Short answer: in most of the city, no. Winter Garden blocks short-term rentals in most residential zones. The main exception is an owner renting out part of a home they live in. That one fact changes the math on a lot of investment properties here, so it pays to know it before you write an offer.
Winter Garden sits in Orange County. Among local investors, it has a reputation as one of the stricter short-term rental markets in Central Florida. Kissimmee and parts of Davenport welcome nightly rentals with far fewer hurdles. Winter Garden does not. Here is what the city actually requires, what it costs, and where an Airbnb might still work.
What counts as a short-term rental in Winter Garden?
Any home, or part of a home, rented for less than 30 days counts as a short-term rental here. That matches the statewide definition in Florida law. Two things trigger a state license. One: you rent a whole home more than three times a year for stays under 30 days. Two: you advertise it publicly as a vacation rental. Either one means you need a license from the Florida Department of Business and Professional Regulation under Florida Statute Chapter 509.
Renting a single room in a home you live in works differently. The state does not count that as a lodging establishment, so it skips the DBPR license. A whole-home nightly rental does not get that break.
Where does the city actually allow short-term rentals?
Winter Garden limits short-term rentals to specific zoning districts. Most standard residential neighborhoods are off-limits, according to the city's Planning and Zoning Division (current as of 2026, via cwgdn.com). The main path that still works is an owner renting out part of a home they occupy. Buying a house purely to run it as a full-time nightly rental in a typical Winter Garden subdivision fights the zoning code from day one.
Check the zoning district before you make an offer on any rental property. Call the Planning and Zoning Division directly and ask. Local investors say the city actually enforces these rules. It is not just a rule on paper. Skip this step and you risk fines and a denied license, even if no neighbor ever complains.
What does it take to get licensed?
If your property qualifies, start with a Land Use Review Application through the Planning and Zoning Department. That review usually takes 5 to 10 business days. It confirms your property sits in an allowed zoning district. This timeline comes from the city's published process as of 2024 (BNBCalc). Confirm the current timeline with the city directly.
Once that clears, you need two things from the city: a Local Business Tax Receipt and a Short-Term Vacation Rental License. The tax receipt costs $100. The rental license costs $300 a year. Renew it by September 30 to avoid late fees. Every unit needs its own license. One application cannot cover a duplex or multiple addresses.
The license application asks for several documents. You need a notarized form and proof of the state DBPR license. You also need active tax registrations with the Florida Department of Revenue and Orange County Tax Collector. On top of that: liability insurance, a property sketch showing exits and parking, and proof of smoke detectors and fire extinguishers. If a condo or homeowners association covers the property, you need its written consent too. An HOA ban on short-term rentals overrides everything else. The city will not issue a license if the association says no.
Winter Garden Short-Term Rental Costs, At a Glance
| $100 | Local Business Tax Receipt, required for any short-term rental operation. City of Winter Garden Planning and Zoning Division, current as of 2026 |
| $300/yr | Short-Term Vacation Rental License fee, renewed by September 30 each year. City of Winter Garden Planning and Zoning Division, current as of 2026 |
| 12.5% | Combined tax on rental income: 6% Florida transient rental tax, 0.5% Orange County discretionary surtax, and 6% Orange County Tourist Development Tax. Florida Department of Revenue and Orange County Tax Collector, current as of 2026 |
| 5-10 days | Typical turnaround for the city's Land Use Review Application before licensing can begin. City of Winter Garden Planning and Zoning Division, current as of 2026 |
What are the taxes on a licensed Winter Garden rental?
A licensed short-term rental here owes 12.5 percent combined tax on the rental charge, including cleaning fees. Three taxes make up that total. A 6 percent Florida transient rental tax. A 0.5 percent Orange County discretionary sales surtax. A 6 percent Orange County Tourist Development Tax. You collect this from the guest. Then you send it to the Florida Department of Revenue and the Orange County Tax Collector, usually every month.
Two groups can skip the transient rental tax if they have the right paperwork. One is full-time college students. The other is active-duty military on official orders. Most vacation guests do not qualify.
Weighing a rental property in Winter Garden?
Zoning and licensing rules can make or break the numbers. Talk to a local agent before you write an offer.
Is Winter Garden a good market for short-term rental investment?
For a licensed, owner-occupied setup, it can work well. For a pure investment play built on nightly income alone, Winter Garden fights you harder than its neighbors do. The zoning rule against non-owner-occupied whole-home rentals rules out the exact setup most STR investors want. That is a standalone house, never lived in by the owner, rented out every week of the year.
Investors chasing nightly rental income tend to look toward markets built for that model instead. Kissimmee's short-term rental rules allow the practice far more broadly. That is part of why so much vacation-rental investment has landed near the theme park corridor instead. If cash flow from nightly guests is the real goal, a market with fewer zoning restrictions gets you there faster.
That does not make Winter Garden a bad place to buy. It makes it a market where your return comes from home value growth and steady long-term tenants, not nightly turnover. Want new construction with fewer zoning headaches? Some investors look just outside city limits, toward communities like Mirabella in Davenport.
Buyers who already plan to live in Winter Garden full time have an easier path. Renting a spare room or an attached suite while you live in the home still qualifies under the owner-occupied exception, once you clear licensing. That gives you rental income without fighting the zoning code. Browsing current homes for sale in Winter Garden with a guest suite or in-law layout is a good starting point if this setup interests you. It just will not replace a full-time vacation rental business.
How the Erica Diaz Team can help
A zoning question like this one can decide whether a deal works before you ever negotiate price. As a Winter Garden real estate agent team, we have handled short-term rental purchases across Central Florida. That experience tells us which Winter Garden neighborhoods still have a real path to a rental license. It also tells us which ones do not. That is the kind of detail worth getting right before closing, not after.
Maybe you already own a Winter Garden property and want to rent it short-term. Maybe you are shopping for one with that goal in mind. Either way, a quick conversation with the team before you apply for anything with the city can save you weeks and application fees.
Not sure if your property qualifies?
We'll help you check the zoning before you spend a dollar on licensing.
Zoning, licensing, and tax figures in this post reflect Winter Garden's published requirements as of 2026, sourced from the City of Winter Garden Planning and Zoning Division, the Florida Department of Business and Professional Regulation, and the Florida Department of Revenue. Local ordinances change. Confirm current rules directly with the City of Winter Garden Planning and Zoning Division at 407-656-4111 before making a purchase or licensing decision. This post is informational and is not legal or tax advice.
