Last verified: October 21, 2026
Orlando / Kissimmee is not one rulebook. Whole-home nightly rentals are legal only where zoning allows them. In the City of Orlando, short stays are limited to registered, owner-occupied home sharing. Unincorporated Orange County limits single-family transient rentals to R-3 zoning (or a PD that expressly permits them). Osceola County and the City of Kissimmee allow short-term rentals inside their designated short-term rental overlay and resort-zoned areas, which is where most of the vacation-home supply near Disney sits.
I'm Troy Nowak, broker of Mangrove Bay Realty (BK3436609). I help investors underwrite STR deals across Florida, including the Orlando / Kissimmee resort corridor. This guide covers the current rules, why resort zoning creates an edge for the right homes, and what 1- to 5-bedroom homes are selling for versus the revenue AirROI and Rabbu report for the same bedroom count.
Review STR Deal: Send the address and asking price and I will check the legal stay path for that property before you offer.
Why the rules create an edge in Orlando / Kissimmee
Most of metro Orlando's residential land does not allow whole-home stays under 30 days. Legal nightly product concentrates in Osceola County's short-term rental overlay and STRPD resort communities, Kissimmee's STRO district, and a small set of Orange County zones. That supply ceiling, plus year-round theme-park demand, favors buyers who confirm zoning first. It also means many homes listed as "Airbnb-ready" outside those zones are not.
Short-term rental rules in Orlando / Kissimmee
- City of Orlando. Owner-occupied home sharing only: stays under 30 days, one booking at a time, host lives on site and is present, no more than half the dwelling rented, and no more than 4 unrelated guests (or 2 per room, whichever is less). Registration fee is $275 the first year, then $100 a year (owner lives on the property) or $125 (non-owner occupied). Renting an entire home is generally not allowed unless the use qualifies as a Commercial Dwelling Unit in a permitted zoning district with a Business Tax Receipt. Ordinance effective July 1, 2018.
- Unincorporated Orange County. "Short-term rental" (179 days or less) is permitted only in C-1, C-2, C-3, I-1A, I-1/I-5, I-2/I-3, and I-4 districts, or in a Planned Development that expressly permits it. Single-family transient rental (under 30 days) is permitted only in R-3. All other districts prohibit both.
- Osceola County (unincorporated). Short-term rentals are allowed only where zoning permits them: the Short Term Rental Planned Development (STRPD) district, Commercial Tourist (CT) zoning limited to the Short Term Rental Overlay boundary, or approved subdivisions/PDs. Steps: confirm zoning on the county STR overlay map, get a Florida DBPR vacation rental license, then register a Local Business Tax Receipt with the Osceola County Tax Collector.
- City of Kissimmee. Rentals under 30 days in residential districts are prohibited except in the Short-Term Rental Overlay (STRO) with an eligible underlying district (SRPUD, MUPUD, RA-4, RB-1, RB-2, RC-1, RC-2), with conditional use approval where required, or under an approval that predates the overlay.
- Taxes. Orange County and Osceola County each levy a 6% tourist development tax on stays of six months or less, on top of Florida's 6% state sales tax and any county discretionary surtax.
- State framework. Florida Statute 509.032(7) preempts local bans adopted after June 1, 2011, but the zoning limits above that predate it remain enforceable. HOA and deed restrictions can still block use.
Official sources: City of Orlando Home Sharing Registration; Orlando Code Sec. 58.989–58.990; Orange County Zoning Division FAQ; Osceola County STRPD and STR license steps; Osceola LDC Table 3.3; Kissimmee Code § 14-2-64 and § 14-2-44 STRO; Florida DOR tourist development tax rates; Osceola County Tax Collector TDT. Rules change. Verify the exact parcel before you offer.
Price vs revenue by bedroom (Kissimmee)
Kissimmee is the core of the resort corridor and has the deepest bedroom-level data. Sold prices are trailing 12-month medians from closed MLS sales for all of Kissimmee (all property types, so they include homes outside STR zoning). Average sold price by bedroom is not available from a public source; the median is used instead. Revenue figures are trailing 12-month averages from AirROI (to September 2026) and Rabbu (as of April 27, 2026). Yields are gross (revenue ÷ median sold price) and exclude operating costs, financing, insurance, HOA, and taxes. Troy's benchmark is 20%+ gross yield.
| Bedrooms | Median sold price (12 mo) | AirROI avg annual revenue | Rabbu avg annual revenue | Approx. gross yield (AirROI / Rabbu) |
|---|---|---|---|---|
| 1 | $130,000 | $13,300 | $12,329 | 10.2% / 9.5% |
| 2 | $247,646 | $29,000 | $26,269 | 11.7% / 10.6% |
| 3 | $319,990 | $28,100 | $28,825 | 8.8% / 9.0% |
| 4 | $388,135 | $36,100 | $36,827 | 9.3% / 9.5% |
| 5 | $540,000 (5+ bed) | $58,900 (5+ bed) | $47,333 | 10.9% / 8.8% |
Sources: Florida Lux Real Estate Kissimmee market snapshot (median sale price by bedrooms, trailing 12 months of closed MLS sales, checked October 21, 2026); AirROI Kissimmee report (average annual revenue by home size, 12 months to September 2026); Rabbu Kissimmee market data (average annual revenue by property size, as of April 27, 2026). The 5-bedroom sold price and AirROI figure are 5+ bedroom buckets; Rabbu reports 5-bedroom homes separately and lists 6+ bedroom homes at $62,385. 5-bedroom-only median sold price: not available. City of Orlando bedroom data is omitted because whole-home nightly rentals are generally not allowed there.
None of the five bedroom counts reaches a 20% gross yield on a citywide median price. The math gets closer only when you buy below the median inside the STR overlay, or when a larger resort home outperforms the average. Underwrite the specific community, not the city average.
Seasonality
Rabbu's monthly averages for Kissimmee peak in March ($5,220) and July ($4,517), with the low in September ($1,378). AirROI shows the same shape: July ($5,490) and March ($4,990) lead, September ($2,780) is lowest, and average occupancy is 47.8% at a $288 ADR over the 12 months to September 2026. Plan cash reserves for late August through November.
Sources: Rabbu Kissimmee; AirROI Kissimmee.
Top attractions
- Walt Disney World Resort (Lake Buena Vista / Bay Lake), the main demand driver for Kissimmee and Four Corners rentals
- Universal Orlando Resort and Epic Universe
- SeaWorld Orlando and International Drive
- Old Town and the Kissimmee lakefront
- Orange County Convention Center (business and event demand)
- Orlando International Airport (MCO)
Who gets compressed and who gains the advantage
Who gets compressed: Buyers who assume any Orlando or Kissimmee home can run nightly, homes in City of Orlando residential zones, and anyone who underwrites a large home on citywide averages without checking the community's zoning and HOA rules.
Who holds the edge: Homes inside Osceola's STR overlay / STRPD resort communities or Kissimmee's STRO with clean DBPR and tax registrations, strong pool and theming amenities (Rabbu reports a pool at 88% of Kissimmee listings), and pricing that holds up in the September trough.
Due-diligence checklist
- Confirm the jurisdiction (City of Orlando, unincorporated Orange, City of Kissimmee, or unincorporated Osceola) on the county property appraiser site. A Kissimmee mailing address is not proof of city limits.
- Check the zoning district and the STR overlay map, then get written confirmation from the zoning office.
- Read the HOA / community documents for rental minimums, registration, and guest caps.
- Verify the DBPR vacation rental license path, Osceola LBTR (if applicable), and county tourist development tax account.
- Pull flood zone and full insurance quotes that disclose short-term rental use.
- Model peak and September months, and a 30+ day fallback where nightly use is not allowed.
Official sources
- City of Orlando Home Sharing Registration
- Orange County Zoning Division
- Osceola County STRPD and STR license steps
- City of Kissimmee Code § 14-2-64
- Florida DOR tourist development tax rates
- Florida DBPR vacation rental license
Buying or selling a short-term rental in Orlando or Kissimmee? Send the address through the contact form and I'll tell you which rules control it and whether the numbers work for your strategy.
Related: Pinellas County STR Market Guide · Tampa STR market guide · Florida STR occupancy scarcity · Troy Nowak agent profile
Hero photo: Lake Eola and the downtown Orlando skyline by JER3L1337, CC BY 4.0, cropped.
Educational real estate information, not legal, tax, or insurance advice. City and county rules, fees, and insurance costs change. Verify the exact parcel with the city, county, state, your insurer, and your association before you buy.