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Search results; Over 1,000 homes in Kissimmee

Superhost
Cottage in Kissimmee
*Cozy Tiny Home - Fall FUN! -resort fees waved!
1 bedroom, 1 bed, 1 private bathroom
21–26 Aug
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4.82 out of 5 average rating, 119 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
22–27 Aug
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
13–18 Sept
New place to stay
Townhouse in Kissimmee
Disney Retreat w/ Private Pool & Resort Access
5 bedrooms, 7 beds
23–28 Aug
New place to stay
Guest favourite
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Kissimmee
Themed 06 Bedrooms/Game Room/Private Pool
6 bedrooms, 10 beds
1–6 Sept
Superhost
Home in Four Corners
8 Bd/ 6 Ba/ Windsor Cay (1025 Bw)
8 bedrooms, 8 beds
6–11 Sept
Superhost
Home in Four Corners
8BR house with private pool and game room
8 bedrooms, 8 beds
24–29 Aug
New place to stay
Superhost
Home in Kissimmee
6 Bd/ 5 Ba/ Solara Resort (9038 Sr)
6 bedrooms, 11 beds
6–11 Sept
Guest favourite
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Storey Lake (4285 Qs)
4 bedrooms, 5 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 10 reviews
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds
5–10 Sept
New place to stay
Top guest favourite
Apartment in Kissimmee
Renovated Family Condo • Disney • Free Parking
2 bedrooms, 4 beds
5–10 Sept
5.0 out of 5 average rating, 56 reviews
Home in Kissimmee
Superhero HQ: Private Pool & Spa Near Disney
5 bedrooms, 6 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
14–19 Feb
5.0 out of 5 average rating, 5 reviews
Home in Kissimmee
Luxury Themed Retreat | Private Pool | 4mi-Disney
3 bedrooms, 6 beds
22–27 Aug
New place to stay
Guest favourite
Townhouse in Kissimmee
5 Bd/ 4 Ba/ Storey Lake (4810 Sq. ft.)
5 bedrooms, 7 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Clermont
Experience Our New 2026 10BR Home at Windsor Cay
10 bedrooms, 12 beds
13–18 Sept
Superhost
Flat in Kissimmee
Luxury Reunion Retreat Patio Views Near Disney
5 bedrooms, 6 beds
2–7 Sept
New place to stay
Superhost
Home in Kissimmee
2026 Brand New Themed 06 Bedrooms At Solara Resort
6 bedrooms, 2 beds
28 Nov – 3 Dec