wash the dishes before checkout. No Smoking: Smoking is strictly prohibited inside the house and within any common areas of the complex. Please respect this policy to maintain a clean and smoke-free environment. No Parties: The house is intended for quiet and peaceful stays, and hosting parties or large gatherings is not allowed. Please be considerate of the neighbors and keep noise levels to a minimum, especially during nighttime hours. Pets allowed: Please inform us in advance if you plan to bring pets. Pet Policy: We are delighted to welcome your pets to our property. To ensure a comfortable experience for both you and your furry companions, please review our policy and fees: Please ensure that your pet is well-behaved and cleaned up both indoors and outdoors. A pet fee of $50 per pet and a $200 refundable deposit is required. These policies are in place to ensure a comfortable and enjoyable experience for all guests and to maintain the integrity of the property. We offer early check-in or late check-out for an additional fee of $25 per hour Early check-in: 2pm Late check-out: 1 pm If you have any questions or need further clarification about these policies, please contact us. We want to ensure that your stay is pleasant and in accordance with these guidelines.

Island home in paradise

This beach house is located along a quiet, meandering street dotted with palm trees, and is just 300 steps or approximately a 3 minute walk to Siesta Key’s Beach Access #7 and a short 3-4 minute stroll to the village for shopping, dining, and entertainment. Our Condo has a balcony overlooking the pool area, this 3-bedroom home has Vaulted ceilings, an open multilevel floor plan, and breezy beach décor contribute to the space’s fresh, serene feel. The space Upon entry, immediately ascend to the main (second) floor. In the master bedroom, located on this main floor, you will find a king-sized bed with quality linens. An updated full bath is conveniently situated next to the master bedroom. Also on the main floor, the kitchen is equipped with modern cabinets, granite countertops with a sleek tile backsplash, and stainless steel appliances. Adjoining the kitchen is the dining area, which comfortably seats six and opens up to the great room. This spacious living area features sliding glass doors that open up to the balcony and 20-foot ceilings with ceiling fans. The flat screen TV features cable with upgraded sports packages and a dvd player. Stairs lead up to the top floor, where there are two more well-appointed rooms—one with a king-size bed and the other with two queen-size beds. Between the rooms is a full bathroom with a tub/shower combo. A paved walk borders the driveway and leads to the home’s private entrance. Continue following the path to access the secluded, shared pool area and private cabana, it's own dining table and chairs, and barbecue grill.

Pool Walk to the Village & Beach 3 bed 2 bath

This beach house is located along a quiet, meandering street dotted with palm trees, and is just 300 steps or approximately a 3 minute walk to Siesta Key’s Beach Access #7 and a short 3-4 minute stroll to the village for shopping, dining, and entertainment. Our Condo has a balcony overlooking the Grand canal , this 3-bedroom home has Vaulted ceilings, an open multilevel floor plan, and breezy beach décor contribute to the space’s fresh, serene feel. The space Upon entry, immediately ascend to the main (second) floor. In the master bedroom, located on this main floor, you will find a king-sized bed with quality linens. An updated full bath is conveniently situated next to the master bedroom. Also on the main floor, the kitchen is equipped with modern cabinets, granite countertops with a sleek tile backsplash, and stainless steel appliances. Adjoining the kitchen is the dining area, which comfortably seats six and opens up to the great room. This spacious living area features sliding glass doors that open up to the balcony and 20-foot ceilings with ceiling fans. The flat screen TV features cable with upgraded sports packages and a dvd player. Stairs lead up to the top floor, where there are two more well-appointed rooms—one with a king-size bed and the other with two queen-size beds. Between the rooms is a full bathroom with a tub/shower combo. A paved walk borders the driveway and leads to the home’s private entrance. Continue following the path to access the secluded, shared pool area and private cabana, it's own dining table and chairs, and barbecue grill.

Heated Pool 3 bed 2 bath walk to village and beach

Spend your vacation relaxing in this lovely 3-bed, 2-bath townhome. On the ground level, you will find parking for up to 2 cars. The second level hosts a spacious living room, dining, and kitchen areas. You will also find a powder room and the first balcony for enjoying the ocean view. The 3 bedrooms, 2 full bathrooms, and second balcony are located on the third level. This home is adjacent to beach access #10 – perfect for taking a trip down to Siesta Beach! The space The kitchen offers plenty of storage and stainless countertops. The living room offers space for the entire family to relax with large windows looking out towards the beach. On this floor, you will also find a powder room and the first of two balconies for enjoying the fresh island breeze and ocean view. The 3 bedrooms, 2 full bathrooms, and second balcony are located on the third level. Located within walking distance to Siesta Key Village, this home is adjacent to beach access #10 – perfect for taking a trip down to Siesta Beach or enjoying a stunning view! Bedroom 1 – King Bedroom 2 – Twin over Queen Bunk Bed Bedroom 3 – King and Twin Bunk Bed Living Room, Kitchen, Dining Area, 2 Balconies, and Outdoor Seating Area The Location: - Directly next to entrance of Public Beach Access #10 - 0.5 Miles to Siesta Key Village - 2.1 Miles to Crescent Village - 0.5 Miles to Pool Access - Directly next to local free trolley stop. Siesta Key has 13 beach access points and a free trolley system making all of Siesta Key easily accessible no matter where you are on the island! Other things to note - This property is stairs only; all guest must have the ability to climb stairs. - Check-in is located at our office off site of the property. The address will be shared with check-in instructions. - Security Authorization Hold taken upon check-in: $1,000. This hold is released upon inspection of unit after check-out or charged for damages found to the unit. - To book a beachside managed Property Between February 1st and April 15th, the booker must be 27 years old or older and be present for the entire duration of the stay. Outside of this time frame, the standard minimum age for this property applies. Added Amenities Included in Your Stay: - Free Wifi - Beach Chairs, Beach Towels, Beach Wagon, and Beach Cooler, - Partner Property Pool/Hot tub Access, - Complimentary Bicycles Rentals located at Partner Property, - 7-days a week, Beachside Management office is open for your convenience and guest needs with after-hours support!

Stunning 3Bed Steps from Siesta Key Beach Access!

Escape to luxury in our serene Sarasota home! - Private saltwater pool and hot tub for relaxation. - Open-concept living area with natural light. - Three cozy bedrooms designed for comfort. - Fully-equipped kitchen with stainless steel appliances. - Spacious backyard with BBQ grill and free bikes. - Prime location: 3 min drive to Siesta Beach. - Experience a High-End Vacation Getaway in Sarasota! The space Escape to luxury in our serene Sarasota home! Relax in your private oasis with a sparkling pool, hot tub, and expansive backyard. Enjoy the open-concept living area and three cozy bedrooms designed for ultimate comfort. Experience a High-End Vacation Getaway in Sarasota! Key Features: Comfortable Accommodation: - 3 Spacious Bedrooms: - Primary Bedroom: King-sized bed, skylight, desk, reclining chair, and a large flat-screen HDTV with streaming services. - Second Bedroom: Cozy queen-sized bed with backyard views. - Nautical Room: Two comfortable full-sized beds and a wall-mounted TV. Interior Feeling: - 2 Modern Bathrooms: - Both bathrooms feature walk-in showers, beautiful tilework, and are stocked with fresh towels and hair dryers. - Fully-Equipped Kitchen: - Stainless steel appliances, bar-style island, wrap-around countertops, and all the essentials for a home-cooked meal. - Comfortable Lounge Area: - Large flat-screen HDTV with streaming services, natural light from skylights, and a relaxing space for everyone to unwind. - Dedicated Workspace: - High-speed WiFi and a desk for remote work or planning your vacation activities. Outdoor Bliss: - Resort-Style Outdoor Space: - Private Pool + Hot Tub: Perfect for relaxation and enjoyment. - BBQ Grill + Outdoor Dining Area: Ideal for outdoor meals. - Sunny Patio with Loungers: Perfect for sunbathing or reading a book. - Spacious Fully-Fenced Backyard: Great for family fun and games. - Free Bikes: Explore the local area and nearby beaches. Parking: - Free Street Parking + EV Charger: - Convenient parking options and electric vehicle charging. Delightful Dining: - Spacious Indoor Dining Area: - Elegant six-seater dining table for family meals and gatherings. Prime Location: - 3 Min Drive to Siesta Beach - 10 Min Drive to Crescent Beach - 13 Min Walk to a Local Beach - Easy access to Siesta Key Village and local restaurants. Why You’ll Love Staying Here: - Private Pool and Hot Tub: Perfect for relaxation and family fun. - Modern Comforts: Enjoy high-speed Wi-Fi, a large flat-screen TV with streaming services, and a fully-equipped kitchen. - Convenient Location: Quick access to Sarasota’s best beaches and local attractions. - Family-Friendly: Spacious backyard, BBQ grill, and free bikes for exploring. Book Your Stay at This Gorgeous Sarasota Home Today! Guest access The entire property is exclusively yours during your stay, so relax and make yourself at home. You will have access to the entire house, backyard, pool, and all listed amenities. In addition to the spaces mentioned above, your stay includes: 	• High-Speed Wi-Fi 	• Free on-site parking & an EV Charger 	• Complimentary Bicycles & a Kayak 	• Private Laundry Room with Washer & Dryer 	• Air Conditioning & Heating 	• Children's Amenities (Crib, High Chair, Pack & Play, etc.) Other things to note Here are the important policies and guidelines to note for your stay: Check-in: We facilitate self-check-in, and guests are welcome to check in any time after 4 pm Check-out: We kindly ask that you check out on or before 10:00 AM on your departure date. This allows us enough time to clean and prepare the property for the next guests. No Smoking: Smoking is strictly prohibited inside the house and within any common areas of the complex. Please respect this policy to maintain a clean and smoke-free environment. No Parties: The house is intended for quiet and peaceful stays, and hosting parties or large gatherings is not allowed. Please be considerate of the neighbors and keep noise levels to a minimum, especially during nighttime hours. Pets allowed: Please inform us in advance if you plan to bring pets. Pet Policy: We are delighted to welcome your pets to our property. To ensure a comfortable experience for both you and your furry companions, please review our policy and fees: Please ensure that your pet is well-behaved and cleaned up both indoors and outdoors. A pet fee of $50 per pet and a $200 refundable deposit is required. These policies are in place to ensure a comfortable and enjoyable experience for all guests and to maintain the integrity of the property. We offer early check-in or late check-out for an additional fee of $50 Early check-in: 2pm Late check-out: 12 pm If you have any questions or need further clarification about these policies, please contact us. We want to ensure that your stay is pleasant and in accordance with these guidelines. We require notice and payment to heat the pool 48 hours before check-in. An additional fee of $50/night to heat to 85 degrees There is a two-day minimum for heating the pool. Sarasota Beach: approximately 0.8 miles away (15–17 minute walk) Siesta Beach: approximately 0.7 miles away (15-minute walk or 4-minute drive) Your Host, Siesta Key Property Management

Siesta Key Oasis Walk to Beach, Pool, Hot Tub, BBQ

The Oceanview Penthouse 603 Oceanview Penthouse, 12-steps to Siesta’s best beach! Stunning views with floor-to-ceiling “movable’ glass walls in bedroom and living area. Just 3-min by trolley or bike to Siesta Village. Remodeled in 2023. Free bikes and paddle boards. Communal lounging, alfresco dining, ping-pong, and Tiki bar. Perfect for families or couples looking to relax explore repeat. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta The space What Guests Love ∙ Ocean Views – southwest views of Gulf and sunsets through floor-to-ceiling windows ∙ Gulf Breezes – wall of windows folds for unobstructed ocean breezes day or night ∙ It’s a Penthouse –no neighbors above or next to you and best views at property ∙ Beaches – 12-steps to access of Americas top beach, white sand and calm clear water ∙ Relaxing – safe easy access to outside attractions and lots of plus-space on site ∙ Sunsets –walk 30-seconds to best sunsets or just enjoy from your living room ∙ Island Trolley –picks up out front, free of charge to all attractions and welcome’s drinks ∙ Activities – free bikes and paddleboards provided, scooter and golf cart rentals nearby  ∙ Extra Spaces –ping pong room, alfresco dining-lounging, DIY tiki bar in the back ∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch ∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts ∙ The Memories – walk to all Siesta Key's top attractions and guaranteed fun for all   The Beach Our beach access is across the street, 12-steps, and is quieter and more private. Although one of the most desirable on the Siesta Key and has no parking available so isn’t easy to access from rentals outside the neighborhood. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. A livelier beach scene with food, drinks and even a weekend drum circle is accessible a 5-to-10-minute walk south on the beach.   The Home Ocean view property contains just 3 units and was remodeled in 2022. The penthouse unit has the best views, sun and breezes. It also doesn’t share a wall or ceiling with another unit. Floor to ceiling glass walls in master bedroom and living area create wide-open southwestern exposures. Glass wall is bifold design and fully opens for maximum ocean or sunset views and refreshing breezes day and night. Common areas include the ping-pong room, tiki bar, alfresco dining, and usually cornhole. Set on the Southern edge of Siesta Village and surrounded by tropical plants. Just 10-second walk to top beaches, and 3-minute golf cart or trolly ride (10-minute walk) to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.   Bedroom Details This ocean view penthouse unit is 3BR and is two staircases from the ground. There is one large king bedroom, an ocean view queen bedroom, and a bunkroom with twin-over-full and twin-over-twin-bunks. Tempur-pedic rollaway beds are available with advance notice, and although the master bedroom is quite big, setting up by the window in the living room makes it the best sleeping area in the house. You can sleep up to 9 family style. Need more space? Ask about an additional unit nearby.   Beach Gear Provided We provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide "snorkeling gear" but this and anything you need can be rented or purchased nearby.   Household Items Provided We provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.   What to Bring It’s a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.   History – There’s no public parking in this area so, even though this is a gorgeous beach, it ends up being a little more private than most. When I was a kid growing up on Siesta Key, this beach access was called “Palm Island” and named after the island of the same name right at the end of the street. The island has a small bridge going to it and is literally a “heart shaped” island within the island of Siesta Key. When I was younger this was our lovers lane and, for me, it’s still the spot to fall in love or rekindle an old flame.    Post Booking Support We understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time.    Terms Payments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.   Travel Insurance If you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Gertrude Siesta | Oceanview Penthouse Beach 1-min!

Coastal Charm by Tropical Sands Accommodations Welcome to Coastal Charm, a refreshed 3-bedroom, 2-bath Siesta Key home located just a 10-minute walk to Siesta Key Beach and close to the shops and restaurants of Siesta Key Village. This peaceful canal front property features a private pool, outdoor dining, and dog friendly options. Perfect for families and small groups seeking a long-term stay on Florida’s most beloved barrier island. With a 30-night minimum stay, it’s ideal for extended The space Highlights • 10-minute walk to Siesta Key Beach • 3 Bedrooms / 2 Bathrooms • 2 Kings, Twin over Twin Bunks • Canal front house • Private heated Pool and Lounge Chairs • Outdoor Dining and BBQ Grill • Beach Chairs and Beach Cart • Washer and Dryer • Dog Friendly (with approval and fee) • 3 Parking Spaces Coastal Charm’s backyard is designed for relaxation, offering a sparkling private pool, plenty of lounge chairs, and a canal front backdrop. The covered outdoor dining area includes a BBQ grill, making it easy to enjoy breezy meals throughout your stay. Beach chairs and a beach cart are provided for convenient days at the shoreline, while the peaceful neighborhood setting enhances your long term comfort. Inside, the home features a warm and modern living room with a comfortable seating area and a TV for family movie nights. The fully equipped kitchen includes all the essentials needed for extended stays, along with ample storage and counter space. The dining area features a large table perfect for shared family meals. A washer and dryer are available for guest use, offering added convenience throughout your stay. The primary bedroom includes a King bed, walk-in closet, and ensuite bathroom with a walk-in shower. A second bedroom also features a King bed, providing plenty of comfort for multiple couples. The third bedroom is ideal for children with twin-over-twin bunk beds. All guests share access to a hallway bathroom with a walk-in shower. Room Details -Primary Bedroom: King bed, ensuite bathroom with walk-in shower -Second Bedroom: King bed -Third Bedroom: Twin over Twin Bunk Beds Located just a short walk from Siesta Key Beach and Siesta Key Village, this home offers convenient access to island dining, boutiques, coffee shops, and entertainment. Guests enjoy a peaceful canal front setting, private heated pool, outdoor dining, and space for up to 3 parked vehicles. The home is dog friendly with prior approval and fee. With its private pool, canal front setting, refreshed interiors, and excellent proximity to Siesta Key Beach and Village, Coastal Charm by Tropical Sands Accommodations is the ideal choice for extended island living. Book your stay today and enjoy the best of Siesta Key! Other things to note This home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Tropical Sands Accommodations Rental Policies for full details. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details. 3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Coastal Charm: Siesta Key Monthly Rental with Pool

🦩Exclusive Amenities Include: • Semi Private Heated Pool • 3 Minute Walk to Siesta Key Village • 1 Minute Walk to Siesta Key Beach • 3 Bedrooms, 2 Full Baths • 1 King Bed, 3 Queen Beds (Sleeps 8) • Screened in Balcony • Outdoor Dining Space • Free WiFi & 4 HDTV’s with Streaming Capabilities • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, & Kitchen Essentials • Gas Grill • Dog-Friendly with a Fee (1 dog up to 25 lbs, not quoted in price & charged after approval) The space 🌊 Sea La Vie | Steps to Beach + Shared Pool + Walk to Siesta Village  💖 Why You’ll Love This Home Stay just a heartbeat from the beach at Sea La Vie, a stylish duplex retreat offering island elegance, walkable charm, and a shared heated pool. Located just 1 minute from the shores of Siesta Key Beach and 3 minutes to the lively heart of Siesta Key Village, this side of the home is ideal for guests who want convenience, comfort, and a beachy atmosphere all in one.  👨‍👩‍👧 Perfect For Couples, families, or small groups who want their own private space but with shared access to outdoor amenities and close proximity to everything.  🌴 Live the Island Life Step inside and soak up the sunshine from your screened-in balcony, a perfect place to sip your morning coffee or unwind with a glass of wine. This unit is on the right side of the duplex and features a fully equipped kitchen, an open-concept living area, and 4 HDTVs with streaming to keep everyone entertained. Head upstairs to rest in any of the three inviting bedrooms, including a master suite with an ensuite bath.  Outside, take advantage of the semi-private heated pool, shared with Sea Esta, where loungers and tropical landscaping offer a resort-style experience. Fire up the gas grill for dinner, or head into the Village for seafood, cocktails, and live music—all just a few blocks away.  🛌 Where You’ll Sleep All bedrooms are on the second floor. Interior stairs required. • Bedroom 1: King Bed ·Shared Hall Bath · 2nd Floor, TV • Bedroom 2: Queen Bed · Shared Hall Bath · 2nd Floor, TV • Bedroom 3: Two Queen Beds ·Ensuite Bath· 2nd Floor, TV  📍 Prime Location • 0.1 Miles to Siesta Key Beach • 0.3 Miles to Siesta Key Village (Shops, Restaurants, Bars, Ice Cream) • Quiet Residential Street with Island Shuttle Nearby  ⏳ Availability Goes Fast Sea La Vie offers an unbeatable blend of location, charm, and amenities—just steps from both the beach and the buzz of the Village. Plus, it comes professionally cleaned through our CottageClean™ system for peace of mind.  📝 Need to Know: This is a duplex unit (right side of building). It shares the outdoor pool area and amenities with Sea Esta (left side), but all interior spaces are private. The pool is heated from November 15th – April 15th. All bedrooms are located upstairs and are accessible via interior stairs. Dog-friendly with fee (1 dog up to 25 lbs).

Sea la Vie | Walking Distance to Siesta Key Beach!

🦩 Exclusive Amenities Include: • Private Heated Pool • Water Front Home • Canal Access • 10 Minute Walk To Siesta Key Beach • Less than 1.5 miles from Siesta Key Village • 3 Bedrooms, 2 Baths • 2 King Beds, 2 Twin Beds, 2 Rollaway Beds (Sleeps 8) w/ linens provided • Outdoor Bar With Sink & Lounge Area • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided • Dog-Friendly with a Fee (1 dog up to 25 lbs, not quoted in price & charged after approval) The space 🌴 La Contento Casa | Private Heated Pool, Walk to Siesta Key Village and Beach  💖 Why You’ll Love This Home Awaken to sun-drenched mornings and tranquil canal views in this inviting waterfront retreat. La Contento Casa offers a seamless blend of indoor comfort and outdoor serenity, promising an escape where every moment feels like a breath of fresh air.  👨‍👩‍👧 Perfect For Families seeking a memorable beach vacation, couples desiring a peaceful waterfront escape, or small groups looking for a comfortable and convenient base to explore Siesta Key.  🎞️ Imagine This Your day begins with a gentle breeze drifting in as you relax on your covered back porch, watching the palms sway. After a leisurely breakfast prepared in the gourmet-grade kitchen with its convenient window pass-through to the patio, you gather your beach essentials—provided for your convenience—and take the short, invigorating 10-minute walk to Siesta Key Beach, feeling the world-famous white sands beneath your toes.  Back at La Contento Casa, the private heated pool is waiting, followed by an afternoon lounging by the water, perhaps with a drink crafted at your outdoor bar with sink. As evening approaches, the scent of a home-cooked meal fills the air, enjoyed alfresco with the canal views as your backdrop. Later, unwind in the spacious living area, sharing stories and laughter, before drifting off to sleep in one of the comfortable king beds, dreaming of another perfect day in paradise.  🛌 Where You’ll Sleep - Bedroom 1: King Bed, shared bath, main floor, TV  - Bedroom 2: King Bed, shared bath, main floor, TV  - Bedroom 3: Two Twin Beds, shared bath, main floor, TV  - Bonus Room: Two Rollaway Beds, located in common area  📍 Explore the Area Discover the best of Siesta Key with ease. 0.4 miles to Siesta Key Beach, renowned for its crystal-white quartz sand. Enjoy a delightful stroll or quick drive to Siesta Key Village (1.4 miles), offering an array of charming boutiques, diverse dining options, and vibrant coastal energy.  📝 Your Siesta Key Escape Awaits Don’t wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.  Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. This pool is heated between November 15 - April 15. Please note: There is 1 rental per 30 day period, per Sarasota, FL ordinance. Contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations.

La Contento Casa | Waterfront Home w/ Private Pool

The Oceanview 603 Oceanview 12-steps to Siesta Key’s best beach access! Stunning views with floor-to-ceiling “movable’ glass walls in master bedroom and living area. Just 3-min by trolley or bike to the Village. Remodeled in 2023. Free bikes and paddle boards. Communal lounging, alfresco dining, ping-pong, and Tiki bar. Perfect for families or couples wanting to relax, explore, repeat. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta The space What Guests Love ∙ Ocean Views – southwest views of Gulf and sunsets through floor-to-ceiling windows ∙ Gulf Breezes – wall of windows folds for unobstructed ocean breezes day or night ∙ Beaches – 12-steps to access of Americas top beach, white sand and calm clear water ∙ Relaxing – safe easy access to outside attractions and lots of plus-space on site ∙ Sunsets –walk 30-seconds to best sunsets or just enjoy from your living room ∙ Island Trolley –picks up out front, free of charge to all attractions and welcome’s drinks ∙ Activities – free bikes and paddleboards provided, scooter and golf cart rentals nearby  ∙ Extra Spaces –ping pong room, alfresco dining-lounging, DIY tiki bar in the back ∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch ∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts ∙ The Memories – walk to all Siesta Key's top attractions and guaranteed fun for all   The Beach Our beach access is across the street, 12-steps, and is quieter and more private. Although one of the most desirable on the Siesta Key and has no parking available so isn’t easy to access from rentals outside the neighborhood. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. A livelier beach scene with food, drinks and even a weekend drum circle is accessible a 5-to-10-minute walk south on the beach.   The Home Ocean view property contains just 3 units and was remodeled in 2022. Floor to ceiling glass walls in master bedroom and living area create wide-open southwestern exposures. Glass wall is bifold design and fully opens for maximum ocean or sunset views and refreshing breezes day and night. Common areas include the ping-pong room, tiki bar, alfresco dining, and usually cornhole. Set on the Southern edge of Siesta Village and surrounded by tropical plants. Just 10-second walk to top beaches, and 3-minute golf cart or trolly ride (10-minute walk) to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.   Bedroom Details This ocean view unit is 3BR and this unit is one staircase up from the ground. There is one large king bedroom, an ocean view queen bedroom, and a bunkroom with twin-over-full and twin-over-twin-bunks. Tempur-pedic rollaway beds are available with advance notice, and although the master bedroom is quite big, setting up by the window in the living room makes it the best sleeping area in the house. You can sleep up to 9 family style. Need more space? Ask about an additional unit nearby.   Beach Gear Provided We provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide "snorkeling gear" but this and anything you need can be rented or purchased nearby.   Household Items Provided We provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.   What to Bring It’s a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.   History – There’s no public parking in this area so, even though this is a gorgeous beach, it ends up being a little more private than most. When I was a kid growing up on Siesta Key, this beach access was called “Palm Island” and named after the island of the same name right at the end of the street. The island has a small bridge going to it and is literally a “heart shaped” island within the island of Siesta Key. When I was younger this was our lovers lane and, for me, it’s still the spot to fall in love or rekindle an old flame.    Post Booking Support We understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time.    Terms Payments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.   Travel Insurance If you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Gertrude's Siesta | Oceanview, 1-min to Beach

🦩Exclusive Amenities Included: • 3 Bedrooms, 2.5 Baths (Sleeps 8) • Free Parking • Living Room Fireplace • Fully Equipped Kitchen and Coffee Makers, Dishwasher • Beach Gear: Chairs, Towels, Cooler, Wagon Caddy • Partner Property Pool/Hot Tub Access • Access to Siesta Key Pickleball Courts • Starter Packs: Bathroom Toiletries & Kitchen Home Essentials • Enhanced Cleaning Protocols by CottageClean Team The space 🌴 Beachside Haven | Steps from Siesta Beach – Stunning 3-Bedroom Townhouse with Pool  💖 Why You’ll Love This Home Start your day with a stroll to Siesta Beach—just 0.1 miles from your front door—then wind down in the lanai or poolside. Nestled in an intimate, 4-unit complex with a heated pool, this townhome blends laid-back beach energy with stylish, multi-level living. It’s your slice of Siesta Key with unbeatable walkability and space to spread out.  👨‍👩‍👧 Perfect For Families, couples, and friend groups seeking beach proximity, shared indoor-outdoor spaces, and easy access to Siesta Key Village.  🎞️ Imagine This Wake to soft morning light pouring through vaulted ceilings. Head out for a beach walk—0.1 miles and you’re on Siesta’s sugar-white sands. After sun-soaked hours at the shore, retreat to your two-story townhome to cool off. Pour a drink and head to the pool for some relaxation or the shaded lanai. Fire up the grill for a feast or just relax in the comfy living room and catch up with a book or your favorite show. As the sun sets, take a 0.4-mile stroll to Siesta Key Village for dinner, music, and local charm.  🛌 Where You’ll Sleep Bedroom 1: King bed, ensuite bathroom, upper floor, TV Bedroom 2: King bed + workstation, shared hallway bath, upper floor, TV Bedroom 3: Queen bed, shared hallway bath, upper floor, TV Living Room: Queen sleeper sofa, half bath access, main floor Note: This is a 2-story townhouse. Stairs are required for all sleeping quarters.  📍 Explore the Area 0.1 miles to Siesta Beach 0.4 miles to Siesta Key Village 1.8 miles to Crescent Beach 7.5 miles to Downtown Sarasota (arts, dining, shops) Walk to restaurants, coffee shops, and ice cream spots You’ll love the walkability—bike or stroll to everything, or hop in the car to explore Sarasota’s world-class attractions.  📝 Don't Wait—This Home Books Fast Your reservation includes peace of mind with our CottageClean™ program, which features a 6-hour deep clean and 35-point inspection before every stay. Book now and walk into a home that feels freshly prepared just for you.  NEED TO KNOW: This home is a part of a small resort, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with other units. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. Contact us directly for more information regarding any shared space for this vacation property. Exterior cameras are present attached to the garage for security purposes only.

Beachside Haven Steps to the Beach with Pool

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories. The space Offering some of the best views of Siesta Key Dream’s portfolio and PRIVATE beach access with a gated key, this location features a crisp and airy 3 bed, 2 bath layout. This rental is perfect for family and friend gatherings and can accommodate up to 10 guests (8 adults and 2 children) with a total of 7 beds. This large, spacious floor plan connects a welcoming living room, a dining room that can accommodate well more than 8, and a full kitchen. Next to your living room, you’ll find a private, enclosed balcony with partial ocean views, comfortable seating that is perfect for shaded, outdoor entertainment. The deck is accessible through one the main bedroom as well, which shares similar partial ocean views. The third bedroom has three twin size mattresses, that include a third mattress that pulls out from the bottom, perfect for families with children! In addition there are two twin-sized roll-away-beds for the common area. Siesta Key Dreams is happy to provide free, high-speed internet & Wi-Fi, HD Televisions equipped with live sports & extension channel options via free streaming services, and electric appliances so you will not miss a beat. Outside on the top floor, you’ll have a shared rooftop sun deck and outdoor space that provides partial ocean and beach views. Siesta Keys Dreams provides lounge chairs and tables, perfect for tanning and hanging out in the Florida sun. Siesta Key Dreams always shows our exact address in our listings, so our guests know exactly how close they truly are to the beach and village. Unplug and explore your surroundings, such as the Siesta Village which is less than a 5-minute walk away down Beach road! From cafes to fine dining, local shopping and entertainment, you will certainly find what you need. If you’re looking to soak up the sun and clear waters, you will be given PRIVATE-access to the beach with a gated key, which provides you with a direct path to the beach access point within a mere 20 steps. Easily slip on your sandals and take a stroll on the private beach entrance point to experience the brilliant 99% white quartz sand. Looking for a larger space? Siesta Key Dreams can rent the entire building which includes the other condo in the building. Guest access The 3-bedroom 2-bath, and balcony are 100% private. The sundeck and ground floor patio are shared with the one other condo in the building. There are 2 parking spaces and reserved in the rear of the building. The access to the beach is gated, and guests will receive a special key to access the beach. The washer and dryer are dedicated to the unit and are in the lower lobby area of the building, next to the patio. Other things to note Siesta Key Dreams wishes to provide you with "Unreasonable Hospitality” – service at the highest caliber, well above your expectations. As soon as you secure your vacation rental, our team will provide you with clear expectations to help prepare for your stay. If you experience any issues upon arrival, a Guest Experience Manager who lives within the Siesta Keys area will be available at a moment’s notice to assist you. Siesta Key Dreams takes pride in providing professional and personalized services to ensure that your stay is unforgettable. Included within your reservation and rental cost are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & a Keurig-pods, and your choice of either a bottle of sparkling wine or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrella, blanket, cooler and a cart to transport your items easily! Traveling with your children? We offer complementary cribs, highchairs, toys, silverware, and baby-monitors available per request! Shortly after you secure your vacation rental, you will receive a link where you can book local services experiences provided by vendors throughout the island. Siesta Key Dreams provides golf-carts to rent and mid-stay services such as cleanings, and linen changes. When available, guests can request flexible booking with early check-in or late check out options. Siesta Key Dreams also offers baggage drop-off prior to your check-in time. You will be able to indicate your preferences in the link you will receive prior to check-in. Guests will receive a Rental Agreement via email that provides common details about our terms and conditions, such as our no-smoking policy. An electronic signature prior to the stay allows for us to provide contactless check-in and check-out!

Sundeck, 20ft to Beach Access, 500ft from Village

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories. The space Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories. The Siesta Key Dream’s flagship vacation rental features PRIVATE access to the beach via a gated private path, a lush and modern 3 bed, 2 bath layout, and a rooftop sundeck! This rental is perfect for family and friend gatherings and can accommodate up to 10 guests(8 adults and 2 children). This large, spacious floor plan connects a welcoming living room, a dining room that seats 8, and a modernized kitchen featuring stainless steel appliances. Next to your living room, you’ll find a private, enclosed balcony with comfortable seating that is perfect for shaded, outdoor entertainment and includes partial ocean views. Your Main Bedroom has partial ocean views, contains a luxurious king size bed and has direct access to the enclosed balcony. The second bedroom has a king bed and looks out towards Beach Blvd. In the third bedroom, you’ll find a bunkbed that has three-twin size mattresses(one pulls out from under the frame) and a queen sized futon, perfect for families with children! We also have a roll-away-twin-sized mattress/bed for the common area. We also have a roll-away-twin-sized mattress/bed for the common area. Outside on the roof-top, you’ll have a shared (with one other unit) sundeck and outdoor space that provides partial ocean and beach views – the best in Siesta Key Dream’s portfolio. Siesta Keys Dreams provides lounge chairs and tables, perfect for tanning and hanging out in the Florida sun. Our guests receive a beach-load-out, which includes beach towels, umbrella, chairs, blankets, and a cart. If you’re looking to soak up the sun and clear waters, pack-up the cart, walk 20-steps, use the PRIVATE access point (key provided) and you are now in the 99% white quartz sand. Want to get out of the sun, the enclosed balcony is a great choice or head downstairs to the front of the building, and hang-out on the front patio, fully shaded and great for people watching on Beach Road. Siesta Key Dreams is happy to provide free, high-speed internet & Wi-Fi, HD Televisions equipped with live sports & extension channel options via free streaming services, and electric appliances so you will not miss a beat. Siesta Key Dreams always shows our exact address in our listings, so our guests know exactly how close they truly are to the beach and village. Unplug and explore your surroundings, such as the Siesta Village which is less than a 5-minute walk away down Beach road! From cafes to fine dining, local shopping and entertainment, you will certainly find what you need. Looking for a larger space? Siesta Key Dreams can rent you the entire building which adds the second 3-bedroom condo. Guest access The 3-bedroom 2-bath, and balcony are 100% private. The sundeck and ground floor patio are shared with the one other condo in the building. The parking space is private and reserved in the rear of the building. The access to the beach is gated, and guests will receive a special key to access the beach. The washer and dryer are dedicated to the unit and are in the lower lobby area of the building, next to the patio. Other things to note Siesta Key Dreams wishes to provide you with "Unreasonable Hospitality” – service at the highest caliber, well above your expectations. As soon as you secure your vacation rental, our team will provide you with clear expectations to help prepare for your stay. If you experience any issues upon arrival, a Guest Experience Manager who lives within the Siesta Keys area will be available at a moment’s notice to assist you. Siesta Key Dreams takes pride in providing professional and personalized services to ensure that your stay is unforgettable. Included within your reservation and rental cost are complimentary bathroom toiletries (shampoo, conditioner, soap), coffee & a Keurig-pods, and your choice of either a bottle of sparkling wine or sparkling grape juice. To prep for the numerous beach trips, we provide you with towels, beach chairs, umbrella, blanket, cooler and a cart to transport your items easily! Traveling with your children? We offer complementary cribs, highchairs, toys, silverware, and baby-monitors available per request! Shortly after you secure your vacation rental, you will receive a link where you can book local services experiences provided by vendors throughout the island. Siesta Key Dreams provides golf-carts to rent and mid-stay services such as cleanings, and linen changes. When available, guests can request flexible booking with early check-in or late check out options. Siesta Key Dreams also offers baggage drop-off prior to your check-in time. You will be able to indicate your preferences in the link you will receive prior to check-in. Guests will receive a Rental Agreement via email that provides common details about our terms and conditions, such as our no-smoking policy. An electronic signature prior to the stay allows for us to provide contactless check-in and check-out!

Penthouse 20ft to Beach Access, 500ft from Village

Gertrude's Village House Top location on the island! Private gate into world famous Siesta Key Village! Three private patios. Skip the car and walk to white-sand cays, 20 bars and restaurants, quartz-sand beach, calm water, ice-cream, daiquiris, live music, craft beer, and fresh seafood. Sure to provide a combination of fun ease and relaxation you can't get in other vacations so book a special getaway now! - Tollbooth by AirbnbCorpMiddlemen, but this property is from GertrudeRentalsSiesta The space What Guests Love ∙ Beaches – 1-min walk to award-winning beaches ∙ The Village – 10 steps to private gate into world famous Siesta Village ∙ Relaxing – three private patios off bedrooms and living area ∙ Sunsets – 1-min walk to best sunsets in America & 300-degree Gulf views ∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch ∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts ∙ Activities - kayak, bike, paddleboard, scooter, golf cart rentals nearby  ∙ Island Trolleys - you're already where you want to be, but they’re fun:) ∙ The Memories - one of a kind Siesta Key experience, favorite of initiated visitors   The Beach Our beach is the widest, has panoramic views of the gulf to the North-West-and-South, and is the top spot in North America for sunsets. You can swim or wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin sand-dollars and “occasionally” manatee and giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. You can go from the water to lunch or dinner and back to the sand without putting on your shoes.   The Home You work hard, you deserve this. Three patios are 100% private and surrounded by tropical plants with shade umbrellas, chaise loungers and dining tables. Perfect for enjoying a quiet cup of coffee, good book, cocktail(s), or an al-fresco meal. It’s a few a steps off the patio to a private gate into the heart of the Village and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.   Bedroom Details This 3BR house is ground floor. Bedrooms include a king BR with French doors to a private patio, a queen suite with door to a private patio and bath, one bunk bed BR containing 2 twin over full beds, and a sofa in the living room. Need more space? We can get you a tempur-pedic rollaway bed or an additional unit nearby.   Beach Gear Provided We provide beach towels, chairs, carts, umbrellas, and usually have a few bikes and a paddleboard. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide "snorkeling gear" but this and anything you need can be rented or purchased nearby.   Household Items Provided We provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.   What to Bring It’s a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.   Post Booking Support We understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time.    History “Life is a string of pearls where you never know how many you have left.” - GVLJ. Gertrude Rentals was named for my grandmother “Gertrude” who traveled the world until age 91 but always insisted Siesta Key was the place she loved best. When I was young, she would take me to the beach and swim out so far, I couldn’t see her yellow flowered bathing cap even while standing on a chair! Today, you can laze float and wade in the same white quartz sand and calm crystal-clear gulf water she once did.    Terms Payments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.   Travel Insurance If you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Gertrude's Siesta | 1min to Beach Village Patio

Designer 3BR Siesta Key beach house with private dock and hot tub. Walk or bike to Siesta Key Village and Siesta Beach. This stylish Siesta Key vacation rental offers a peaceful setting and beautiful outdoor spaces perfect for relaxing under the palms. The space Tucked beneath the palms in the heart of Siesta Key, this thoughtfully designed 3-bedroom home offers the ease of a boutique stay with the privacy of your own retreat. Located just a short walk or bike ride to both Siesta Key Beach and Siesta Key Village, the home is perfectly positioned for days spent on the sand and evenings out at local restaurants and shops—no car required. Inside, the home is calm, layered, and intentionally designed—balancing comfort with a clean, elevated aesthetic. Each space flows effortlessly into the next, creating a relaxed environment that feels both refined and easy to live in. Bedroom Layout: Primary bedroom: King bed Bedroom 2: King bed Bedroom 3: Queen bed (Optional: add if you have pull-out/extra sleeping) The true highlight is the outdoor living experience. Step outside to a private tropical setting designed for slow mornings and long evenings: Private dock with water access for kayaking, fishing, or simply enjoying the view Hot tub tucked into a quiet, palm-lined corner Multiple lounging and dining areas for gathering or unwinding Additional amenities include: Fully equipped kitchen High-speed Wi-Fi Smart TVs Beach gear (chairs, umbrellas, etc.) Bikes for exploring the island Whether you're here for a family getaway, a long weekend, or an extended stay, this home is designed to make everything feel effortless—from how you start your mornings to how you end your day. Guest access Guests have full private access to the entire home and outdoor spaces during their stay. Main Floor: Open living area, fully equipped kitchen, and two king bedrooms with shared full bath. Upstairs Master Suite: Private retreat with balcony, kitchenette, and ensuite spa bath. Outdoor Spaces: Spacious deck, screened lanai, grill patio, hot tub, and private dock on the Grand Canal — perfect for fishing, kayaking, or simply relaxing by the water. The home includes keyless entry for easy self check-in, and parking for up to three vehicles in the driveway. You’ll enjoy the entire property to yourself — no shared spaces, no interruptions, just peaceful island living. Other things to note We’ve tried to think of everything to make your stay effortless and relaxing. The hot tub in the backyard is ready for you to unwind under the palms after a day in the sun. Guests can enjoy four beach cruisers, kayaks, and paddleboards — all included for exploring Siesta Key. The home sits on the Grand Canal, perfect for fishing or simply watching the boats drift by. Ritchie, our ever-helpful (and a bit cartoon-like!) maintenance guy, is nearby and always happy to lend a hand if anything comes up. Please note: This is a quiet residential area. We kindly ask that guests respect neighbors and observe quiet hours after 10 PM. Driveway parking available for up to three vehicles. This home was designed for relaxation — whether that’s morning coffee on the dock, sunset soaks in the hot tub, or lazy afternoons in the lanai.

The Shore House Private Dock Hot Tub

Welcome to Casa Force Majeure – Villa 2 Relax, recharge, and experience Sarasota from this stylish two-story home, perfectly located just 4 minutes from world-famous Siesta Key. Villa 2 offers three bedrooms, two bathrooms, and space for up to 9 guests, blending coastal charm with modern comfort. Nestled in a quiet bayfront neighborhood within walking distance to cafés, restaurants, parks, and sunset viewpoints, it’s a peaceful retreat that feels both connected and secluded. The space Wake up to gentle morning light, sip coffee on your private balcony, and plan a day exploring Sarasota’s beaches, shops, and waterfront cafés. Return home for dinner from the grill or a quiet movie night in the living room. Villa 2 offers its own entrance, driveway, and complete privacy. Guests needing additional space can book both villas together for up to 19 guests across the full two-home property. What Guests Love Most • Peaceful coastal setting near the beach yet away from crowds • Private two-story layout with bright interiors and new furnishings • Balcony with a two-person bistro table – perfect for morning coffee or sunset views • Walking distance to the bay, parks, and neighborhood restaurants • Fast 2 GB fiber Wi-Fi for streaming, remote work, or gaming • Fully equipped kitchen with everything needed for meals at home Property Highlights • 3 Bedrooms / 2 Bathrooms – Sleeps 9 • Private entrance and driveway (parking for up to 3 vehicles) • Fully equipped kitchen with stainless-steel appliances, Keurig, drip, and French press coffee makers, microwave, air fryer, rice cooker, toaster, and waffle maker, plus cookware, dishware, and food-storage containers • 65" Smart TV in the living room (bring your own streaming subscription) - no bedroom TVs, plus board games for all ages • Beach gear: 6 chairs, 2 umbrellas, 1 soft cooler, towels, and ice packs • Propane grill for outdoor cooking • Laundry room with starter supply of soap provided Sleeping Arrangements – Villa 2 • Bedroom 1: Queen + Bunk (Full + Twin) • Bedroom 2: Full • Bedroom 3: Full • 2 Full Bathrooms – one downstairs with tub/shower combo, one upstairs with shower • Dual-level access via indoor spiral staircase and exterior stairs to upper balcony doors (consider mobility needs or small children when booking) Outdoor Living Enjoy a peaceful private space surrounded by tropical greenery. Sip coffee or wine at the two-person bistro table on the upper-level balcony or use the propane grill for easy at-home meals. Outdoor seating is limited and best suited for couples or small-group relaxation. Newly Refreshed Comforts Villa 2 was recently updated with brand-new beds, linens, towels, cookware, dishware, and furnishings – the details that make a home feel crisp, clean, and cared for. Every space was thoughtfully designed for comfort and convenience, ideal for both short visits and extended stays. Distance to Local Favorites • Siesta Key Beach (ranked #1 in the U.S.) – 8 min • Crescent Beach – 6 min • Turtle Beach – 11 min • Lido Beach – 18 min • Nokomis Beach – 19 min *great for shark teeth hunting* • Venice Beach – 24 min • Downtown Sarasota – 11 min • Trader Joe’s / Publix / Target – under 10 min • Walgreens – 4 min | CVS – 6 min • Sarasota Memorial Hospital – 10 min • Urgent Care – multiple options nearby Explore Sarasota Like a Local • Morning walks to the bay or coffee at nearby cafés • Kayak or paddleboard rentals just minutes away • Explore boutique shops and art galleries downtown • Visit St. Armands Circle for dining and luxury shopping • Watch breathtaking sunsets from Bayfront Park or Siesta Key Beach • Take a day trip to Venice, Nokomis, or Anna Maria Island • Enjoy evening walks to the bay (one block) for beautiful sunset views over Siesta Key Comfort & Convenience • Keyless self check-in with unique code for each stay • Professional cleaning before every stay (plus optional mid-stay service for extended visits) • Starter supplies of K-cups, paper products, trash bags, dish soap, and laundry detergent • Beach towels and essentials provided • Toddler dishware included • Check-in 4 PM / Check-out 11 AM • Central A/C and heat throughout both levels • Driveway parking for up to 3 vehicles – no street parking hassle Work & Stay Ready Whether you’re working remotely or staying for the season, Villa 2 provides fast 2 GB fiber Wi-Fi and a quiet dedicated office area with desk and chair, ideal for virtual meetings or focused work. Safety & Peace of Mind • Exterior motion lights and exterior-only Ring camera in driveway • Smoke and CO₂ detectors throughout • Quiet hours 11 PM – 7 AM (outdoor noise only) Perfect For • Families or small groups • Extended stays and snowbird rentals • Remote work getaways • Beach vacations near Siesta Key Friendly Reminders • No pets • No parties or disruptive gatherings • Responsible events may be considered – please message first • No smoking on the property Your Sarasota Stay, Simplified Whether you’re here for Siesta Key beaches, Sarasota sunsets, or a quiet Florida getaway, Villa 2 offers a comfortable, private base for families and groups. Enjoy style, space, and convenience just minutes from the Gulf Coast’s most beloved destinations. Book your stay today and start planning your Sarasota escape. About the Property Layout Villa 2 is completely separate from Villa 1, with its own entrance, driveway, and living space. You will not share any indoor or outdoor areas with Villa 1 guests other than exterior trash and recycle bins. From Your Hosts We designed Villa 2 for comfort, connection, and relaxation. Our favorite evenings include food on the grill, dinner for two on the balcony under the stars, and quiet moments together after a day of exploring. This is our family’s vacation home, and we’re proud to share it with guests who will love it as much as we do. We care deeply about guest comfort and take great pride in our property. Guest access You’ll have full private access to the entire home and all outdoor amenities, including the grill, balcony seating, and private driveway. Entry is simple and secure with a smart keypad on the front door. A unique code is generated just for your stay and remains active only for your reservation – no keys to carry, share, or worry about losing. Come and go as you please, with the peace of mind that your stay is safe, private, and hassle-free. Other things to note • Traveling with little ones? We can recommend trusted baby-gear rental services that deliver cribs, highchairs, and strollers right to the home. • Pool access: the pool and pool deck belong to Villa 1 only and are not included with this listing. • Stairs: there is an indoor spiral staircase and an exterior staircase to the upper level. Please consider this if traveling with small children or anyone with mobility concerns. • Parking: private driveway fits up to 3 vehicles. • Security and privacy: exterior-only Ring camera in the driveway. Smart keypad entry with a unique code generated for your stay. • Quiet hours are 11 pm to 7 am. No parties, no pets, no smoking. • Work and stream ready: dedicated desk, 65" Smart TV in living room (no bedroom TVs), and ultra-fast 2GB fiber Wi-Fi. • Beach kit included: 6 chairs, umbrella, soft cooler, beach towels, and reusable ice packs. • Cleaning: home is professionally cleaned before every stay. Optional mid-stay cleaning is available for longer visits. • Starter supplies provided: K-cups, paper towels, toilet paper, trash bags, dishwasher pods, laundry pods, and dryer sheets. • Luggage drop-off and early check-in may be available on request, subject to availability. • Longer stays: ask about extended-stay guidance and potential monthly discounts. • Seasonal guidance: during hurricane season we follow county advisories. Trip insurance is recommended for added peace of mind. • Routine care: Florida homes receive regular landscaping and preventive pest service. Vendors do not enter the home without notice. • Trash and recycling days are posted in the house manual. • Local tip: Simon’s Coffee is just blocks away and is a favorite for great coffee and hearty food - perfect fuel before a long beach day. • Traveling with a larger group? Ask about booking both Villa 1 and Villa 2 together for up to 19 guests.

Bay View Retreat | 4 Min to Siesta Key | 9 Guests

Beautiful ocean front!!!! See the sunsets from our balcony on the Mermaid Penthouse Villa.. also just a 3 minute walk to the iconic Siesta Key Village and all it’s cool shops and restaurants! The space You will love staying in our mermaid villa as it is so close to all that Siesta Village has to offer. Obviously the best part is watching the beautiful Gulf of Mexico from your private balcony! Guest access Private garage if you would like to park your car there, private patio with ocean views. All amenities are included : Beach chairs, beach towels, Umbrellas.. Other things to note We do have access to an elevator however it is only for those who absolutely need it as it is a simple service elevator. Children are never allowed to use it and only those that absolutely absolutely can’t use the stairs please. We are pet friendly however only with prior approval at time of booking and additional non refundable pet fee of $100:)

Penthouse Oceanview Mermaid Villa

Beautiful coastal vibe three bedroom, dog-friendly home with private pool and outdoor living space. Walking or biking distance to the popular Siesta Key Village and gorgeous beaches. Gourmet kitchen with all the essentials. Large master suite with sunroom, private patio and outdoor shower. The space Experience the epitome of relaxation and coastal charm at our newly renovated Siesta Key vacation home. Nestled in a serene neighborhood, this stunning 3-bedroom, 2-bathroom retreat is a haven of tranquility, exuding a contemporary coastal vibe with its soothing light blue and white hues that perfectly complement the surrounding lush landscaping. With its thoughtful furnishings and impeccable design, this home promises to make your getaway truly unforgettable. Property Highlights -Open living area with French doors leading to a covered lanai -Wood-burning fireplace and flat-screen TV for cozy evenings -Saltwater pool with loungers, outdoor dining table, and extra seating Primary Bedroom -King bed, flat-screen TV, ensuite bathroom with spacious shower -Attached sunroom with desk, chair, private patio, and outdoor shower 2 Guest Bedrooms -Each with queen bed and flat-screen TV -Shared bathroom with shower/tub combo Queen Sleeper Sofa -Pull out sofa to accommodate extra guests Amenities -Beach gear provided -Fully fenced yard for privacy and pets -0.5 miles to Shell Beach -1 mile to public beach access & Siesta Key Village -10-minute drive to Downtown Sarasota for dining, shopping, and culture The Beauty of Siesta Key Siesta Key is a barrier island positioned between the Gulf of Mexico and intracoastal waterway. The powdery white sandy beaches are world renown and stretch over 8 miles along the southwest coast of Florida. Siesta Key is a water-lovers paradise offering crystal clear turquoise water, sailing, fishing, swimming and so much more. Play in the gentle waves and shallow waters, gather unique seashells, or build a sandcastle with your kids or grandkids. The Siesta Key Village offers a wide selection of shops, cafes, and live music for both its residents and guests. From local oyster bars to waterside dining, Siesta Key has something for every palate. Other things to note -A $250 pet fee, per pet is required. No dogs in the pool at any time. -A fee of $12 per day is charged for running the pool heater. If you wish to use the pool heater during your stay, kindly contact us to have it turned on. Thank you!

Saltwater Pool, Lanai, Office, 4 min to Siesta Key

Beautifully renovated ocean views Beautifully appointed with all amenities! Step out of this Tommy Bahama furnished villa and cross the street 100 yards to the ocean. Beach chairs, umbrellas are there for your use. The space Entire three bedroom two bath second-floor villa :-) Guest access Parking is available on property… Entire second story villa including patio is included Other things to note We are one block from the most desirable part of Siesta Key which is siesta key village! This coupled with direct access to the ocean makes for a quiet beautiful setting:) We are pet friendly however only with prior approval at time of booking and additional non refundable pet fee of $100:)

Mermaid Villa Gulf of Mexico Views

Welcome to paradise, be one of the very first guests to stay at our freshly remodeled waterfront home! Enjoy views of your very own backyard oasis, which features a saltwater pool, fire pit, covered lanai & grilling area, and private dock with direct access to the Gulf of Mexico. The home is conveniently located near the south Siesta Key Bridge making access to the key a breeze. Approximately 1.5 miles to Siesta Key beach by car or bicycle or skip the traffic and be on the water in minutes! The space Upon entering the home you will immediately notice the natural light pouring in through the large windows and sliders at the back of the house. Views of your backyard oasis can be seen from all of the common living areas and the home features an open concept with plenty of room for the whole family. The house can comfortably accommodate nine people. There was no detail overlooked in this home with all areas being freshly remodeled with new high quality furniture pieces and linens throughout! The primary bedroom features a king sized bed with private ensuite and access to the backyard. The home features a split floor plan, offering extra privacy for both you and your guests. The first guest bedroom features a king sized bed and the second guest bedroom has a queen sized bed as well as a bunk bed. The guest bathroom is easily accessible from both guest bedrooms. The backyard is truly a masterpiece, featuring an oversized travertine marble deck, saltwater pool with baja shelf for the kids, fire pit, covered outdoor grilling area, outdoor dinning area, tropical landscaping with green space, and 100ft of canal views with 40ft Azek dock. Bring your boat along, as this property offers a private dock with direct access to the Gulf of Mexico and the side yard offers fenced trailer and boat parking. You truly don't want to miss out on this property! Guest access Guests will have private access to the entire property. Other things to note If bringing a boat, please make sure you bring your own ropes and buoys to secure your vessel to the dock. The closest boat ramp to the property is the Turtle Beach Boat Ramp on Siesta Key. 30 night minimum.

Waterfront -Boat Access, 1.5m to Siesta Key Beach

Welcome to Siesta Bayside 3 Bedroom Condo! The space This stunning second-story, 3-bedroom townhome in Siesta Bayside combines luxury, comfort, and convenience. Just a 10-minute walk from Siesta Key Beach via private access, it’s located in a gated resort-style community with heated pools, a fitness center, BBQ area, and tennis/pickleball courts. A short stroll to the intracoastal offers a fishing dock, boat slips, and beautiful sunrise views. LOCATION HIGHLIGHTS: - Just a 5-minute drive to Siesta Key Village with dining, shopping, and nightlife - Nearby intracoastal bay access for fishing and boating - Free shuttle service available to explore the area without driving - Private beach access across the road - Two heated community pools, Tennis courts - Down the street from public beach PROPERTY FEATURES: - 3 Bedroom/ 2 bathroom townhouse condo (1495 sq ft) - Second-story unit accessible by stairs (no elevators) - Keyless entry and self check in - Dedicated WIFI and cable - Central A/C with ceiling fans - Parking in the driveway - Private washer and dryer - Can accommodate up to 8 guests, but no more than 6 adults max LIVING ROOM: - Comfortable seating area with access to the private balcony - Smart TV with cable and streaming capabilities - Private balcony with outdoor furniture KITCHEN AND DINING: - Updated kitchen with walnut cabinets, stone countertops, and stainless steel appliances - Plenty of cabinet and counter space - Two dining tables with plenty of seating - Seating for 4 at the breakfast bar BEDROOMS AND BATHROOMS: - Master bedroom (main floor): king bed , no cable but TV has streaming - Guest bedroom #1 (upstairs): king bed, smart TV with cable and streaming capabilities - Guest bedroom #2 (upstairs): two twin beds, smart TV with cable and streaming capabilities - Loft area (upstairs): daybed with trundle - Master ensuite bathroom (downstairs): large vanity room, walk-in shower - Guest bathroom (upstairs): spacious vanity with tub/shower combo EXTRA PERKS: - Complimentary beach items: a couple of beach chairs, a beach umbrella, and beach towels LOCAL FAVORITES: - South end: - Clayton’s Grill, Miguel’s, Captain Curt’s, Anna’s Deli, Orange Octopus, Crescent Beach Grocery - Village: Daquiri Deck, Siesta Key Oyster Bar, Another Broken Egg, Old Salty Dog, Siesta Market, Beach Club, Big Tiki Lounge IMPORTANT INFO: - Other than the beach access, no gulf side amenities (including their pool) are not available - Garage is accessed weekly by staff to remove garbage - Parking restrictions: no boats, motorcycle, trailers, jet skis, oversized or commercial vehicles allowed. - Golf carts are allowed but must be stored in the garage or driveway - Parking passes and onsite check in required THIS TOWNHOME IS IDEAL FOR A FAMILY BEACH GETAWAY: OFFERING COMFORT, STYLE, AND EASY ACCESS TO ALL THAT SIESTA KEY HAS TO OFFER. This property does not allow Emotional Support Animals in addition to their no pet policy. IMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions. Parking passes: 1 parking pass is provided. There is a fee for extra parking passes. Other things to note Please note that we may collect additional information from you after confirming your booking (usually an email address) in order to comply with local regulations and to provide the best possible experience.

Spacious Siesta Bayside 3BR: Private Beach & Lanai

Come enjoy a little slice of paradise in this 3 bed 2.5 bath home located just a few minutes walk (.4 miles) to Siesta Key Beach & Siesta Key Village! Enjoy the white sand and crystal clear waters of Siesta Key Beach, hanging by the pool, or exploring everything Sarasota has to offer! This place will not disappoint! The home offers a fully equipped kitchen, deck, pool, grill, fire pit and rec room w/ ping pong table. Convenient location in the heart of Siesta! The space Bedrooms equipped with king bed in master, two sets of twin bunk beds in middle room and 3rd room has a queen bed. From upstairs deck off living room, walk down steps to the pool/backyard and the fun room with pool table, lounging area and 1/2 bathroom. Pool towels are in the fun room in a cabinet. Guest access Pool Home is available; pet fee required for approved pet. $300. Other things to note This is a 3 bedroom and 2 and 1/2 bath home. The 1/2 bath is located in the downstairs fun room off the pool/backyard area. There is a gas grill, please clean as you use. And outdoor tiki torches to enjoy at night along with a fire pit.

Paradise In Siesta!

Welcome to this stunning second-level condo, Professionally managed by Gulf Coast Vacation Rentals, nestled within the prestigious Gulf and Bay Club Bayside in the serene enclave of Siesta Key. Boasting breathtaking views of the shimmering lake, this meticulously designed residence offers the epitome of luxurious coastal living. As you step inside, you are greeted by an inviting ambiance that seamlessly blends modern elegance with coastal charm. The spacious living area features an open floor The space Welcome to this stunning second-level condo, Professionally managed by Gulf Coast Vacation Rentals, nestled within the prestigious Gulf and Bay Club Bayside in the serene enclave of Siesta Key. Boasting breathtaking views of the shimmering lake, this meticulously designed residence offers the epitome of luxurious coastal living.  As you step inside, you are greeted by an inviting ambiance that seamlessly blends modern elegance with coastal charm. The spacious living area features an open floor plan, adorned with tasteful furnishings and large windows that bathe the space in natural light. Relax in the comfort of the living room, complete with plush seating and a TV, perfect for unwinding after a day of exploration.  Step outside to the private screened-in lanai and be mesmerized by the captivating vistas of the lake and lush greenery. Whether sipping your morning coffee or basking in the golden hues of the sunset, this outdoor oasis is the perfect spot to unwind and soak in the beauty of your surroundings.  The adjacent dining area offers a delightful space to enjoy meals with family and loved ones. The fully equipped kitchen is a culinary haven, featuring sleek countertops, stainless steel appliances, and ample cabinet space.  This condo boasts three generously sized bedrooms, each offering a tranquil retreat for rest and relaxation. The primary bedroom exudes comfort and sophistication, featuring a sumptuous king-size bed, with an attached bathroom. The second bedroom offers a queen-size bed, while the third bedroom is ideal for children, with two twin-size beds providing flexibility and comfort for all.  Guests of Gulf and Bay Club Bayside enjoy an array of upscale amenities, including beach access, tennis courts, swimming pools, fitness center, and lush tropical landscaping. With its coveted location in Siesta Key, renowned for its pristine beaches, vibrant dining scene, and eclectic boutiques, this condo offers the ultimate coastal lifestyle experience.  House Rules: No Motorcycles, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

2nd floor lake view condo on Siesta Key - GBB 1275

Family Fun at Surf's Up! This stylish Siesta Key home offers 2 living areas (adults & kids!), 2 king beds, and a private pool – all just steps to the USA's #1 beach! The space Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kids downstairs and a relaxing haven for adults upstairs. No need to fight over the king-size bed, as this home boasts two luxurious king-size bedrooms! Both offer comfortable retreats and easy access to your private pool, perfect for a refreshing dip anytime. The third bedroom features a trundle bed that comfortably sleeps two. Outside, the private pool area awaits with lounge chairs for sunbathing, an outdoor shower, and a delightful area to grill and enjoy alfresco dining at the table for six. Just moments away, the vibrant energy of Siesta Key Village, with its diverse culinary scene and local shops, offers endless opportunities for exploration. Surf's Up provides the ideal launchpad for experiencing all that Siesta Key has to offer, with plenty of room to relax and recharge in between adventures. Perfect for families seeking sun, relaxation, and easy access to Siesta Key Beach & Village. Book your unforgettable getaway now! Good to Know for Your Stay: • Property Management: This property is professionally managed by Ascendia Group, ensuring a seamless and enjoyable stay. • Beach Equipment: We want your beach days to be effortless! This property comes equipped with beach chairs, a cooler, a wagon, and beach towels for your enjoyment. • Pet Policy: We're delighted to welcome your furry family members! This property is pet-friendly, and a non-refundable pet fee (per pet) will be applied after booking and must be paid prior to check-in. Please feel free to inquire about the specific pet policy applicable to your reservation. • A Message from Ascendia Group: We're dedicated to ensuring your time at our property is relaxing, enjoyable, and full of unforgettable experiences. Our local team is always available 7 days a week during your stay if you have any questions or need recommendations on what to do and see in the area!

Renovated 3 bedroom-Walk to Beach & Village!

Imagine warm Florida sun on your skin, gentle Gulf waves whispering as you unwind in this spotless 3BR retreat minutes to Crescent Beach. Relax on the screened lanai with private, fenced HEATED pool—with door alarms for added safety. Perfect for families, beach-ready with chairs, buggy, umbrella, cooler & toys for effortless fun on powdery sands. Located in a quiet residential neighborhood. Get ready for adventure near Siesta Key’s vibrant charm: Siesta Beach, shopping, golf & aquarium! The space Screened in lanai with serene Pool- Fence, pool accessories and relaxing outdoor dining area! Beach chairs, buggy, coolers, wagon and stroller all located conveniently in large garage. Workspace area with high speed internet, desk and chair Laundry room with a washer, dryer and detergent Full kitchen - Fridge, Stove, Toaster/ Blender, Microwave and Dining area that seats up to 8. Two living spaces - one with 65” TV and one with cozy fireplace - both with entrances to pool and patio! Master room with King bed, ceiling fan, private bathroom with shower, shampoo/conditioner/soap and walk in closet. Room includes a private pool entrance. Guest room with Queen bed, closet, ceiling fan and personal vanity. Guest hallway closet equipped with additional linens, towels/ beach towels, pack and play with mattress and linens, chair height chair, baby bath, monitor and sound machine. Guest bunk room with two Queens and one Twin XL trundle. Guest bathroom with bath/shower and double vanity equipped with shampoo/conditioner and soap. Guest access Guests are free to use all areas of the home just not the locked cabinets. Other things to note Our home is located on a quiet family friendly residential street, please follow the quiet hours and absolutely no parties or additional guests other than originally listed or registered. A noise monitoring device is installed to help manage excessive volume, it measures sound levels only and does not record or transmit audio. No pets allowed

Casa Siesta: Heated Pool and walk to #1 Beach

🦩Exclusive Amenities Include: • Short Walk to Siesta Key Village & Beach • 3 Bedroom, 3 Full Bath • Rooftop Balcony • Two Balconies With Seating Areas • Private Garage & Gas Grill • Regular & Keurig Coffee Maker, Washer & Dryer, and Kitchen Essentials Provided • Beach Essentials Provided • Enhanced cleaning protocols provided by our CottageClean Team The space 🌴 Avanti Villa | Rooftop Deck, Walk to Siesta Key Beach & Village, Canal Access  💖 Why You’ll Love This Home Avanti Villa is a well-located Siesta Key retreat just a short walk to both Siesta Key Beach and Siesta Key Village. This three-bedroom duplex unit is designed for easy island living, combining walkability with comfortable indoor and outdoor spaces.The private rooftop deck creates a standout feature of the home, offering open views and a dedicated space to unwind throughout the day. Inside, the open-concept layout provides room to gather, while the elevator adds convenience across all levels. Located near the Grand Canal, the home includes access to a dock for kayaking, offering a simple way to get out on the water while still being close to the beach and village.  👨‍👩‍👧 Perfect For Families or small groups looking for a walkable Siesta Key stay, flexible sleeping arrangements, and access to both the beach and village.  🎞️ Imagine This Start your morning with a short walk to Siesta Key Beach, where the day begins with time on the sand and in the water. On the way back, stop in the village for coffee or breakfast before returning home to relax. Spend the afternoon enjoying time together in the open living space or head up to the rooftop deck for a quiet break. If you're looking to get out on the water, take advantage of the nearby canal access and launch a kayak from the dock. As evening sets in, walk to Siesta Key Village for dinner and live music, or stay in and gather on the rooftop as the sky changes color.  🛌 Where You’ll Sleep • Bedroom 1 – Second Floor: King Bed and Twin Daybed • Bedroom 2 – Third Floor: King Bed, Ensuite Bath • Bedroom 3 – Third Floor: Two Twin Beds • Common Area – First Floor: Queen Sleeper Sofa  📍Explore the Area • 0.6 Miles to Siesta Key Beach – Quick Walk to Sand and Gulf Waters • 0.5 Miles to Siesta Key Village – Dining, Shops, and Entertainment • 6.5 Miles to Downtown Sarasota – Bayfront Parks, Arts, and Restaurants • Nearby Grand Canal Access – Launch a Kayak from the Dock  ⌛Don’t Wait Your reservation includes peace of mind with our CottageClean™ program, featuring a six-hour deep clean and a detailed 35-point inspection prior to arrival.  🔎 Need to Know This home is part of a duplex and may share a dividing wall, floor, ceiling, or exterior areas with another unit. Guests will have access to a private backyard area and the left side of the building. Please contact us if you have any questions about the layout. Starter packs of kitchen and toiletry essentials are provided for your first couple of nights. Free high-speed WiFi is included. This home is equipped with an elevator for convenience.

Avanti Villa Walk to Beach & Canal Access

Terms Payments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location. The space What Guests Love ∙ Ocean Views – southwesterly ocean views from the balcony ∙ Beaches – 1-min walk to award winning Siesta Key beaches ∙ Relaxing – private balcony and patio with dining and lounging ∙ Pool – beautiful heated pool (shared) with tropical plants just 20 steps away ∙ Sunsets –walk 1-min to Siesta Key sunsets or just enjoy from the balcony ∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch ∙ The Fun - nearby Siesta Village has live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts ∙ Activities – bikes, paddleboards, scooter and golf cart rentals nearby  ∙ Island Trolleys –just 1-min walk to pick up, free of charge to all top attractions ∙ The Memories – walk to all Siesta Key is top attractions and guaranteed fun for all ∙ Price - this vacation rental listing is direct with the manager and is the guaranteed lowest cost  The Beach Our beach has a quieter Siesta Key Beach in front and to the right plus a lively popular crowd at the Public Beach 50 yards south. It is a top spot on the island for sunsets and on Sundays the world-famous Siesta Key Drum Circle happens 100 yards down the beach. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.   The Home Large 3BR home fully remodeled in 2023. Beautiful décor and thoughtful amenities throughout. Out-door grilling and dining, indoor and outdoor lounging, perfect for bigger groups, surrounded by palms. Set on the Southern edge of Siesta Village. Just 1-minute walk to top beaches, and 3-minute golf cart or trolly ride (15-minute walk) to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.   Bedroom Details This ocean view property is three stories, living space on the second and third floor. There is one large king bedroom, two queen bedrooms, a queen sleeper in the living room, a trundle under one of the queen beds and two Tempur-pedic rollaway beds. You can sleep up to 11 family style. Need more space? We can get you a tempur-pedic rollaway bed or an additional unit nearby.   Property Truths The pool at this location is shared with just three other units. Your unit is unit A, the pool is located behind units C and D, and this is only 20 steps from your building. While shared pools are "the norm" on the island, especially this close to the beach, people used to less popular beach destinations could be caught by surprise. Our properties in Vermont and New Jersey commonly have private pools, but don't go there if you can go to Siesta Key.   Beach Gear Provided We provide beach towels, chairs, carts, and umbrellas. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide "snorkeling gear" but this and anything you need can be rented or purchased nearby.   Household Items Provided We provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.   What to Bring It’s a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.   Post Booking Support We understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time.    Terms Payments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.   Travel Insurance If you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Gertrude's Siesta, Oceanview Pool 1-2 min to Beach

This surprisingly spacious 1200sf beach bungalow has been completely renovated in February 2020 from floor to ceiling. You will enjoy 3 spacious bedrooms with a private Master suite, spacious updated eat in kitchen and large family room. The unit is unique with a private deck to relax on at night. Walking distance to private beach access as well as a newly renovated heated salt water Community pool (Shared) on the intercoastal with breath taking views. This is a one of a kind experience. The space Siesta Keys has been voted the number one beach in the United States and is a family friendly community.

Sea Club II Garden House

Island Sun by Siesta Key Luxury Rental Properties is a bright and inviting 3-bedroom, 2-bath Siesta Key vacation rental located directly across from Siesta Key Beach, just a 1-minute walk from the white sand. With a shared tropical pool, a fun game room, and a pet friendly setup, this elevated duplex retreat offers a relaxed coastal atmosphere perfect for families and small groups seeking effortless coastal living near island restaurants, Crescent Beach, and the Siesta Key Breeze Trolley. The space Highlights • 1-minute walk to Siesta Key Beach • 3 Bedrooms / 2 Bathrooms • 2 Kings, Full over Full Bunk and Twin Trundle • Shared pool with sun loungers • Dog friendly (with approval) • Game room with foosball and bar seating • Outdoor dining and BBQ grill • Washer and dryer in unit • 3 parking spaces Island Sun invites guests to enjoy a tropical outdoor oasis, complete with a sparkling shared pool surrounded by swaying palms and comfortable loungers perfect for slow island mornings. The covered dining area offers space to gather for meals, while the BBQ grill makes cookouts easy. Downstairs, the game room brings extra fun to your stay, featuring a foosball table, bar seating, and an additional fridge; an ideal hangout zone between beach trips. Upstairs, the open concept living area features plush sofas, a large TV, and cheerful coastal decor that creates an inviting place to unwind. Glass doors bring in natural light and lead to the outdoor deck. The kitchen is equipped with a refrigerator, stove, microwave, cookware, and dishes, along with both countertop seating and a dining table; perfect for shared meals after a day in the sun. The primary bedroom offers a relaxing escape with a king bed, TV, and beach styling. The second bedroom also features a king bed and TV, making it ideal for additional couples or adult guests. The bunk room includes a full over full bunk bed with a twin trundle and a TV, creating a great kids’ or teens’ space. The upstairs bathroom includes a walk-in shower, while the second bathroom offers a shower/tub combination, ideal for families. A washer and dryer are available for guest use. Room Details -Primary Bedroom: King bed, TV -Second Bedroom: King bed, TV -Third Bedroom: Full-over-Full bunk bed with Twin Trundle, TV This home includes access to a shared pool, outdoor dining, BBQ grill, sun loungers, an outdoor deck, a game room, and convenient parking for three vehicles. Located along Beach Road and steps from the Gulf, Island Sun is close to local dining, ice cream shops, island boutiques, Crescent Beach, and the Siesta Key Breeze Trolley. Making it easy to explore the best of Siesta Key without needing to drive. Guests needing more space can book the neighboring duplex, Siesta Sun, for a combined total of six bedrooms and five and a half bathrooms. Island Sun by Siesta Key Luxury Rental Properties is the perfect blend of comfort, fun, and unbeatable location. Whether you’re relaxing by the pool, enjoying the game room, or watching Gulf Coast sunsets nearby, this home sets the stage for an unforgettable island escape. Book your stay at Island Sun today and experience the best of Siesta Key! Guest access When you rent this home, you'll have access to Unit B in the home. You have a shared game room and pool area with Unit A in this duplex. Other things to note This property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. This property has an active Ring doorbell and additional video surveillance on the pool equipment only. With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details. 3 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

Across the Street from Siesta Key Beach!

3BR/2.5BA Deluxe unit for 6 guests Ground floor Fully stocked kitchen Dining room table seats 8 Living area separate from Kitchen – separated Master and Twin Bedroom King bed in Master Bedroom- private full bathroom Iron and ironing board Flat screen television in Master and Living Area New furnishings and décor Updated bathroom fixtures Freshly painted Private porch with seating area Parking free for 2 vehicles Photos are for reference only, for specific requests please contact the structure.

Apartment for 8 guests

Siesta Key Beach Residence: This must-see, rare, and beautiful home on Siesta Key offers a much sought after moder and contemporary design. This unit, located on the 1st floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 10 guests. This home is perfectly located 0.1 miles from beach access #11, offering quick access to the #1 rated Siesta Beach! Enjoy the breathtaking view from the incredible rooftop pool and relax knowing your vacation home awaits! The space Bedroom 1: King Bedroom 2: King Bedroom 3: Queen bunk Living room: Queen Sleeper Sofa Kitchen, Dining Area, Private Balcony, and a Shared Rooftop Pool. The Location: - 0.1 Miles to entrance of Public Beach Access #11 - 0.6 Miles to Siesta Key Village - 2.1 Miles to Crescent Village - 0.6 Miles to Pool Access - 0.1 Miles to local free trolley stop. Siesta Key has 13 beach access points and a free trolley system making all of Siesta Key easily accessible no matter where you are on the island! Other things to note - This property is stairs only; all guest must have the ability to climb stairs. - Check-in is located at our office off site of the property. The address will be shared with check-in instructions. - We only guarantee 1 parking space per rental unit. No garage parking. - This home is dog Friendly. An additional charge of $39 Per Dog, Per Night will be applied. All other pets are not permitted. Please speak with a member of our team to confirm breed and weight restrictions. - Security Authorization Hold taken upon check-in: $1,500. This hold is released upon inspection of unit after check-out or charged for damages found to the unit. - To book a beachside managed Property Between February 1st and April 15th, the booker must be 27 years old or older and be present for the entire duration of the stay. Outside of this time frame, the standard minimum age for this property applies. Added Amenities Included in Your Stay: - Free Wifi - Beach Chairs, Beach Towels, Beach Wagon, and Beach Cooler, - Partner Property Pool/Hot tub Access, - Complimentary Bicycles Rentals located at Partner Property, - 7-days a week, Beachside Management office is open for your convenience and guest needs with after-hours support!

Stunning 3 Bed/ 2.5 Bath with a Shared Rooftop

The Beachside Retreat you have been looking for

Recently renovated & steps to the beach. Luxurious Beachfront Villa on Siesta Key. Discover the ultimate beachside vacation at our exclusive villa located on the pristine sands of Siesta Key. With breathtaking views of the Gulf of Mexico, this villa offers a perfect blend of luxury, comfort, and convenience. Step out your door onto a private access to the soft, powdery sands of Siesta. Enjoy expansive living spaces with windows that flood the villa with natural light and stunning sunset views. The space Our Villa has three full-sized bedrooms. Each bedroom has a 45 inch or larger TV and Wi-Fi access. The Master has an exceptionally large master bathroom with a brand-new large Jacuzzi jetted tub for two. Guest access All guests have private access to the beach and parking for up to three vehicles. Other things to note **Gulf view+ steps from the beach with rare private access to the beach on Siesta Key** We have both a washer and dryer.

Siesta Sunset Villa

Welcome to one of the few single family homes available directly on the white sands of Siesta Key! This 3 bedroom 2.5 bathroom house has a 2 car garage and is just steps to the beach and Gulf of Mexico. Walk to the Siesta Key Village where you can enjoy all the restaurants, shops, bars and entertainment that Siesta Key has to offer. Come stay in paradise. Book Today! The space - Guest access - Other things to note -

Located Directly on World Famous Siesta Key Beach!

Siesta Key Beach Residence: This must-see, rare, and beautiful home on Siesta Key offers a much sought after modern and contemporary design. This unit, located on the 2nd floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 10 guests. This home is perfectly located 0.1 miles from beach access #11, offering quick access to the #1 rated Siesta Beach! Enjoy the breathtaking view from the incredible rooftop pool and relax knowing your vacation home awaits! The space *THIS PROPERTY IS STAIRS ONLY! ALL GUESTS MUST HAVE THE ABILITY TO CLIMB STAIRS. *No garage parking. Driveway parking only. Bedroom 1: King Bedroom 2: King Bedroom 3: Queen Bunk Living room: Queen Sleeper Sofa Other things to note Added Amenities Included in Your Stay: Complimentary Bicycles Rentals, One Complimentary Parking Space, Wifi, Beach Chairs, Beach Towels, Beach Wagon, Beach Cooler, Partner Property Pool/Hot tub Access, Access to Siesta Beach Pickleball Courts, Siesta Key Trolly - Free-Rides Around Siesta Key, A 7-day week, Beachside Management office for your convenience and guest needs! *Pets are allowed, dogs only. Our pet fee is $39 per day/ per pet. Restrictions may apply on weight and breed, please check when making reservation. *No elevator access, must be able to climb stairs. *Minimum Age to Book: 25 *To book a beachside managed Property Between February 1st and April 15th, the booker must be 27 years old or older. *Security authorization Hold taken upon check-in. Amount: $1,500

Lovely 3 Bed/ 2.5 Bath with a Shared Rooftop Pool!

Siesta Key at Sunset-Top Floor

Build or Renovate    Discover an exceptional waterfront opportunity in the coveted Siesta Isles neighborhood on Siesta Key. Situated on an oversized lot at the intersection of two canals, this property offers 118 feet of seawall, wide water views, and direct boating access to the Intracoastal Waterway and the Gulf of Mexico. Experience prime Grand Canal waterfront, featuring a private dock and boat/jet ski lift.    The existing 3BR/2BA 1960s home features a split-bedroom layout, water views from the main living areas and primary suite, a two-car garage, interior laundry, Italian tile flooring, and a spacious screened lanai overlooking the expansive backyard—providing excellent space for a future pool. Mature tropical landscaping and a canopied street enhance the property’s appeal.    Important: The home experienced water intrusion during Hurricane Helene (Sept 2024) and is being sold AS-IS. This is a prime opportunity for renovators, investors, or anyone looking to build a custom waterfront estate in one of Siesta Key’s  canal-front locations.    Ideally located minutes from Siesta Key Village’s dining and shopping, and the world-famous powder-white sands of Siesta Beach. Downtown Sarasota is only a 15-minute drive. No HOA     A rare oversized waterfront parcel on the Grand Canal—renovate, rebuild, and create your ideal Siesta Key retreat.

742 Edgemere Ln Siesta Key, Florida

$158,469

Annual Revenue

Investment Value Over Time