Kissimmee is one of the most STR-friendly markets in Florida — and one of the highest-earning. Proximity to Disney World means year-round demand and premium nightly rates. But Osceola County and the City of Kissimmee both have licensing requirements you need to meet before your first guest checks in.
Here is the complete 2026 guide to getting your vacation rental license in Kissimmee, FL. Want it done for you? Our team handles the full process.
In Kissimmee and Osceola County, a short-term rental is defined as a dwelling unit rented for non-permanent use — specifically for periods not exceeding 30 days for the same individual within a 12-month period. Florida state law further defines STRs as any property rented more than 3 times per year for stays under 6 months.
Kissimmee is unique among Florida cities in that it is generally STR-permissive — the county does not restrict the number of properties an investor can own or limit LLC ownership structures.
Airbnb and VRBO handle remittance of these taxes in Osceola County for most listings. You must still register your own TDT account with the county.
All Kissimmee vacation rentals must comply with Florida Building Codes. Inspectors verify:
No cap on the number of STRs an investor can own. No restriction on LLC ownership structures. Year-round demand driven by Disney World, Universal Studios, and major convention events. Average annual occupancy rates consistently above 70% for well-positioned properties. For investors building a portfolio, Kissimmee is one of the most operator-friendly markets in the country.
Getting fully licensed in Kissimmee typically takes 3 to 5 weeks — faster than most Florida cities due to the county's relatively streamlined processes. DBPR inspection scheduling is usually the main delay.
Whether you are licensing a single property or building a portfolio near Disney, our team handles the entire Kissimmee licensing process — DBPR application, BTR, CUP coordination if needed, and TDT registration.
Contact us today and we'll get your Kissimmee vacation rental fully licensed and ready to earn.