Overview: Are STRs allowed in Winter Park, FL? (explicit answer)

• No. Short-term rentals are prohibited in Winter Park. City code Section 58-71(aa) states that “the rental, use or occupancy of any residential dwelling for less than one month shall be prohibited.” [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]
• The ordinance applies to any residential dwelling unit. There is no carve-out in the ordinance for hosted rentals (e.g., renting a spare bedroom) or for “minimum stays” shorter than one month; even hosted arrangements must comply with the prohibition if they involve stays under one month.
• City enforcement has been active. Multiple community reports from Airbnb hosts describe notices and escalating enforcement actions (including Board hearings and daily fines) when operating rentals of less than 30 days. [Source: Airbnb Community Thread] [Link: community.withairbnb.com/t5/Help-with-your-business/Short-term-rentals-in-Winter-Park-FL/m-p/1379104]
• Practically, the only compliant form of rental for investors in Winter Park’s residential areas is long‑term tenancy of 30 days or more. If you wish to pursue short-stay products, you must first verify whether any nonconforming (“grandfathered”) rights or zoning exceptions exist for your specific property; absent that, any listing under one month will be treated as a violation.

Note on conflicting third‑party claims: A blog post suggests STRs may be allowed in certain commercial zones with a Business Tax Receipt. That conflicts directly with the city ordinance quoted above. Treat such claims cautiously and confirm with the city before relying on them. [Source: Ross Janke Real Estate Blog] [Link: rossjankerealestate.com/blog/winter-park-fl-short-term-rental-rules-what-investors-need-to-know]

How to start a rental business in this market (given Winter Park’s STR prohibition)

• Step 1: Decide your strategy
  • Long‑term rentals (≥30 days): The only clearly compliant pathway in residential zones. This approach avoids STR licensing and stays fully within the Land Development Code.
  • Short‑term rentals: Only pursue if you can verify a lawful pathway, such as:
    • A legally recognized nonconforming/grandfathered use on the specific parcel; or
    • Zoning that expressly authorizes transient rentals (you must obtain written confirmation from Planning & Zoning).
• Step 2: Zoning diligence
  • Confirm the property’s zoning district and whether any prior approvals allow short‑term stays. If you cannot produce a city‑issued determination allowing STRs, assume STRs are prohibited.
• Step 3: Neighborhood restrictions
  • Review HOA/Condo bylaws and rules. Even if city zoning allowed STRs (which it does not for <30 days), private covenants can independently prohibit short‑term rentals.
• Step 4: Tax obligations (if legally operating any transient lodging)
  • Register as needed for state and local taxes and obtain any required state lodging licenses. Confirm requirements with the Florida Department of Revenue, the Florida Department of Business and Professional Regulation (DBPR), and the Orange County Comptroller (local tourist development taxes).
• Step 5: Consider nearby, less restrictive markets
  • If STRs are central to your investment plan, evaluate municipalities with clearer allowances. Winter Park’s residential STR ban makes it unsuitable for conventional STR investments.

Required documents, permits, licenses, and guidelines

• For any legal rental operation in the city:
  • Business Certificate/Business Tax Receipt (BTR): Required to operate a business in Winter Park. [Source: City of Winter Park – Business Certificate] [Link: cityofwinterpark.org/departments/planning-zoning/business-certificate/]
• If you are legally authorized to operate transient lodging (which is not the case in residential zones under Section 58‑71(aa)):
  • State-level transient public lodging registration (if applicable): Florida DBPR; confirm current requirements and process on the DBPR website.
  • Sales and tourist development taxes: Florida Department of Revenue for sales tax, and Orange County Comptroller for local tourist development taxes; confirm tax rates and remittance rules with those agencies.
• Safety and code compliance:
  • Property standards are enforced under the International Property Maintenance Code and city ordinances. Be prepared to meet interior/exterior maintenance standards and to respond promptly to code complaints. [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]

Important: Because Winter Park prohibits rentals under one month in residential zones, you will not obtain an STR “license” from the city to lawfully operate a sub‑30‑day rental on a residential lot.

Specific regulations and enforcement (city, county, and state)

City of Winter Park (Orange County, Florida)

• Minimum stay: Rentals for less than one month are prohibited in residential zones. [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]
• Enforcement mechanism:
  • Complaints and inspections follow Florida Statutes Chapter 162. The city must notify the violator and allow reasonable time to correct before escalating to the Code Compliance Board. [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]
  • Daily fines: The Code Compliance Board can assess fines up to $250 per day per violation; repeated violations may increase to $500 per day. [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]
  • Anonymity limits: Per CS/SB 60 (effective July 1, 2021), anonymous complaints are not investigated unless there is an imminent threat to health or safety. [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]
• Code process:
  • Complaint filed → Case number assigned → Initial inspection → Notice to violator with time to cure → Hearing before the Code Compliance Board → Orders and potential fines. [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]
• Ordinance access:
  • The City Code (including Chapter 58 Land Development Code) is available via Municode. [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]

County level (Orange County, Florida)

• Tourist development and other local taxes may apply to transient lodging; consult the Orange County Comptroller’s Office for current rates, reporting, and registration. Because Winter Park prohibits STRs in residential zones, county tax compliance becomes relevant only if you are legally operating transient lodging elsewhere in Orange County or if your property is in a district where STRs are permitted.

State level (Florida)

• Local authority to regulate STRs via zoning and minimum stay rules is well established in Florida, and Winter Park’s prohibition has been repeatedly defended by the city. Florida Statutes Chapter 162 governs code enforcement procedures used by municipalities, and any state preemption questions should be resolved by consulting current statutes and local counsel. [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]

Additional sources (non‑local context)

• Town of Winter Park, Colorado content appears in the provided materials but pertains to a different jurisdiction. Do not apply Colorado rules to Florida investors.

Contact information (city authority in charge of STRs/code compliance)

• Safety & Code Compliance (Violations/Process inquiries):
  • Phone: 407‑599‑3600
  • Email: codecompliance@cityofwinterpark.org
  • Complaint form (for non‑anonymous complaints): cityofwinterpark.org/code-complaint [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]
• Noise disturbances or hazardous condition emergencies:
  • Phone: 407‑644‑1313 [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]
• City Hall (general information):
  • Address: 401 South Park Avenue, Winter Park, FL 32789
  • Phone: 407‑599‑3399 [Source: City of Winter Park – Safety & Code Compliance] [Link: cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/]
• Planning & Zoning (Business Certificate/BTR and zoning confirmation):
  • Phone: 407‑599‑3399 (City Hall) and ask to be transferred to Planning & Zoning
  • Business Certificate information: cityofwinterpark.org/departments/planning-zoning/business-certificate/ [Link: cityofwinterpark.org/departments/planning-zoning/business-certificate/]
• Orange County Comptroller (tourist development taxes, if applicable):
  • Phone: See Orange County Comptroller website (visit orangeclerk.org)
• Florida Department of Revenue (state sales tax registration, if applicable):
  • Phone: See Florida DOR website (visit fl revenue.com)
• Florida Department of Business and Professional Regulation (DBPR) (transient public lodging registration, if applicable):
  • Phone: See DBPR website (visit myfloridalicense.com)

Source links (for investors’ reference)

• City of Winter Park – Safety & Code Compliance (including STR prohibition, enforcement process, fines, and contact information): cityofwinterpark.org/departments/building-permitting-services/safety-code-compliance/
• City of Winter Park – Business Certificate (Business Tax Receipt): cityofwinterpark.org/departments/planning-zoning/business-certificate/
• City Code of Ordinances (Municode): library.municode.com/fl/winter_park/codes/code_of_ordinances
• Airbnb Community Thread – Winter Park STR enforcement reports: community.withairbnb.com/t5/Help-with-your-business/Short-term-rentals-in-Winter-Park-FL/m-p/1379104
• Ross Janke Real Estate Blog – STR overview (investor perspective, includes third‑party claims about commercial zones): rossjankerealestate.com/blog/winter-park-fl-short-term-rental-rules-what-investors-need-to-know

Compliance tip: If you discover or believe your property may qualify for an exception (e.g., nonconforming rights), obtain a written determination from Planning & Zoning before listing. Absent such confirmation, any stay of less than 30 days in a residential dwelling in Winter Park is a violation under Section 58‑71(aa) and will trigger enforcement.