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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Home in Kissimmee
Lakefront Villa w/pool 4mi to Walt Disney World
4 bedrooms, 5 beds, 3.5 private bathrooms
28 Jul – 2 Aug
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4.98 out of 5 average rating, 121 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
29 Aug – 3 Sept
New place to stay
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Four Corners
Family Home w/ Pvt Pool & Game Room | Walk to Club
5 bedrooms, 7 beds, 4.5 bathrooms
27 Jul – 1 Aug
New place to stay
Home in Kissimmee
Poolside Heaven in Cumbrian Lakes
4 bedrooms, 6 beds, 3 bathrooms
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
New place to stay
Superhost
Home in Kissimmee
Amazing 6-bedroom home with private spa
6 bedrooms, 6 beds, 5.5 bathrooms
20–25 Aug
New place to stay
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 bedrooms, 9 beds, 4.5 bathrooms
5–10 Jan
5.0 out of 5 average rating, 16 reviews
Home in Kissimmee
Magical Villa with Themed Bedrooms at Reunion
6 bedrooms, 10 beds, 5 bathrooms
27 Jul – 1 Aug
New place to stay
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms, 7 beds, 4.5 bathrooms
10–15 Aug
New place to stay
Superhost
Home in Kissimmee
Magic Palms Villa
6 bedrooms, 9 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Kissimmee
Magic Escape Orlando
4 bedrooms, 6 beds, 3 bathrooms
8–13 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Four Corners
Windsor Westside Cozy 8BR Villa, Lake View, Pool
8 bedrooms, 10 beds, 6 bathrooms
11–16 Aug
New place to stay
Top guest favourite
Home in Kissimmee
NEW! Disney-Themed Escape | Private Pool | Villans
8 bedrooms, 13 beds, 6 bathrooms
9–14 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Townhouse in Kissimmee
5 BD/ 4.5 BA/ Windsor at Westside (2015 MD)
5 bedrooms, 7 beds, 4.5 bathrooms
26–31 Jul
New place to stay
Home in Kissimmee
Chic 8BR All Suites with Pool and Game Room
8 bedrooms, 10 beds, 8 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews