Two credible sources will tell you two very different things about the Kissimmee short-term rental market. One puts annual occupancy near 68 to 75 percent with typical revenue around $42,000. Another, working from the April 2025 to March 2026 window, reports 45.9 percent occupancy and $37,105 in annual revenue across 8,727 active listings, with supply up 106 percent year over year. Both numbers are defensible. Neither describes a house you can actually buy.
That gap is the entire point of this post. Kissimmee is not a single market with a middle. It is two markets stapled together by a zip code, and the line between them is drawn by zoning, HOA covenants, and municipal boundaries that most out-of-state buyers only discover after they own the wrong parcel.
The Kissimmee STR "average" is a blend of homes legally producing $60,000 to $120,000 a year and homes legally producing zero. Averaging them creates a number that describes no actual property. Your yield is set the moment you pick the address, not the moment you list.
Lead With the Zoning Line, Not the Listing
Osceola County permits short-term rentals only inside designated STR Overlay Districts or Short-Term Rental Planned Development (STRPD) zones. Standard residential designations such as R-1 and R-2 treat nightly rental as a commercial use that is not permitted. A home three blocks outside the overlay is not "harder to rent." It is not rentable at all as a vacation home, and code compliance in Osceola treats operating without the correct zoning as a violation carrying fines starting around $500, plus a mandated stop of activity.
The state framework does not save you. Florida Statute §509.032(7)(b) prevents cities and counties from banning vacation rentals in general or capping stay length, but it does not override zoning classifications that predate 2011 preemption, and it does nothing about a parcel that was never zoned for the use in the first place. SB 280, which would have centralized regulation under the state, was vetoed by Governor DeSantis in June 2024, so the 2011 preemption plus the local patchwork is still what governs a 2026 purchase.
What the Citywide Averages Are Actually Averaging
The 8,727 active listings AirROI counts across Kissimmee include hosts operating in overlay zones, hosts operating illegally in residential zones, condos in program-restricted resorts, and homes in HOAs that quietly prohibit nightly rental. When you average that pool, you get a mid-market number that only exists on a spreadsheet.
| Data view | Occupancy | Annual revenue | What it actually describes |
|---|---|---|---|
| Citywide, April 2025–March 2026 | 45.9% | $37,105 | Blend of 8,727 listings including underperformers and non-eligible parcels |
| Legacy market summaries | 68–75% | ~$42,000 | Pre-supply-surge pool, weighted toward active resort listings |
| Large resort pool homes, peak season | Higher on group bookings | Nightly $500–$900 on 6–9BR homes | Purpose-built product in Reunion and ChampionsGate |
Supply grew 106 percent over the trailing year, and yet ADR and revenue both trended up. That is not a saturated market. That is demand still absorbing new inventory, but it does mean the average now sits lower than the 2022 to 2023 numbers still floating around older investor guides.
Four Municipalities, One County, Four Rulebooks
Same county, same tax collector, four completely different answers depending on which side of a boundary line the parcel sits on:
- City of Kissimmee. Generally permissive in commercial and mixed-use zones, but requires a municipal license on top of the county Local Business Tax Receipt. Zoning, Environmental Health, and Building all sign off before issuance.
- Celebration. Prohibits short-term rentals outright. The address may look Disney-adjacent on a map. The covenants are the whole story.
- St. Cloud. Restricts STR to hotel and motel zones only. Buyers who assumed "Osceola County equals STR-friendly" have paid code enforcement to learn otherwise.
- Poinciana. Deed restrictions enforce a $100 per day fine schedule against nightly rentals. The community is popular with long-term buyers for a reason.
Unincorporated Osceola inside an STR Overlay or STRPD is the version of "Kissimmee" that produces the returns the market is known for. Everything else is a different investment.
The HOA Trap Sitting Under Everything
Florida's preemption statute does not reach HOA and condo governing documents. CC&Rs sit entirely outside §509.032, and they can prohibit nightly rental, impose 30 or 90-day minimums, cap the percentage of rented units, or require on-site management, regardless of what the city or county permits. This is the single most expensive surprise in the local investor experience, because it typically surfaces after closing when a neighbor complaint triggers a board letter.
The practical rule is simple. Read the recorded CC&Rs and any current rental amendments before removing an inspection contingency, not after. In resort communities that were purpose-built for the use, the CC&Rs usually align with the zoning. In communities that look like a resort from the road but were platted as residential, they often do not.
What Your Dollar Actually Buys, Community by Community
The purpose-built resort corridor is where the productive inventory concentrates. Product design itself is a revenue driver here, because 4 to 12-bedroom homes with private screened pools, themed rooms, and resort amenity packages can be booked by multiple families at once and command nightly rates well above the citywide ADR of $276.
| Community | Position | What the buyer is actually purchasing |
|---|---|---|
| Reunion Resort | Premium tier, three signature courses (Watson, Nicklaus, Palmer), water park | Larger tickets, higher HOA and membership fees, deepest guest profile |
| ChampionsGate (The Retreat) | STR-focused section of the master plan, off I-4 Exit 58 | Newer product, direct interstate access for drive markets, ~20 min to Disney gates |
| Storey Lake | Modern townhomes and single-family with lazy river and clubhouse | Mid-tier entry, high visibility on OTA platforms |
| Solara Resort | Recent build, indoor beach theme | Strong peak-season demand, well-represented on Airbnb and VRBO |
| Windsor Island / Windsor at Westside | Family-oriented resort amenities, pool homes | Deep AirDNA comps at the community level for DSCR underwriting |
| Windsor Hills | Closest to Disney, roughly 5 minutes to the gates | Older stock, smaller footprints, lower entry price |
The ChampionsGate footprint sits partly in Davenport and Polk County, and Reunion crosses jurisdictional lines. Always verify the taxing authority and the specific STR overlay for the parcel, not the community name on the marketing brochure.
Reading the 2026 Numbers Without Getting Fooled
Gross cap rates for well-chosen Kissimmee STRs are typically quoted in the 7 to 9 percent range. After 20 to 35 percent management, HOA dues that can run several hundred dollars a month in resort communities, insurance, and maintenance, net returns generally land between 4 and 6 percent. Any pro forma that shows more than that on paper is almost always using peak-month occupancy against a full-year expense base.
Financing math matters here because most out-of-state buyers use DSCR loans that qualify on projected rents rather than personal income. As of June 2026, STR DSCR rates in this corridor start around 5.8 percent on a 30-year fixed with 20 to 25 percent down, and underwriters lean on AirDNA community-level comps. That is another reason the STR-zoned resort corridor tends to close cleanly and general-residential parcels do not: the comp file simply is not there for a home the underwriter cannot legally assume will be rented nightly.
Seasonality behaves differently here than in beach or ski markets. Peaks land in March for spring break, June through August, and Christmas through New Year's. September and February are the soft months. Because theme park demand is structural rather than event-driven, the curve is flatter than most vacation markets, but any pro forma built on peak months alone is going to disappoint in the shoulders.
Before You Write an Offer
A workable pre-offer checklist for a Kissimmee STR looks like this:
- Confirm in writing from Osceola County Growth Management that the parcel sits in an STR Overlay District or STRPD zone.
- Pull the recorded HOA or condo CC&Rs and any rental amendments and read the nightly-rental language yourself.
- Verify the municipal jurisdiction. Kissimmee city limits, unincorporated Osceola, Celebration, St. Cloud, and Polk County all trigger different rulebooks.
- Budget for the two-license stack: DBPR vacation rental license, plus the Osceola County STR license at roughly $410 to start and $150 to renew annually. Add the municipal license if applicable.
- Confirm $1 million liability insurance capacity, a compliant floor plan showing safety equipment, and the guest-register recordkeeping requirement of three years.
- Model the deal at 45 to 55 percent occupancy for a stabilized year, not 68 percent. If the numbers work there, the peak-season upside is a bonus rather than a requirement.
- Register with the Florida Department of Revenue for the 6 percent state sales tax and with the Osceola County Tax Collector for the tourist development tax before the first booking.
FAQ
If the citywide average is $37,000, why do investors still buy here?
Because the average is the wrong number to look at. The productive inventory sits inside purpose-built resort communities where 6 to 9-bedroom pool homes book group families at $500 to $900 per night in peak season, and the depth of AirDNA comp data at the community level makes underwriting reliable. The average blends those homes with parcels that should never have been marketed as STRs in the first place.
Can an HOA really override county zoning?
Yes. Florida's preemption statute limits what cities and counties can do, but it explicitly does not reach HOA or condo governing documents. A community whose CC&Rs prohibit nightly rental can enforce that prohibition even if the parcel is inside a permissive zoning overlay.
Is Osceola County likely to tighten STR rules in 2026?
The 2011 preemption framework plus the local patchwork continues into 2026 after Governor DeSantis vetoed SB 280 in June 2024. The Osceola County Board of County Commissioners agenda is the practical place to watch for any proposed local ordinance activity, since state-level changes are the less immediate risk.
What is the fastest way to disqualify a listing before touring?
Two documents: the parcel's zoning classification from Osceola County, and the HOA's rental provisions. If either one says no, the pro forma is irrelevant.
Buying a vacation rental sight unseen is a normal transaction here, and it works when the address is vetted before the offer, not after. If you want a second set of eyes on a specific parcel, community, or pro forma before you commit, the Jim McQuade team walks investors through zoning, CC&R, and community-level comp review as a standard part of buyer representation. Schedule a consultation and bring the address.
