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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds, 1 private bathroom
3–8 Aug
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4.9 out of 5 average rating, 105 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
New place to stay, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 93 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
New place to stay, 7 bedrooms, 6 beds, 4.5 bathrooms
21–26 Sept
Superhost
Home in Davenport
In Resort Themed Home /Pvt Pool / Game room 273961
5 bedrooms, 7 beds, 5.5 bathrooms
21–26 Aug
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
5.0 out of 5 average rating, 26 reviews, 4 bedrooms, 6 beds, 3 bathrooms
2–7 Aug
Home in Kissimmee
Marvelous place to relax, w/ pool, near all parks!
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Nov
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
Superhost
Home in Kissimmee
Magic Palms Villa
5.0 out of 5 average rating, 5 reviews, 6 bedrooms, 9 beds, 3 bathrooms
16–21 Aug
Guest favourite
Villa in Clermont
Villa near Disney with complimentary spa heating!
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
4.97 out of 5 average rating, 37 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Superhost
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5.0 out of 5 average rating, 4 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
31 Aug – 5 Sept
Top guest favourite
Townhouse in Orlando
Fun Family Townhome with Pool and Game Room!
5.0 out of 5 average rating, 7 reviews, 5 bedrooms, 9 beds, 5 bathrooms
23–28 Aug
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Superhost
Home in Clermont
Family pool home w/ game room near Disney
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Townhouse in Clermont
The gold cottage
4.89 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Superhost
Flat in Kissimmee
3 BD/ 2 BA/ Windsor Palms Resort (2305-205)
3 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
16–21 Aug