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Search results; Over 1,000 homes in Kissimmee

Top guest favourite
Apartment in Kissimmee
Luxury 3 Bed/2 Bath Condo 4 miles from WDW
3 bedrooms, 4 beds, 2 private bathrooms
3–8 Aug
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4.88 out of 5 average rating, 130 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
28 Aug – 2 Sept
Home in Davenport
Upstay Contemporary Retreat w Pool, BBQ & Backyard
5 bedrooms, 7 beds, 4 bathrooms
16–21 Aug
New place to stay
Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds, 5.5 bathrooms
23–28 Aug
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
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
14–19 Feb
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds, 2.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Davenport
Home Away from Home + 2 suites
5 bedrooms, 6 beds, 3 bathrooms
21–26 Oct
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Kissimmee
Brand NEW 2026 08 Bedrooms At Solara Resort
8 bedrooms, 11 beds, 6.5 bathrooms
15–20 Nov
Home in Kissimmee
Golden Haven | Heater Pool | 5 Beds | Near Disney
5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
5.0 out of 5 average rating, 14 reviews
Villa in Kissimmee
Serenity Palms | 9BR Charming Home Near Disney
9 bedrooms, 12 beds, 8.5 bathrooms
9–14 Aug
Home in Kissimmee
Woodland Oasis: Brand-new Home 15 Min to Disney
3 bedrooms, 6 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Davenport
Heated Pool + Movie Room | Champions Gate | 5BD
5 bedrooms, 9 beds, 4.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Kissimmee
The Most Fun House, Tons of Room and a Huge Pool!
12 bedrooms, 24 beds, 15 bathrooms
5–10 Aug
New place to stay
Flat in Kissimmee
Vacation Condo with pool-20 Min from Disney
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Kissimmee
Magic Palms Villa
6 bedrooms, 9 beds, 3 bathrooms
14–19 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Kissimmee
8 Bedrooms/ 5 Bathrooms/ Storey Lake (4582NL)
8 bedrooms, 12 beds, 5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Lucaya Village (8-101)
4 bedrooms, 7 beds, 3 bathrooms
30 Aug – 4 Sept