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Search results; Over 1,000 homes in Kissimmee

Guest favourite
Townhouse in Kissimmee
A Refined Modern Oasis next to Disney World
4 bedrooms, 6 beds, 4.5 private bathrooms
2–7 Aug
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4.94 out of 5 average rating, 129 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
9–14 Nov
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 Aug – 2 Sept
Top guest favourite
Home in Kissimmee
Cozy nd peaceful home w/ lake, near Disney Parks!
3 bedrooms, 4 beds
16–21 Nov
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds
23–28 Aug
Home in Kissimmee
4BR Bright home with private pool
4 bedrooms, 7 beds
11–16 Aug
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
4BR Kissimmee home with private pool
4 bedrooms, 5 beds
17–22 Aug
New place to stay
Guest favourite
Home in Davenport
Home Away from Home + 2 suites
5 bedrooms, 6 beds
21–26 Oct
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds
2–7 Aug
New place to stay
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
8–13 Aug
5.0 out of 5 average rating, 13 reviews
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds
18–23 Oct
Guest favourite
Home in Kissimmee
NEW! Disney-Themed Escape | Private Pool | Villans
8 bedrooms, 13 beds
9–14 Aug
5.0 out of 5 average rating, 5 reviews
Home in Davenport
Upstay Contemporary Retreat w Pool, BBQ & Backyard
5 bedrooms, 7 beds
16–21 Aug
New place to stay
Superhost
Home in Kissimmee
Brand NEW 2026 08 Bedrooms At Solara Resort
8 bedrooms, 11 beds
15–20 Nov
Superhost
Home in Kissimmee
The Most Fun House, Tons of Room and a Huge Pool!
12 bedrooms, 24 beds
5–10 Aug
New place to stay
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds
19–24 Aug
5.0 out of 5 average rating, 20 reviews
Flat in Kissimmee
3BR Townhouse Near Disney Resort Style (8 Guests)
3 bedrooms, 4 beds
1–6 Aug
New place to stay
Guest favourite
Home in Kissimmee
Magic Palms Villa
6 bedrooms, 9 beds
15–20 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
6–11 Sept
5.0 out of 5 average rating, 11 reviews