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Search results; Over 1,000 homes in Kissimmee

Guest favourite
Home in Kissimmee
Cozy House with Pool. Kissimmee/Orlando
3 bedrooms, 5 beds, 2 private bathrooms
29 Aug – 3 Sept
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4.91 out of 5 average rating, 272 reviews
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds, 4.5 bathrooms
14–19 Sept
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
2–7 Oct
New place to stay
Home in Clermont
New! Windsor Cay Resort | Private Pool | 5BR/5.5BA
5 bedrooms, 6 beds, 5.5 bathrooms
16–21 Aug
New place to stay
Superhost
Home in Four Corners
2026 BRAND NEW 08BD At Windsor Cay
8 bedrooms, 8 beds, 6 bathrooms
15–20 Aug
New place to stay
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
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds, 2 bathrooms
11–16 Aug
New place to stay
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Four Corners
8 Bd/ 6 Ba/ Windsor Cay (1025 Bw)
8 bedrooms, 8 beds, 6 bathrooms
19–24 Aug
Superhost
Home in Kissimmee
2026 6BR Themed Home w/ LED Pool at Solara Resort
6 bedrooms, 8 beds, 4.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
5Bed/4Bath Luxurious Privacy
5 bedrooms, 6 beds, 3.5 bathrooms
16–21 Aug
New place to stay
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Lucaya Village (8-101)
4 bedrooms, 7 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Kissimmee
Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
3 bedrooms, 5 beds, 2 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 40 reviews
Home in Kissimmee
Simply Magical | 13 PPL | Pool | Mini Golf | Games
4 bedrooms, 6 beds, 3 bathrooms
19–24 Aug
New place to stay
Superhost
Home in Kissimmee
9BR Pixar Theater Game Room | Pool Spa | Sleeps 27
9 bedrooms, 19 beds, 5 bathrooms
11–16 Aug
New place to stay
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
New place to stay
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
7–12 Mar
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
Home in Kissimmee
Modern Disney Villa • 7BR • Private Pool
7 bedrooms, 9 beds, 6.5 bathrooms
11–16 Aug