Kissimmee vs Davenport short-term rental: how the two markets compare

Two markets, one county line apart

Kissimmee and Davenport are two of the most-searched names in the Orlando short-term rental (STR) conversation, and they sit barely a county line apart. Kissimmee is the seat of Osceola County; Davenport occupies the northeast corner of Polk County, inside the cluster of communities investors call Four Corners. For a buyer comparing them, the theme parks are a shared draw — the differences show up in tax rates, zoning language, and the price band your budget reaches.

This guide lays out those differences factually. None of it is a forecast or a promise about value; every figure below is an estimate that varies by property and moves with the market. Confirm the specifics of any parcel with your own advisors before you commit.

Geography: where each market sits

Kissimmee / Osceola: The county runs south and east of the main park corridor. Its US-192 corridor and resort-zoned pockets include some of the closest purpose-built vacation-home communities to the attractions, while Celebration and the St. Cloud side round out the county. Most STR activity concentrates in the western resort zones.

Davenport / NE Polk: Davenport sits where Osceola, Polk, Lake, and Orange counties nearly meet — the Four Corners area. Master-planned resort communities in the ChampionsGate and wider Four Corners cluster were built around vacation rentals. The drive to the parks is typically a short trip east and north; verify the exact distance and drive time for any address, since Four Corners spans several miles.

Short-term rental zoning posture

Osceola County uses resort and overlay zoning to designate where nightly rentals are permitted. Inside those districts, transient occupancy is an allowed use rather than an exception; outside them, STR may be restricted.

In Polk County, the Davenport resort communities were largely platted for vacation use, so short-term rental is commonly permitted at the community level. In both counties, permission is parcel-specific and layered with HOA covenants, licensing, and registration. Never assume a listing's marketing reflects the legal use — confirm the zoning, the HOA rules, and county and state licensing for the exact property before you buy.

Tourist Development Tax and other taxes

The clearest hard-number difference is the Tourist Development Tax (TDT), the local levy collected on stays under six months. Osceola County levies a 6% TDT, per the Osceola County Tax Collector, while Polk County levies 5%, per the Polk County Tax Collector. That single percentage point applies to gross rental revenue, so across a busy year it is a genuine line item rather than a rounding difference.

On top of TDT, both counties add Florida's state and local sales tax on transient rentals, and both operate in a state that levies no personal income tax. TDT and sales tax are typically collected from the guest and remitted by the host or booking platform; treat the mechanics as something to confirm with your accountant.

Price bands and what your budget reaches

On price, Osceola County's median sale price was roughly US$393,783, per Redfin (Osceola County Housing Market), 2026, with a working band of about US$300,000 to US$550,000 depending on zone and property type. Polk County's median was about US$305,000, per Redfin (Polk County Housing Market), February 2026, with Davenport's resort communities and the ChampionsGate and Four Corners area generally sitting in the upper part of a roughly US$300,000 to US$450,000 band.

In practice, comparable resort-style vacation homes in the two areas can land closer together than the county medians suggest, because each county figure blends very different housing stock. These are ranges and estimates, not a promise of value or appreciation; the right number for you depends on the specific home, community, and financing.

Taxes and structure for international buyers

International buyers are a meaningful share of both markets. Florida Realtors reported that international buyers paid a median of about US$442,000 in Florida, per Florida Realtors, 2025 — a figure that lands near the resort-home range in both counties.

Two tax points matter at the structuring stage. First, Florida levies no state personal income tax, which is part of why the state draws foreign investment. Second, when a foreign seller later sells, FIRPTA withholding is generally 15% of the sale price, per the IRS. Neither point is advice for your situation; ownership structure, financing, and tax planning should be worked out with a CPA and an attorney before you close.

How to choose between them

If your priority is the shortest, most established resort corridor and you can work with a 6% TDT, Osceola / Kissimmee is the tighter fit. If a lower entry price and a 5% TDT weigh more, Davenport's Four Corners communities are worth a close look. Either way, the deciding factors are parcel-level: zoning, HOA rules, licensing, projected occupancy, and total carrying cost.

Model those numbers for the specific home with a licensed agent and your tax advisor rather than choosing a county in the abstract. Flexway Realty can help you compare individual listings across both counties and verify the STR status of each before you make an offer.