Short-term rental rules in Orlando, Kissimmee and Davenport: licenses, taxes and zoning explained
The license almost every vacation home needs
Florida regulates vacation rentals under Chapter 509. If you rent a whole unit for stays under 30 days more than three times per year, you generally need a DBPR vacation rental license (~$230/year for a single unit), renewed annually, with basic safety requirements. Operating without one exposes the owner to fines and shutdown.
Zoning: the rule that surprises buyers the most
A beautiful home in the wrong neighborhood is a non-rentable home. Much of unincorporated Orange County and many traditional residential subdivisions prohibit rentals under 30 days. Osceola and Polk counties (Kissimmee, Davenport, ChampionsGate corridor) concentrate the communities zoned for short-term rental — which is why the region's resort communities (covered in our communities comparison) became the center of the market. Always verify zoning AND HOA rules before buying; an HOA can prohibit STR even where the county allows it.
Taxes on every booking — and who actually owes them
Osceola County requires collection and remittance of a 6% Tourist Development Tax on stays of six months or less, in addition to state and local sales taxes. Some platforms collect part of these taxes in some counties, but the owner or their management company remains legally responsible for registration and correct remittance. A professional manager handles registration, filing and remittance as part of the operation.
What compliance failure actually costs
It's not just fines: county enforcement can force cancellation of confirmed bookings, platforms can delist the property, and the HOA can impose penalties. Refunds, lost revenue and reputation damage usually cost far more than doing it right from day one.
The practical checklist
Before buying: confirm county zoning, city rules if incorporated, HOA covenants, and existing license transferability. After buying: DBPR license, county TDT account, state sales tax registration, and insurance rated for short-term rental use. Or hand the whole checklist to a manager who does this every week.