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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Cottage in Kissimmee
Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!
1 bedroom, 2 beds, 1 private bathroom
21–26 Jun
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4.99 out of 5 average rating, 201 reviews
Home in Kissimmee
Orlando Dream Escape
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
New place to stay
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 2.5 bathrooms
3–8 Aug
New place to stay
Hotel in Kissimmee
Stay Near Theme Parks | 3 Units | Pets Are Welcome
3 bedrooms, 6 queen beds, 3 bathrooms
21–26 Jun
New place to stay
Superhost
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
29 May – 3 Jun
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Davenport
Private Pool, Golf Community, Near Disney
4 bedrooms, 6 beds, 2 bathrooms
21–26 Jun
New place to stay
Superhost
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
22–27 Aug
New place to stay
Guest favourite
Home in Clermont
Beautiful 5BR Themed Villa w/ Pool at Windsor Cay
5 bedrooms, 7 beds, 4 bathrooms
12–17 Sept
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
15–20 Aug
New place to stay
Guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5 bedrooms, 9 beds, 4.5 bathrooms
1–6 Dec
5.0 out of 5 average rating, 12 reviews
Superhost
Townhouse in Clermont
Mario Arcade & Wizard Magic @ Windsor Cay
5 bedrooms, 8 beds, 5.5 bathrooms
12–17 Oct
New place to stay
Superhost
Townhouse in Kissimmee
4 BD/ 3 BA/ Storey Lake (4285 QS)
4 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
New place to stay
Superhost
Townhouse in Kissimmee
5 BD/ 4 BA/ Story Lake (4810 ML)
5 bedrooms, 7 beds, 4 bathrooms
28 Jun – 3 Jul
New place to stay
Top guest favourite
Flat in Kissimmee
Top1% *La Piu Belle* Retreat at Storey Lake View
2 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
4.96 out of 5 average rating, 206 reviews
Superhost
Home in Kissimmee
Stylish Home with Pool Hot Tub and Parking
5 bedrooms, 9 beds, 2.5 bathrooms
21–26 Jun
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
Magical 5BR Resort Amenities | Pool•BBQ•NearDisney
5 bedrooms, 7 beds, 5 bathrooms
19–24 Jun
Home in Kissimmee
Disney Area Home | Pool | Hot Tub | Themed Rooms
5 bedrooms, 9 beds, 4.5 bathrooms
21–26 Jun
5.0 out of 5 average rating, 4 reviews
Home in Kissimmee
FREE heated pool near Disney sleeps 8(4BR)-14(7BR)
7 bedrooms, 10 beds, 4 bathrooms
22–27 Jun
New place to stay
Cottage in Kissimmee
Blue Moon Cottage near Disney + Waterpark Access
8 bedrooms, 11 beds, 9 bathrooms
3–8 Aug