Is my Kissimmee & Osceola County rental legal? Checklist

Permit / license / registration

• State license (Florida DBPR): Florida DBPR vacation rental / transient public lodging license (homestead room-rental exemptions may apply).
• City of Kissimmee: Rentals under 30 days in residential districts are prohibited unless in the Short Term Rental Overlay (STRO) with qualifying zoning/PUD approval or an approved conditional use (City Code 14-2-44, 14-2-64).

Zoning, where allowed & definitions

• State preemption: Florida law (s. 509.032(7)(b), F.S.) bars local rules adopted after June 1, 2011 from prohibiting vacation rentals or regulating rental duration/frequency; older local rules still apply.
• Unincorporated Osceola County: Confirm zoning allows STRs (STR overlay map / STRPD district), get a DBPR vacation rental license, then a Local Business Tax Receipt from the Osceola Tax Collector.

Night limits, minimum stays & occupancy

• Not listed on our page: Verify with the city/county before renting.

Fees, penalties & pending changes

• Fees & penalties: Verify with the city / county: permit and LBTR fee amounts.

Taxes & who collects them

• Register / account for FL state sales tax (6%)
• Register / account for Osceola County surtax (1.5%)
• Register / account for Local tourist/transient taxes (6%)
• What Airbnb collects: Airbnb collects state 6% + 1.5% surtax only. You must register with and remit the Osceola County 6% tourist development tax yourself.
• Vrbo and direct bookings: check which taxes Vrbo collects in your area; for direct bookings you collect and remit all of them yourself.
• Mandatory cleaning fees charged to guests are taxable as part of the rental (state, surtax and tourist tax). Only an optional, separately itemized fee the guest can decline is excluded (FL Admin. Code 12A-1.061).

Total rate: 13.5%. Osceola County tourist development tax is 6% (FL DOR DR-15TDT); surtax 1.5% (FL DOR DR-15DSS). Calculate.

HOA / condo check

• Read your declaration, bylaws and rules for rental bans, minimum terms, caps and approval requirements.
• Get any association sign-off or approval letter your city or association requires.
• See our HOA & condo guide.

Insurance

• Confirm your homeowner/condo policy covers short-term rental use, or add a short-term rental policy. Platform host protection is not a substitute for insurance.
• Ask your association whether it requires specific liability coverage.

Deadlines

• Renew city/county permits or registrations on their schedule (often annually): confirm the date with the office that issued it.
• Florida sales and transient rental tax returns: due the 1st, late after the 20th of the month after the reporting period.
• Property tax dates: see Florida deadlines.

Official sources

• Kissimmee Code 14-2-64 (short-term rental of residential dwellings)
• Kissimmee Code 14-2-44 (STR overlay district)
• Osceola County: STRPD and how to get an STR license
• Airbnb: Florida taxes it collects
• FL DBPR lodging licensing
• FL DOR transient rental tax rates

Want it done for you?

Get a personalized STR Compliance Check ($49) for your exact address in any US city: the permits, registrations and tax accounts you need, with official sources, delivered by email in 48 business hours. Not legal advice.

Stay Compliant: $4.99/month

Rules, tax rates and Airbnb/Vrbo policies can change without warning, and hosts who miss a change can be fined. Get alerts when your city, county or state changes, deadline reminders, a pending-bill watch list and a monthly host brief (even in quiet months: "we checked on [date]; no changes"). Compare plans.