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Search results; Over 1,000 homes in Kissimmee

Guest favourite
Cottage in Kissimmee
Cozy Cottage 5mins From Disney Parks!
1 bedroom, 2 beds, 1 private bathroom
26–31 Aug
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4.8 out of 5 average rating, 136 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
New place to stay, 7 bedrooms, 6 beds, 4.5 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
Superhost
Home in Four Corners
Family Home w/ Pvt Pool & Game Room | Walk to Club
New place to stay, 5 bedrooms, 7 beds, 4.5 bathrooms
27 Jul – 1 Aug
Home in Kissimmee
Poolside Heaven in Cumbrian Lakes
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 6 beds, 3 bathrooms
22–27 Aug
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
New place to stay, 5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
Superhost
Home in Kissimmee
Amazing 6-bedroom home with private spa
New place to stay, 6 bedrooms, 6 beds, 5.5 bathrooms
20–25 Aug
Superhost
Townhouse in Kissimmee
4 Bedrooms / 3 Bathrooms / Storey Lake (4821DS)
4 bedrooms, 6 beds, 3 bathrooms
26–31 Jul
Superhost
Home in Kissimmee
13-Min Disney | Priv Pool | 5BR Storey Lake Resort
5 bedrooms, 4 beds, 4 bathrooms
2–7 Aug
Superhost
Home in Kissimmee
2026 Brand New Themed 06 Bedrooms At Solara Resort
6 bedrooms, 2 beds, 5 bathrooms
19–24 Dec
Top guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5.0 out of 5 average rating, 16 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
5–10 Jan
Home in Kissimmee
Magical Villa with Themed Bedrooms at Reunion
New place to stay, 6 bedrooms, 10 beds, 5 bathrooms
27 Jul – 1 Aug
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
New place to stay, 5 bedrooms, 7 beds, 4.5 bathrooms
10–15 Aug
Superhost
Home in Kissimmee
Magic Palms Villa
5.0 out of 5 average rating, 4 reviews, 6 bedrooms, 9 beds, 3 bathrooms
16–21 Aug
Superhost
Home in Kissimmee
Magic Escape Orlando
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 3 bathrooms
8–13 Aug
Superhost
Home in Four Corners
Windsor Westside Cozy 8BR Villa, Lake View, Pool
New place to stay, 8 bedrooms, 10 beds, 6 bathrooms
11–16 Aug
Top guest favourite
Home in Kissimmee
NEW! Disney-Themed Escape | Private Pool | Villans
5.0 out of 5 average rating, 5 reviews, 8 bedrooms, 13 beds, 6 bathrooms
9–14 Aug
Superhost
Townhouse in Kissimmee
5 BD/ 4.5 BA/ Windsor at Westside (2015 MD)
New place to stay, 5 bedrooms, 7 beds, 4.5 bathrooms
26–31 Jul
Home in Kissimmee
Chic 8BR All Suites with Pool and Game Room
5.0 out of 5 average rating, 3 reviews, 8 bedrooms, 10 beds, 8 bathrooms
9–14 Aug