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Search results; Over 1,000 homes in Kissimmee

Guest favourite
Townhouse in Kissimmee
Disney Retreat w/ Private Splash Pool + Game Room
4 bedrooms, 7 beds, 3.5 private bathrooms
20–25 Aug
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4.92 out of 5 average rating, 144 reviews
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds, 4.5 bathrooms
14–19 Sept
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds, 5 bathrooms
16–21 Aug
New place to stay
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
New place to stay
Superhost
Home in Davenport
3BR Luxury Disney Escape | Hot Tub & 2 King Suites
3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Aug
New place to stay
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
2–7 Oct
New place to stay
Guest favourite
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Storey Lake (4285 Qs)
4 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Four Corners
8BR house at Windsor Cay Resort
8 bedrooms, 8 beds, 6 bathrooms
17–22 Aug
New place to stay
Superhost
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, 5 reviews
Guest favourite
Home in Kissimmee
Amazing Home Near Parks w/ Pool & Spa
4 bedrooms, 5 beds, 4 bathrooms
24–29 Oct
5.0 out of 5 average rating, 6 reviews
Guest favourite
Townhouse in Kissimmee
5 Bd/ 4 Ba/ Storey Lake (4810 Sq. ft.)
5 bedrooms, 7 beds, 4 bathrooms
25–30 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Flat in Kissimmee
3 Bd/ 2 Ba/ Storey Lake (3141-308 Pc)
3 bedrooms, 5 beds, 2 bathrooms
13–18 Aug
Superhost
Home in Kissimmee
4895 5BR home sleeps 14 Themed rooms | Storey Lake
5 bedrooms, 7 beds, 4 bathrooms
29 Aug – 3 Sept
New place to stay
Home in Davenport
Upstay Contemporary Retreat w Pool, BBQ & Backyard
5 bedrooms, 7 beds, 4 bathrooms
5–10 Oct
5.0 out of 5 average rating, 3 reviews
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
The Most Fun House, Tons of Room and a Huge Pool!
12 bedrooms, 24 beds, 15 bathrooms
15–20 Aug
New place to stay
Superhost
Home in Clermont
Experience Our New 2026 10BR Home at Windsor Cay
10 bedrooms, 12 beds, 8 bathrooms
13–18 Sept