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Monticello, FL
Generally Investor Friendly
Local STR Agent

Yes, short-term rentals are allowed in Monticello, Florida. However, it is essential to understand that Monticello does not have specific city ordinances governing short-term rentals. Instead, operators must comply with Florida state regulations. The zoning data confirms that short-term rentals are a permitted use within the city, representing approximately 6.71% of land use allocation, indicating regulatory acceptance of this business model.
Starting a short-term rental business in Monticello requires careful planning and adherence to state-level regulations. The process begins with thorough market research, leveraging the area's proximity to Tallahassee and its appeal as a historic Southern town. Given the seasonal nature of the market—with peak demand during late fall through winter months and the annual Watermelon Festival in June—investors should strategically position their properties to capitalize on these predictable demand patterns.
The first step involves property acquisition and zoning verification. While short-term rentals are permitted use in Monticello, investors must confirm that their specific property is located in a zone that allows short-term rental operations. The Zoneomics data indicates that short-term rentals are integrated into the city's zoning framework, but local variations may exist.
1. Florida Business License
2. Tax Registration and Collection
3. Local Compliance Considerations
Essential Documentation:
Monticello operates under a permissive regulatory framework for short-term rentals. The absence of specific city ordinances means operators primarily operate under state guidelines and general municipal codes. However, the city's zoning framework explicitly acknowledges short-term rentals as a legitimate land use, providing regulatory certainty for investors.
Jefferson County, where Monticello is located, may have additional requirements not detailed in the provided content. Operators should verify county-level tax obligations and any potential local ordinances that might affect short-term rental operations.
1. Licensing Requirements
2. Tax Obligations
3. Operational Standards
A critical consideration for Monticello investors is the potential impact of private restrictions. The provided content explicitly notes that "some areas in Monticello may have Homeowner's Association (HOA) rules or deed restrictions that prohibit short-term rentals." This creates a significant due diligence requirement for investors:
Primary State Licensing Authority
Tax Collection and Remittance
Local Tax Administration
Local Zoning and General Administration
GoSummer - Monticello Vacation Rental Management: https://www.gosummer.com/vacation-rental-management/monticello-florida
Zoneomics - Monticello Zoning Data: https://www.zoneomics.com/zoning-maps/florida/monticello
Monticello's short-term rental market presents unique opportunities and challenges. The regulatory environment is relatively straightforward, with state-level oversight and permissive city zoning. However, investors must navigate private restrictions and seasonal market dynamics. The proximity to Tallahassee and the historic character of the area provide solid fundamentals for investment success.
The key to successful STR investment in Monticello lies in thorough pre-acquisition due diligence, strict regulatory compliance, and strategic positioning to capitalize on the area's seasonal demand patterns and unique attractions.

Monticello ( MON-tiss-EL-oh) is the only city and the county seat of Jefferson County, Florida, United States. The city is named after Monticello, the estate of the county's namesake, Thomas Jefferson, on which the Jefferson County Courthouse was modeled. The population was 2,589 at the 2020 census. Monticello is home to Indian mounds and many historic buildings, including the Perkins Opera House and Monticello Old Jail Museum.
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