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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
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
21–26 Sept
New place to stay
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
4 bedrooms, 5 beds, 3 bathrooms
9–14 Aug
New place to stay
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
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
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
Home in Clermont
5-Star Experience near Disney with Pool
5 bedrooms, 8 beds, 4 bathrooms
17–22 Aug
5.0 out of 5 average rating, 3 reviews
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 Orlando
Brand-new 5BR Paradiso Minecraft adventure villa
5 bedrooms, 9 beds, 5 bathrooms
1–6 Aug
New place to stay
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
12–17 Oct
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, 7 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
Magic Palms Villa
6 bedrooms, 9 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Four Corners
Family Home w/ Pvt Pool & Game Room | Walk to Club
5 bedrooms, 7 beds, 4.5 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 26 reviews
Superhost
Villa in Clermont
10BR Themed Villa w/ Pool, Theater & Game Room
10 bedrooms, 14 beds, 8 bathrooms
3–8 Aug
New place to stay
Superhost
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Clermont
Family pool home w/ game room near Disney
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5 bedrooms, 9 beds, 4.5 bathrooms
12–17 Feb
5.0 out of 5 average rating, 16 reviews