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Search results; Over 1,000 homes in Kissimmee

Superhost
Apartment in Kissimmee
H-Gated Resort-5 miles to Disney-2 FREE Water Park
2 bedrooms, 4 beds, 2 private bathrooms
11–16 Aug
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4.81 out of 5 average rating, 206 reviews
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 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
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
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
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
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
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Lucaya Village (8-101)
4 bedrooms, 7 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 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 Kissimmee
4BR Kissimmee home with private pool
4 bedrooms, 5 beds, 2 bathrooms
17–22 Aug
New place to stay
Home in Davenport
Upstay Contemporary Retreat w Pool, BBQ & Backyard
5 bedrooms, 7 beds, 4 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
3 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 37 reviews
Guest favourite
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Storey Lake (4285 Qs)
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 6 reviews
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
5 bedrooms, 7 beds, 4 bathrooms
3–8 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Davenport
The Ultimate Family Getaway Near Disney
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Aug
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 5 reviews