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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Guest suite in Winter Garden
Private In-Law Suite Near Disney/Universal/DT
1 bedroom, 1 bed, 1 private bathroom
22–27 Aug
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4.84 out of 5 average rating, 422 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
4.91 out of 5 average rating, 93 reviews
Superhost
Home in Kissimmee
Jungle pool home w/ hot tub - close to Disney
4 bedrooms, 7 beds, 3 bathrooms
17–22 Aug
New place to stay
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
New place to stay
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
31 Aug – 5 Sept
New place to stay
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, 13 reviews
Room in Ocoee
Bedroom and private bathroom
1 queen bed, 1.5 bathrooms
7–12 Aug
New place to stay
Superhost
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
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
6–11 Aug
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
1–6 Aug
4.97 out of 5 average rating, 38 reviews
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
4 bedrooms, 8 beds, 5 bathrooms
2–7 Aug
New place to stay
Guest favourite
Villa in Clermont
Villa near Disney with complimentary spa heating!
4 bedrooms, 6 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Kissimmee
Brand New Designer Townhome | 10 Min to Disney
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 25 reviews
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
Resort Living | 4BR/3BA | Paradise Palms
4 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
New place to stay
Top guest favourite
Townhouse in Orlando
Fun Family Townhome with Pool and Game Room!
5 bedrooms, 9 beds, 5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
31 Dec – 5 Jan
5.0 out of 5 average rating, 9 reviews
Home in Kissimmee
Sleeps 13-Park Shuttle-Themed Rooms-Solara Resort
5 bedrooms, 8 beds, 5.5 bathrooms
1–6 Aug
New place to stay