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Search results; Over 1,000 homes in Kissimmee

Superhost
Boutique hotel in Kissimmee
2-bedroom/2-bath suite Sleeps 12 - Near Disney
2 bedrooms, 6 beds, 2 private bathrooms
17–22 Aug
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5.0 out of 5 average rating, 4 reviews
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds
14–19 Sept
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
23–28 Aug
5.0 out of 5 average rating, 3 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
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds
16–21 Aug
New place to stay
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds
12–17 Aug
New place to stay
Superhost
Home in Four Corners
8BR house at Windsor Cay Resort
8 bedrooms, 8 beds
17–22 Aug
New place to stay
Superhost
Home in Four Corners
8 Bd/ 6 Ba/ Windsor Cay (1025 Bw)
8 bedrooms, 8 beds
19–24 Aug
Superhost
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, 3 reviews
Superhost
Flat in Kissimmee
3 Bd/ 2 Ba/ Storey Lake (3141-308 Pc)
3 bedrooms, 5 beds
12–17 Aug
Guest favourite
Home in Kissimmee
Amazing Home Near Parks w/ Pool & Spa
4 bedrooms, 5 beds
24–29 Oct
5.0 out of 5 average rating, 5 reviews
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, 7 reviews
Home in Clermont
New! Windsor Cay Resort | Private Pool | 5BR/5.5BA
5 bedrooms, 6 beds
16–21 Aug
New place to stay
Top guest favourite
Home in Kissimmee
Stylish Disney Retreat | 15 Mins to Disney
3 bedrooms, 4 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Kissimmee
7490 Magic Village 8 guests 4,5 baths 8 min Disney
4 bedrooms, 6 beds
12–17 Aug
5.0 out of 5 average rating, 3 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds
2–7 Oct
New place to stay
Superhost
Home in Clermont
7 Bd/ 5.5 Ba/ Windsor Cay (1099 Op)
7 bedrooms, 11 beds
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Villa in Kissimmee
Spacious villa w/pool & spa & game room
5 bedrooms, 7 beds
27 Dec – 1 Jan
5.0 out of 5 average rating, 4 reviews
Home in Davenport
Upstay Contemporary Retreat w Pool, BBQ & Backyard
5 bedrooms, 7 beds
5–10 Oct
5.0 out of 5 average rating, 3 reviews