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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Home in Kissimmee
3 bedroom Villa in Kissimmee
3 bedrooms, 6 beds, 2 private bathrooms
26 Apr – 1 May
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4.88 out of 5 average rating, 277 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 beds, 5 bathrooms
6–11 Aug
Home in Clermont
Orlando Most Incredible Themed 10BR Villa
New place to stay, 10 bedrooms, 14 beds, 8 bathrooms
14–19 Aug
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds, 4.5 bathrooms
18–23 Oct
Home in Kissimmee
Golden Haven | 14 PPL | Pool | 12 Min to Disney
New place to stay, 5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Aug
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
5.0 out of 5 average rating, 9 reviews, 7 bedrooms, 10 beds, 5.5 bathrooms
31 Dec – 5 Jan
Top guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5.0 out of 5 average rating, 17 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
10–15 Oct
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
New place to stay, 5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Aug
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
6–11 Sept
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5.0 out of 5 average rating, 20 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
3–8 Aug
Superhost
Villa in Clermont
10BR Themed Villa w/ Pool, Theater & Game Room
New place to stay, 10 bedrooms, 14 beds, 8 bathrooms
9–14 Aug
Home in Kissimmee
Modern Disney Villa • 7BR • Private Pool
New place to stay, 7 bedrooms, 9 beds, 6.5 bathrooms
1–6 Aug
Home in Kissimmee
5BR Villa near Disney | Game Room, Pool & Hot Tub
New place to stay, 5 bedrooms, 8 beds, 3.5 bathrooms
3–8 Sept
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
Flat in Kissimmee
3 BD/ 2 BA/ Storey Lake (4741 CD-201)
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Davenport
Home Away from Home + 2 suites
5.0 out of 5 average rating, 7 reviews, 5 bedrooms, 6 beds, 3 bathrooms
21–26 Oct
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
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
New place to stay, 5 bedrooms, 8 beds, 2.5 bathrooms
2–7 Aug
Guest favourite
Home in Kissimmee
Magic Palms Villa
5.0 out of 5 average rating, 6 reviews, 6 bedrooms, 9 beds, 3 bathrooms
13–18 Aug