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Search results; Over 1,000 homes in Kissimmee

Superhost
Boutique hotel in Kissimmee
2-bedroom/2-bath suite Sleeps 10 - 2 miles to WDW
2 bedrooms, 5 beds, 2 private bathrooms
10–15 Aug
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4.91 out of 5 average rating, 11 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
Simply Magical | 13 PPL | Pool | Mini Golf | Games
4 bedrooms, 6 beds
10–15 Aug
New place to stay
Home in Kissimmee
Modern Disney Villa • 7BR • Private Pool
7 bedrooms, 9 beds
10–15 Aug
Guest favourite
Home in Kissimmee
2026 NEW 06 Bedrooms at Solara Resort/Private Pool
6 bedrooms, 9 beds
4–9 Oct
5.0 out of 5 average rating, 16 reviews
Superhost
Home in Kissimmee
4895 5BR home sleeps 14 Themed rooms | Storey Lake
5 bedrooms, 7 beds
29 Aug – 3 Sept
New place to stay
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds
10–15 Aug
New place to stay
Home in Kissimmee
4BR Kissimmee home with private pool
4 bedrooms, 5 beds
23–28 Aug
New place to stay
Superhost
Home in Davenport
Luxury 7-BD Villa - Pool, Theater, and Game Room
7 bedrooms, 14 beds
23–28 Aug
New place to stay
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Davenport
Home Away from Home + 2 suites
5 bedrooms, 6 beds
18–23 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Kissimmee
NEW! Disney-Themed Escape | Private Pool | Villans
8 bedrooms, 13 beds
18–23 Aug
5.0 out of 5 average rating, 7 reviews
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Lucaya Village (8-101)
4 bedrooms, 7 beds
30 Aug – 4 Sept
Superhost
Home in Kissimmee
Windsor Hills, Disney/Universal, Extended Pool/SPA
4 bedrooms, 5 beds
10–15 Aug
Superhost
Home in Kissimmee
2026 Brand New Themed 06 Bedrooms At Solara Resort
6 bedrooms, 2 beds
28 Nov – 3 Dec
Home in Kissimmee
Chic 8BR All Suites with Pool and Game Room
8 bedrooms, 10 beds
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
7–12 Mar
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds
28 Nov – 3 Dec