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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Apartment in Kissimmee
O-Gated Resort-5 miles to Disney-2 FREE Water Park
2 bedrooms, 3 beds, 2 private bathrooms
5–10 Sept
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4.94 out of 5 average rating, 186 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
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
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
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
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
Superhost
Home in Kissimmee
7 Bd/ 6 Ba/ Storey Lake (4585 Tb)
7 bedrooms, 10 beds, 6 bathrooms
26 Sept – 1 Oct
New place to stay
Superhost
Home in Four Corners
8 Bd/ 6 Ba/ Windsor Cay (1025 Bw)
8 bedrooms, 8 beds, 6 bathrooms
6–11 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
Superhost
Home in Kissimmee
6 Bd / 3,5 Ba / Sleeps 22 / Reunion Village
6 bedrooms, 11 beds, 3.5 bathrooms
21–26 Aug
New place to stay
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds, 5 bathrooms
5–10 Sept
New place to stay
Villa in Kissimmee
Cumbrian Dream 4 Bedroom Pool Home near Disney
4 bedrooms, 6 beds, 3 bathrooms
25–30 Aug
Superhost
Home in Kissimmee
Luxury Villa /Movie Theater/Pool Heater/
3 bedrooms, 5 beds, 3 bathrooms
31 Aug – 5 Sept
Top guest favourite
Apartment in Kissimmee
Renovated Family Condo • Disney • Free Parking
2 bedrooms, 4 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 56 reviews
Superhost
Townhouse in Kissimmee
3 Bd/ 3 Ba/ The Hub At Westside (3228 Tt)
3 bedrooms, 4 beds, 3 bathrooms
21–26 Aug
Home in Kissimmee
Disney Dream Oasis 7br/4.5 Bath
7 bedrooms, 11 beds, 4 bathrooms
27 Aug – 1 Sept
New place to stay
Home in Kissimmee
Luxury Themed Retreat | Private Pool | 4mi-Disney
3 bedrooms, 6 beds, 2.5 bathrooms
22–27 Aug
New place to stay
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds, 2 bathrooms
25–30 Aug
New place to stay
Guest favourite
Townhouse in Kissimmee
5 Bd/ 4 Ba/ Storey Lake (4810 Sq. ft.)
5 bedrooms, 7 beds, 4 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 5 reviews