Thinking about listing your Winter Park place on a nightly site? The rules here are stricter than many nearby areas, and a mistake can get expensive. You want clear answers before you buy, list, or invest. In this guide, you will learn what Winter Park allows, how state licensing and local taxes work, and a simple checklist to verify any address. Let’s dive in.
Winter Park’s base rule
The City of Winter Park states that the “rental, use or occupancy of any residential dwelling for less than one month shall be prohibited.” If you own a single‑family home in a residential zone, you cannot legally rent it for fewer than 30 days. That is the starting point for most properties inside city limits. You can review the city’s guidance on its Safety and Code Compliance page for confirmation and context. City of Winter Park Safety & Code Compliance
What this means day to day
- Nightly or weekend stays in a typical single‑family home are not allowed.
- Month‑to‑month or 30‑day‑plus leases are the standard path for residential properties.
- If a property is not in a residential zone, different use rules can apply. Always verify the zoning and permitted uses for the specific address. Winter Park Code of Ordinances
Check zoning first
Permissibility can change based on zoning and building type. Before you plan any rental activity, confirm the property’s zoning and whether a business can operate at that address. The city’s Planning and Zoning team and Business Certificate page are the best starting points. Business Certificate and Zoning Contact
Condos, multifamily, and HOAs
Condo and multifamily buildings layer in extra rules. Even if state licensing would allow a vacation rental, the condo association or HOA may prohibit it. Always review the association’s covenants and bylaws, and get written confirmation if you plan to rent. Hosted stays in an owner‑occupied unit may be treated differently by state licensing, but local rules and association rules still apply. DBPR vacation rental guidance
State licensing and preemption basics
Florida’s Department of Business and Professional Regulation, through the Division of Hotels and Restaurants, licenses vacation rentals. A license is required when a dwelling is rented more than three times in a year for periods of less than 30 days, or if you market it as regularly rented. Entire‑unit rentals fall under the Vacation Rental license categories. You can review requirements and search licensed properties in the state database. DBPR vacation rental guidance
Florida law also includes a preemption provision in Section 509.032 that limits what new local vacation‑rental rules can do, with certain older ordinances grandfathered. This is why the details can be nuanced and property specific. Lawmakers debated major changes in 2024, but SB 280 was vetoed, and future sessions may revisit the topic. Always verify the current status before acting. Florida Statutes §509.032 | SB 280 (2024) history
Taxes on short stays in Orange County
Short‑term or transient stays are subject to state and county taxes. Florida imposes sales tax on transient rentals, and Orange County adds a 6 percent Tourist Development Tax. The combined rate on a short stay is often around 12.5 percent when you include the state rate, local surtax, and county bed tax, but totals vary by property and platform agreements. Confirm who collects and remits the taxes before you host. Florida transient rental tax statute | Orange County Tourist Development Tax
Local operations and enforcement
If you operate any rental business inside city limits, the city may require a Business Certificate and zoning confirmation. The city also enforces parking, quiet hours, trash handling, and nuisance rules that affect renters and guests. Operating in violation of the code can lead to investigations, fines, and corrective orders. If you are unsure, contact Safety and Code Compliance before you list. Business Certificate and Zoning Contact | Safety & Code Compliance
Step‑by‑step compliance checklist
Confirm the address is inside Winter Park city limits, not unincorporated Orange County. Business Certificate and Zoning Contact
Verify zoning and permitted uses for the parcel. Residential zones in Winter Park prohibit rentals under one month. Safety & Code Compliance
Review HOA or condo bylaws. Get written approval if required.
If you plan stays under 30 days, review DBPR licensing and obtain the appropriate vacation‑rental license if eligible. DBPR vacation rental guidance
Obtain any required Winter Park Business Certificate and set up state and county tax accounts, including Orange County’s Tourist Development Tax if applicable. Business Certificate and Zoning Contact
Post house rules for parking, quiet hours, and trash. Maintain a local contact who can respond quickly to complaints. Safety & Code Compliance
Meet safety standards such as smoke detectors and egress. Some buildings require additional inspections under DBPR rules. DBPR vacation rental guidance
To verify a listing’s status, search the DBPR database and contact the city for local authorization questions. DBPR Division homepage
Buyers and sellers: what it means
If you are buying with an STR strategy, plan for 30‑day‑plus rentals unless your property type and zoning clearly allow something different. Build HOA rules, city permissions, DBPR licensing, and tax accounts into your due diligence timeline. If you are selling, set expectations about rental potential and market accordingly, such as positioning the home for medium‑term furnished stays.
Ready to talk through a property’s zoning, rental potential, and next steps for Winter Park or nearby markets? Reach out to the Central Florida RE Team for local guidance and a plan that fits your goals.
FAQs
Are short‑term rentals allowed in Winter Park single‑family homes?
- Winter Park states that renting a residential dwelling for less than one month is prohibited, so nightly or weekend stays in typical single‑family zones are not allowed. Safety & Code Compliance
Do Winter Park condos follow different rules for short stays?
- Condos are subject to state vacation‑rental licensing for entire‑unit rentals and to the condo association’s bylaws, which may prohibit or limit short‑term rentals, so confirm both before you list. DBPR vacation rental guidance
What license is required for a Florida vacation rental unit?
- DBPR requires a vacation‑rental license when a dwelling is rented more than three times in a year for periods under 30 days, or if it is marketed as regularly rented. DBPR vacation rental guidance
What taxes apply to short stays in Orange County, Florida?
- Expect state sales tax on transient rentals plus a 6 percent Orange County Tourist Development Tax, with total short‑stay taxes often around 12.5 percent depending on the property and any platform collection. Florida transient rental tax statute | Orange County TDT
How can I check if a Winter Park listing is legal?
- Search the DBPR Vacation Rental Database for a license, contact Winter Park Planning and Zoning about local authorization, and review any HOA or condo rules that control rentals. DBPR Division homepage
