Florida preempted local STR regulations in 2011 (later modified) but individual cities and counties retain authority to regulate STRs—Miami Beach bans STRs in most residential areas, while Orlando, Tampa, and Jacksonville have varying registration requirements. Before purchasing or listing any property, research your specific city and county ordinances by contacting the local planning department or checking your municipality's website—operating without proper registration results in fines of $500–$5,000 per day in enforcement-active markets. Florida requires all STR operators to collect and remit 6% state sales tax plus county discretionary surtax (typically 1–3%) on all rental income—Airbnb collects and remits this automatically in Florida. Register with the Florida Department of Revenue for sales tax purposes and with the county tourist development tax (TDT) office, as Airbnb may not remit the county TDT in all Florida counties.

Florida's top STR markets by revenue potential include: Miami Beach (high rates, strict regulation), Orlando (theme park proximity drives year-round occupancy), Tampa Bay (growing corporate and leisure market), Key West (premium rates, limited inventory), and Destin/30A (Gulf Coast beach demand). Use STR analytics platforms like AirDNA, Mashvisor, or Rabbu to analyze average daily rates (ADR), occupancy rates, and revenue per available room (RevPAR) for specific markets and property types before investing. A beachfront 3-bedroom in Destin might average $350/night with 75% annual occupancy ($95,000 ADR revenue), while an Orlando 4-bedroom near Disney averages $175/night with 80% occupancy ($51,000 ADR revenue)—both are strong markets with different guest profiles. Understand the seasonal demand curve for your target market: beach markets peak June–August and December, while Orlando runs strong year-round with slight peaks around school vacations.

Many Florida HOAs and condo associations prohibit or strictly limit short-term rentals—violations can result in fines, legal action, and forced cessation of your rental business. Review your HOA covenants, conditions, and restrictions (CC&Rs) before listing any property and look specifically for minimum rental period requirements (often 30 or 90 days), rental approval processes, and prohibitions on guest registration. If you rent rather than own, review your lease agreement for subletting restrictions—listing a rental on Airbnb without landlord permission is a lease violation that can result in eviction. If rental income is your goal and you are property-shopping, prioritize areas and properties in HOA-free or STR-permissive communities to avoid regulatory complications later.

Standard homeowner's insurance typically excludes coverage for commercial rental activity—notify your insurer of your STR plans and secure a short-term rental policy or endorsement. Airbnb provides AirCover for Hosts covering up to $3 million in property damage, but this is not a substitute for dedicated STR insurance that covers liability, lost income, and theft by guests. Providers like Proper Insurance, CBIZ, and Slice offer STR-specific policies at $1,500–4,000/year depending on property value and location—this is a non-negotiable business expense. Vrbo's liability protection covers $1 million per incident, and listing on both platforms provides complementary coverage, but dedicated STR insurance remains essential for comprehensive protection.