Florida · 21,005 licensed rentals
Orlando & Kissimmee vacation rentals, booked with the owner
Central Florida has more vacation homes than almost anywhere in the country, and most of them sit within a half hour of the big theme parks. Kissimmee and the US-192 corridor hold the classic pool-home communities, Davenport and ChampionsGate stretch west along I-4 with larger resort houses, and Orlando itself mixes condos near International Drive with homes close to downtown and the lakes.
Every property in this section holds an active Florida vacation rental license. We start each listing from the state record and the neighborhood around it. Owners who claim their listing add their own photos, rates and a direct booking link, so you deal with the family or manager who runs the home instead of a platform that adds its cut to every night.
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Areas in Orlando & Kissimmee
11578 licensed rentals Kissimmee Vacation rentals in Kissimmee 
7123 licensed rentals Davenport, ChampionsGate & Reunion Vacation rentals in Davenport 
2007 licensed rentals Orlando Vacation rentals in Orlando 
28 licensed rentals Winter Garden & Windermere Vacation rentals in Winter Garden 
269 licensed rentals Lakeland & Winter Haven Vacation rentals in Lakeland | Area | Best for | Homes | Condos | Total |
|---|---|---|---|---|
| Kissimmee vacation rentals | Families with kids, first Disney trips, private pool homes | 9,790 | 1,788 | 11,578 |
| Davenport, ChampionsGate & Reunion vacation rentals | Large groups, multi-family trips, golf, more house for the money | 5,999 | 1,124 | 7,123 |
| Orlando vacation rentals | Universal and SeaWorld trips, conventions, couples, small families | 893 | 1,114 | 2,007 |
| Winter Garden & Windermere vacation rentals | Quieter family stays, lake days, cyclists, longer visits | 21 | 7 | 28 |
| Lakeland & Winter Haven vacation rentals | LEGOLAND trips with young kids, spring training, lake stays, value | 245 | 24 | 269 |
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Orlando vacation rental questions
Are these rentals licensed?
Yes. Florida requires a vacation rental license from the Department of Business and Professional Regulation for any home or condo rented to guests more than three times a year for stays shorter than 30 days. Each listing here is built from an active license in that public record, and the license number appears on the listing.
Why book direct instead of through Airbnb or VRBO?
Since September 15, 2026, Airbnb charges most hosts a host-only fee of about 15.5% of every booking, and that cost is built into the nightly price you see. Booking with the owner keeps that fee out of the deal, and you get answers straight from the person who knows the house: pool heat, cribs and strollers, early check-in, parking for a second car.
Which area is closest to Walt Disney World?
The west end of the US-192 corridor in Kissimmee, Celebration, and the Lake Buena Vista side of Orlando are the closest, usually 10 to 20 minutes from the parks. Davenport and ChampionsGate are about 20 to 30 minutes out along I-4 and tend to offer bigger homes for the money. For Universal Orlando and SeaWorld, International Drive is the shortest trip.
How do I book a home that has no booking button yet?
Send an availability request from the listing. We forward it to the owner using the contact on their state license, and they reply to you directly. Listings with a "Book direct" button link to the owner's own booking page, where you pay them, not a middleman.