Windmere Short-Term Rental Regulations: A 2026 Guide For Airbnb Hosts

Do you own a place in Windermere and you're weighing whether to put it on Airbnb or Vrbo? Well, the good news is that Florida law leans your way here, and the Town of Windermere, a small municipality inside Orange County, has never adopted a short-term rental ordinance at all. No town permit, no registration, no local bed tax. Going through the town's entire codified code for this 2026 refresh, chapter by chapter, the phrases "short-term rental" and "vacation rental" don't appear once.

Now the catch, because there's one and it decides everything else. "Windermere" names two places: the incorporated town, and a much wider spread of 34786 addresses in unincorporated Orange County that share nothing but the postal name. The county's zoning chapter divides up "the county, not part of any municipality," so it stops dead at the town line. Inside that line, the town's Land Development Code governs and says nothing about nightly rentals. Outside it, the county bans single-family transient rental in every residential district but one.

So let's walk through what it takes to do this properly: which of those two governments your address answers to, the one town rule that stops a lot of people cold, the state licence you can't skip, the three layers of tax on every booking, how enforcement works once a neighbour complains, and who to call at each step.

What are Short-Term Rental (Airbnb, VRBO) Regulations in Windermere, Florida?

Two codes do all the work, and which one reaches you comes down to a boundary line rather than a mailing address.

Start with the town, since that's the narrower case. Windermere's Land Development Code sets out what residential land can be used for in section 2.02.03, and the list runs three items long: single-family residential and accessory dwelling units, public service, and a public elementary school.

"All others are prohibited," the code says.

Look for a hotel category, a motel category, or anything resembling tourist accommodation, though, and you won't find one in any district, including the commercial one. Windermere never wrote transient lodging into its zoning in either direction.

That silence cuts both ways, mind you. Nothing in the code authorises a short-term rental. Nothing in it forbids one either.

What fills the gap is state law. Under Fla. Stat. § 509.032(7)(b), a local government "may not prohibit vacation rentals or regulate the duration or frequency of rental of vacation rentals," and that preemption has been law since 2011. Only ordinances adopted on or before June 1, 2011 escape it.

Windermere has nothing on the subject from before that date or after it. So there's no grandfathered ban sitting quietly in the code either.

One town rule does bite, though, and it catches people who assumed the guest house was the easy money. Section 7.02.07(c) says an accessory dwelling unit "may not be sold independent of the principal structure, rented, or leased."

Read that last clause carefully, because it isn't a 30-night minimum and it isn't aimed at Airbnb.

Renting the guesthouse or the accessory apartment is off the table at any duration, to anyone, for any money. That language arrived with Ordinance No. 2016-01 and still stands in the current supplement.

Now cross the town line and the picture changes hard.

Orange County defines a short-term rental as a stay of 179 consecutive days or less, and a "transient rental, single-family dwelling" as renting a single-family home for fewer than 30 days. Its use table at section 38-77 then assigns each to specific districts.

The county's instruction for reading that table is blunt: "No primary use shall be permitted in a district unless the letter 'P' or the letter 'S' appears" in that cell. A blank cell is a prohibition.

Here's how the two rows that matter fall:

• Short-term rental, resort residential and resort villa, the row that also covers hotels, motels and timeshares, carries a P only in C-1, C-2, C-3, I-1A, I-1/I-5, I-2/I-3 and I-4. Commercial and industrial land, in other words.
• Single-family dwelling transient rental carries a P in exactly one district, R-3, the multiple-family dwelling district. Every single-family residential district, R-1AAAA down through R-1 and all the country-estate districts, sits blank.
• Accessory dwelling units draw their own prohibition. Section 38-1426(14) bars "transient rental or leasing (a period of thirty (30) days or less)" of an ADU outside R-3.

The county's Zoning Division states the same conclusion in plain English on its own page. It also adds the one exit route the table hides: short-term rental is allowed "in Planned Developments (PD) where short-term rental is expressly permitted."

That PD carve-out is where the Disney-adjacent vacation-home communities live. It gets granted development by development, so it isn't something a homeowner can apply for after the fact.

Starting a Short-Term Rental Business in Windermere

Since the whole answer turns on which side of that boundary you're on, step one isn't a form. It's finding out which government you answer to.

Pull your parcel on the Orange County Property Appraiser's records, look at the municipality field, then confirm the zoning district. A 34786 address, a Windermere postmark and a Windermere school zone tell you nothing useful.

If the parcel comes back as unincorporated Orange County in R-1AA, R-1A or R-CE, the nightly-rental plan is dead on that lot and no permit revives it. Do check this before you write an offer, not after.

Assuming the parcel is inside the town and you're able to move ahead, the business is still narrower than it first looks:

• The whole house is the only real product. With the accessory dwelling unit off limits, splitting a lot into a main house plus an income guesthouse doesn't work here.
• There's no local permit to buy certainty with. Plenty of cities will sell you a registration that settles the question, whereas Windermere hasn't created one, so your protection is the state preemption rather than a certificate on the wall.
• Deed restrictions are a separate layer. Windermere is thick with gated and covenanted subdivisions, and an HOA restriction on transient use is a private contract that state preemption does nothing about.
• Life-safety, noise and parking rules still reach you. Preemption covers bans and frequency caps only, so the town keeps its ordinary zoning, building and nuisance authority in full.

The town has never published an interpretation of how a nightly rental fits its residential use list. Given that, I'd put the question to the Town Clerk in writing before you furnish anything.

Think of it as cheap insurance. A dated email answer from the town costs nothing, and it's a far better thing to hold than an assumption when a neighbour complains in month three.

Short-Term Rental Licensing Requirement in Windermere

That written answer settles the zoning question. It doesn't get you a licence, though, and you'll still need three of them before the first guest arrives.

The first is the state one, and it's the only true short-term rental licence in this guide. Florida treats a whole-unit nightly rental as a public lodging establishment, so Fla. Stat. § 509.241 requires a licence from the DBPR Division of Hotels and Restaurants before you operate.

It comes in two flavours: Vacation Rental Dwelling and Vacation Rental Condo.

As of July 2026, the Division's lodging fee schedule prices a single unit at a $50 application fee plus $170 for a full year, or $90 for a half year. A $10 Hospitality Education Program fee rides on top in every case, and a two-to-25-unit licence runs $180 for the full year.

Renewal is annual on a staggered schedule. Don't forget the 30-day window for reporting an address change through your online account.

Whether you need the licence at all turns on a test the legislature rewrote recently.

Chapter 2025-113 (SB 606) took effect July 1, 2025. A rental is now transient once it's rented "more than three times in a calendar year for periods of less than 30 consecutive days."

The count runs in consecutive days rather than calendar months, and occupancy is presumed temporary unless a written lease says otherwise.

So three short bookings a year keeps you outside the licence. The fourth pulls you in.

The second licence is the town's local business tax receipt.

Windermere's schedule at section 8-34 taxes "hotels, motels, apartments, roominghouses, lodginghouses, guesthouses or boardinghouses" at $10.00 for each bedroom rented. It carries a state law reference to F.S. § 509.271, so the state lodging licence has to exist before the town issues anything.

Receipts go on sale July 1 and are due on or before September 30, expiring the following September 30.

Miss that date and a 10% penalty lands in October, then another 5% for each month after, capped at 25%. Operate with no receipt at all and the town adds a 25% penalty on the tax due.

Ignore the notice for 150 days, though, and you're exposed to civil action, court costs, attorney's fees and a further penalty of up to $250.

The third licence is Orange County's own business tax receipt, which reaches inside municipalities too. County Code § 25-53 requires one for any business "anywhere within the limits of the county."

The Tax Collector's new-receipt page names Windermere on its short list of cities where "a municipal receipt must be secured before applying for the county receipt." So the order is fixed: state licence, then town receipt, then county receipt.

The county rate for renting accommodations is $1.00 per room under § 25-93, and the Tax Collector won't issue until your Chapter 509 licence is in hand.

Required Documents for Windermere Short-Term Rentals

Three separate offices means three separate stacks of paper, and none of them will chase you for the piece that's missing.

• Your DBPR licence application, filed under the right classification. A detached house is a Vacation Rental Dwelling; a unit in a condominium or cooperative is a Vacation Rental Condo.
• Proof of that state licence, which both the Town Clerk and the Orange County Tax Collector want before issuing a business tax receipt.
• A Florida Department of Revenue sales tax registration. Anyone renting transient accommodations registers as a dealer, and DOR expects a return even in a month with no bookings.
• An Orange County Comptroller tourist development tax account, registered separately from the DOR one. Different tax, different government, different login.
• Your FEIN or Social Security number. Windermere can't issue a receipt without one under § 8-24(f).
• A sworn statement of the room count, filed with the Town Council on or before September 1 each year and stated as of August 1, because the town's tax is calculated per bedroom.
• Sunbiz registration and any fictitious-name filing, if you're operating through an LLC rather than in your own name.

Keep your booking records too, and keep them longer than feels necessary.

Orange County requires every dealer to "secure, maintain and keep for a period of three (3) years a complete record of rooms or other lodging leased or rented," open to the Comptroller on request. That obligation has teeth, since the Comptroller can go to circuit court if you refuse the inspection.

Windermere Short-Term Rental Taxes

Assuming you get through the licensing and are able to start taking bookings, there's still tax, and it stacks in three layers from three different governments.

Charge	Rate	Collected by
Florida state sales tax on transient rentals	6.0%	Florida Department of Revenue
Orange County discretionary sales surtax	0.5%	Florida Department of Revenue
Orange County tourist development tax	6.0%	Orange County Comptroller
Town of Windermere local business tax	$10.00 per bedroom rented, annual	Town of Windermere
Orange County local business tax	$1.00 per room, annual	Orange County Tax Collector

The first two ride on one DOR return. Florida applies its 6% state sales tax to rental charges for living or sleeping accommodations of six months or less.

Orange County's discretionary sales surtax adds 0.5% on top. That's a school capital outlay surtax, extended effective January 1, 2026 and now running to December 31, 2035, and it has no single-item cap on transient rentals, so it applies to the full rental charge.

The third layer is the one people forget, because it never touches the state.

Orange County levies its tourist development tax in stacked pieces under sections 25-136, 25-136.1 and 25-136.2, adding up to 6% on any rental of six months or less.

Florida's DR-15TDT rate table confirms both the rate and the routing. Orange is a self-administered county, so that 6% goes straight to the Orange County Comptroller rather than to DOR.

The code puts the duty on the "dealer," meaning whoever receives the money from the guest. Quarterly returns are allowed only where the previous quarter's tax came in under $25.

Add it up and a Windermere guest pays 12.5% on the stay. Keep in mind that neither business tax receipt is part of that figure: those are flat annual costs on you, not percentages on the booking.

Platform collection takes most of this off your plate, at least on one platform.

Airbnb's own occupancy tax page lists Florida Transient Rental Tax at 6%, the Florida Discretionary Sales Surtax, and "Orange County Tourist Development Tax: 6% of the listing price including any cleaning fee for reservations 182 nights and shorter." All three are collected and remitted automatically.

I couldn't find an equivalent Vrbo-owned page naming Orange County, though. So if you list anywhere other than Airbnb, do check that platform's tax settings against your own DOR and Comptroller accounts.

Getting it wrong doesn't cancel the liability. It moves it back to you.

One thing Windermere genuinely doesn't charge is a local bed tax. The town's Chapter 34 carries a 10% public service tax on electricity, gas and water plus a special assessment fund, and that's the whole of it.

Florida has no personal income tax either, so your rental profit meets a federal return and stops there.

Florida Wide Short-Term Rental Rules

That missing local bed tax fits a wider pattern, because Florida has kept more of this power for itself than most states do.

The centrepiece is the preemption already mentioned. Since 2011, no Florida city or county has been able to ban vacation rentals or regulate how long or how often they're booked, and only ordinances adopted on or before June 1, 2011 are grandfathered.

What survives is ordinary land-use authority. That's exactly why Orange County's zoning table holds up while an outright ban wouldn't, since a rule about which district a use belongs in isn't a duration or frequency rule. Our Florida statewide guide works through where that line falls.

What Florida still doesn't have, and this trips up anyone reading 2024-era coverage, is a statewide short-term rental registry.

A 2024 package would have created one, widened the preemption and pulled advertising platforms into the framework. HB 1537 was laid on the table on March 5, 2024, and its Senate companion SB 280 passed both chambers and was then vetoed on June 27, 2024.

Neither became law, and nothing equivalent has been refiled since. So the DBPR licence remains the only state-level registration in the picture.

The 2026 session added nothing here either. A water-safety package would have required vacation rental licensees within 150 feet of a pool or water body to install safety features and file a compliance certificate at licensure and renewal.

CS/CS/SB 658 passed the Senate 37 to 0 on February 19, 2026, then died in Messages in the House on March 13, 2026, with companion HB 79 dying in subcommittee the same day. Given how many Windermere properties sit on the Butler Chain of Lakes, watch out for a 2027 refile.

The one change that did land is the 2025 occupancy test, and it matters more than the failed bills. Counting in consecutive days, plus a presumption that occupancy is temporary absent a written lease, quietly pulls casual arrangements into "transient" and therefore into licensing.

So if you rent to a seasonal tenant on a handshake, get the lease in writing.

Neighbouring counties handle the rest of it differently. The Orange County guide and the Osceola County guide are the useful next reads once your search widens past the town line.

Does Windermere Strictly Enforce STR Rules?

Enforcement is where the two jurisdictions diverge again, and where the honest answer is less dramatic than you'd expect inside the town.

The town can't enforce a short-term rental ordinance it doesn't have. What it can enforce is everything around one: parking, noise, trash, property maintenance, the accessory dwelling unit rule, and zoning generally.

Windermere runs a citation program under Code § 2-103. An officer gives written notice and up to 30 days to correct, then issues a civil citation if nothing changes.

A repeat violation, or a serious threat to health and safety, skips that notice period entirely. Each day a violation continues counts as a separate civil infraction, and the maximum penalty for each one is capped at $500.

The published fine schedule itself is modest. Under section 2-107, a Class 1 violation runs $50 for a first offense, $100 for a second and $150 for a third. Section 2-106 makes every Land Development Code violation a Class 1 unless it's one of three listed parking or alcohol items.

The special magistrate route is the one to take seriously.

Under the Land Development Code's enforcement provisions, a magistrate may impose a fine of up to $250.00 per day for a first violation and up to $500.00 per day for a repeat violation.

That's not a one-time ticket. It accrues daily until you come into compliance, a certified copy of the order becomes a lien on the land, and after three months unpaid the town manager may authorise the town attorney to foreclose on it.

Hearings are reserved for the first Tuesday of each month at 6:30 pm, and they convene only if a formal agenda gets posted.

Practically, all of this is complaint-driven and always has been.

Windermere's Code Enforcement desk is staffed by one officer, Stephen Zygaj, with published office hours of Mondays, Wednesdays and Fridays from 8:00 am to 12:00 pm. Nobody is patrolling for Airbnb signs.

Be aware that the complaint itself now carries a name, though. Florida's CS/SB 60, in effect since July 1, 2021, bars code enforcement from opening an investigation on an anonymous complaint, and the complainant has to give their name and address unless the violation is an imminent threat.

That cuts both ways. It filters out drive-by grumbling, yet it also means the neighbour who does file has already decided to put their name to it.

Outside the town line, the calculus is completely different, because there the county has an actual prohibition to enforce. A single-family transient rental in an Orange County residential district is a zoning violation on day one, and no amount of tax compliance fixes that.

Paying the tourist development tax on an illegal rental gives you a well-documented illegal rental.

How to Start a Short-Term Rental Business in Windermere

Given all that, the order below matters more than it looks, because the early steps decide whether the later ones are worth paying for.

1. Confirm the jurisdiction first. Pull the parcel record, check whether it sits inside the Town of Windermere or unincorporated Orange County, then confirm the zoning district.
2. If you're in the county, read the use table before anything else. Single-family transient rental is permitted only in R-3, and short-term rental generally only in the commercial and industrial districts or a PD that expressly allows it.
3. Read the covenants. An HOA restriction on transient use is enforceable whatever the zoning says.
4. Rule out the guesthouse. Inside the town, an accessory dwelling unit may not be rented or leased at all, so don't build a plan around one.
5. Put the use question to the Town Clerk in writing and keep the reply.
6. Apply for the DBPR vacation rental licence. Budget $50 plus $170 for a full-year single-unit licence, plus the $10 education fee.
7. Register with the Florida Department of Revenue, then separately with the Orange County Comptroller. Two registrations, two filing calendars.
8. Get the town business tax receipt, then the county one, in that order. Remember that the county won't issue until the municipal receipt exists.
9. Set the operating basics before the first booking. Off-street parking that keeps cars off the road, house rules that respect quiet hours, and a local contact who can reach the property fast are what keep a complaint from ever being filed.
10. Diarize September 30. Both business tax receipts expire then, and penalties start compounding on October 1.

Who to Contact in Windermere about Short-Term Rental Regulations and Zoning?

Whichever step you get stuck on, six offices cover the whole path, and knowing which one owns your question saves an afternoon on hold.

The town: zoning, licensing and enforcement

Town of Windermere, 614 Main Street, Windermere, FL 34786. Main line 407-876-2563, fax 407-876-0103.

• Town Clerk: Dorothy Burkhalter, (407) 909-5323. The Clerk's office administers business licences and holds the ordinances, so the local business tax receipt goes through here.
• Development Services and Building: 407-876-2563 ext 5327 for planning and zoning inquiries. Building permits run through PDCS, LLC, 407-277-9795, 3361 Rouse Road Suite #210, Orlando, FL 32817, and engineering through Wade Trim, 813-882-4373.
• Code Enforcement: Officer Stephen Zygaj, (407) 909-5330, at 614 Main Street, Building 100, inside the Police Department. Office hours are Mondays, Wednesdays and Fridays, 8:00 am to 12:00 pm.

One practical note on the code itself. The town's Municode publication is current only through Ordinance No. 2025-03, enacted May 13, 2025, which is Supplement 17.

The town's own guidance is to email the Clerk and confirm nothing has changed since the posting date. For a subject the code is silent on, that confirmation is the whole point of the call.

Orange County: zoning, business tax and the bed tax

• Zoning Division: 407-836-3111, [email protected], 201 S. Rosalind Avenue, Orlando, FL 32801. Ask here which district a parcel sits in and whether a planned development expressly permits short-term rental.
• Tax Collector, Business Tax Department: 301 S. Rosalind Ave., Orlando, FL 32801, (407) 434-0312 option 2. Open Monday to Friday, 8:30 am to 5:00 pm, opening at 9:00 am on Wednesdays, last application accepted at 4:00 pm.
• Comptroller, Tourist Development Tax: P.O. Box 4958, Orlando, FL 32802-4958, phone 407-836-5715, fax 407-836-5626. Registration and monthly filing both run through the Comptroller's online system.

The state: licensing and sales tax

• DBPR Division of Hotels and Restaurants: 2601 Blair Stone Road, Tallahassee, FL 32399-1011, (850) 487-1395, [email protected]. This office issues and renews the vacation rental licence.
• Florida Department of Revenue: registration, returns and the 6% state sales tax plus the 0.5% county surtax run through floridarevenue.com.

What Do Airbnb Hosts in Windermere on Reddit and Bigger Pockets Think about Local Regulations?

Those phone numbers give you the official position. What operators say is a little different, and the gap between the two is itself informative. What follows is my read of the public discussion rather than any kind of survey, so do weigh it accordingly.

The dominant view among Central Florida investors is that Windermere is somewhere you live, not somewhere you run nightly rentals.

Orlando realtor Courtney Bass put it directly in a BiggerPockets thread on Orlando short-term rental strategy. "The Orlando short term rental market is centered in Kissimmee and Davenport areas and many communities are set up for this and allow it," she wrote, while "as you edge in to dr. Phillips, Windermere and Orlando in general, it is not permitted, though some people get away with it as Airbnb." Her recommendation was to buy something already zoned for it.

That comment dates from 2018, so treat it as an operator's read on where the business sits rather than a current statement of law. It does line up with what the county's use table says today.

Two themes recur beyond that.

The first is confusion over exactly the boundary problem this guide opens with. People describe buying "in Windermere" and discovering their parcel answers to the county, or the reverse.

The second is that HOA covenants, not city hall, are what stop most Windermere-area hosts. That matches the legal structure, since Florida's preemption constrains governments and does nothing at all to a private restriction recorded against your deed.

Nobody credible argues that the county's zoning position is unclear. What people argue about is whether it gets enforced in any given subdivision, which is a different question and a much worse one to bet a purchase on.

Weighing this against places in the state where whole-home rentals are squarely permitted? The Florida market data is worth comparing side by side first. Then run the specific address through BNBCalc to see how the numbers land once the tax stack is in.

Boundaries like this one deserve more attention than the rulebook itself, because a code you've read carefully tells you nothing if it governs the street rather than your lot. Wherever you end up buying, find out which government owns your parcel before you find out what it allows.

Frequently Asked Questions

Can you legally run an Airbnb in Windermere, Florida in 2026?

Inside the incorporated Town of Windermere, yes. The town has no short-term rental ordinance, no registration requirement and no local bed tax, and Florida law bars a local government from banning vacation rentals outright. You'll still need a state DBPR vacation rental licence plus town and county business tax receipts. Outside the town limits, in unincorporated Orange County, renting a single-family home for fewer than 30 days is permitted only in the R-3 district.

Does Windermere require a short-term rental permit or registration?

No. The Town of Windermere's Code of Ordinances and Land Development Code, codified through Ordinance No. 2025-03 enacted May 13, 2025, contain no short-term rental or vacation rental provisions at all. What the town does require is a local business tax receipt at $10.00 per bedroom rented, issued only after the state lodging licence is in hand, and due on or before September 30 each year.

What taxes do you pay on a Windermere short-term rental?

Three layers apply to every booking of six months or less: 6% Florida state sales tax, a 0.5% Orange County discretionary sales surtax, and a 6% Orange County tourist development tax, which comes to 12.5%. The first two go to the Florida Department of Revenue and the third goes directly to the Orange County Comptroller. Airbnb collects and remits all three automatically. Annual business tax receipts from the town and county are separate flat costs.

Can you rent out a guest house or ADU in Windermere on Airbnb?

No, and the restriction is broader than short-term rental. Land Development Code section 7.02.07(c) says an accessory dwelling unit "may not be sold independent of the principal structure, rented, or leased," so a Windermere guesthouse or accessory apartment cannot be let at any duration. Orange County applies a narrower version outside the town, prohibiting transient rental of an accessory dwelling unit for 30 days or less except in the R-3 district.

What are the penalties for an illegal short-term rental near Windermere?

Inside the town, code citations run $50, $100 and $150 for first, second and third offenses, with each day counted as a separate infraction and a $500 cap per violation. A special magistrate can go further, imposing up to $250 per day for a first violation and $500 per day for a repeat, then recording the order as a lien on the land. In unincorporated Orange County, a residential-district transient rental is a zoning violation from day one.

Last verified: July 2026. Every ordinance, tax rate, state law, and contact detail in this guide links to or comes from its official source.