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Search results; Over 1,000 homes in Kissimmee

Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds, 6 bathrooms
1–6 Sept
New place to stay
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 12 reviews
Townhouse in Kissimmee
Disney Retreat w/ Private Pool & Resort Access
5 bedrooms, 7 beds, 4.5 bathrooms
23–28 Aug
New place to stay
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds, 5 bathrooms
5–10 Sept
New place to stay
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
31 Oct – 5 Nov
New place to stay
Superhost
Home in Kissimmee
6 Bd/ 5 Ba/ Solara Resort (9038 Sr)
6 bedrooms, 11 beds, 5 bathrooms
6–11 Sept
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
3–8 Oct
4.92 out of 5 average rating, 12 reviews
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds, 2 bathrooms
25–30 Aug
New place to stay
Top guest favourite
Home in Kissimmee
Private Pool | Themed Rooms | Near Disney World!
5 bedrooms, 7 beds, 4 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 19 reviews
Superhost
Home in Four Corners
8 Bd/ 6 Ba/ Windsor Cay (1025 Bw)
8 bedrooms, 8 beds, 6 bathrooms
6–11 Sept
Home in Kissimmee
Chic 8BR All Suites with Pool and Game Room
8 bedrooms, 10 beds, 8 bathrooms
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Kissimmee
2026 NEW 06 Bedrooms at Solara Resort/Private Pool
6 bedrooms, 9 beds, 4.5 bathrooms
11–16 Jan
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Kissimmee
New Themed Luxury 08 Bedrooms At Encore Resort
8 bedrooms, 8 beds, 7 bathrooms
2–7 Sept
Superhost
Home in Four Corners
8BR house with private pool and game room
8 bedrooms, 8 beds, 6 bathrooms
24–29 Aug
New place to stay
Guest favourite
Townhouse in Kissimmee
Upstay Modern Home Near Disney with Pool
4 bedrooms, 5 beds, 4.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 13 reviews