Market report · Updated November 2026
Orlando (Kissimmee) vacation rental market
What drives group travel here, when it peaks, and the local rules an owner or investor needs to know.
Quick answer
Kissimmee is one of the most established vacation-home markets in the country, built around Walt Disney World and the Orlando theme parks. Large groups choose homes with pools over several hotel rooms. Owners collect Osceola County's 6% tourist development tax on top of Florida sales tax, and need a state vacation rental license plus the right local business tax receipt.
At a glance
| Main demand | Theme parks, family vacations, sports and bowl games |
|---|---|
| Busiest months | Spring break, summer and the holidays |
| Occupancy tax | 6% Osceola tourist tax plus Florida sales tax and county surtax |
| Permit | Florida vacation rental license and a local business tax receipt |
| Group-home fit | Very strong, but also very competitive |
What drives demand
Theme parks
Disney, Universal and SeaWorld bring families year-round. Big groups want one house with a pool and a game room near the parks.
Holidays and events
Holiday parties at the parks, bowl games at Camping World Stadium and youth sports at ESPN Wide World of Sports add demand.
International visitors
Visitors from Latin America, the UK and Canada book long stays, often as multi-generation groups.
Busy and quiet months
| Months | Demand | Why |
|---|---|---|
| Spring break weeks, from mid-March | Peak | Spring break. |
| June to August | Peak | Summer school holidays, despite heat and storms. |
| Thanksgiving to early January | Busy | Holiday events and bowl games. |
| September and early November | Quiet | After school starts and during hurricane season. |
See what's on in Orlando (Kissimmee) for upcoming events that drive bookings.
What works for group homes
Six-bedroom homes with a private pool, themed kids' rooms and a game room compete best. Supply is high, so photos, reviews and pricing discipline decide occupancy. Resort communities with clubhouses and water parks can earn a premium.
Permits and taxes
Tourist development tax
Osceola County charges a 6% tourist development tax on short-term rentals. Owners or their agents collect and remit it to the county tax collector; some platforms do not collect it for you.
State sales tax
Florida's transient rental tax and the county's discretionary surtax apply as well. Confirm the current rates with the Florida Department of Revenue.
Licensing
Florida vacation rentals need a license from the state Department of Business and Professional Regulation, plus a city or county business tax receipt depending on where the home is. Only some zones allow short-term rentals, so confirm zoning before you buy.
What to watch
- Heavy supply: many similar homes compete on price.
- Hurricane season affects insurance and bookings.
- Community association rules can restrict rentals.
Run the numbers
Estimate a home's income with the vacation rental income calculator, then check the deal with the cap rate and DSCR calculators.
Sources
Other markets
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