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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
21–26 Sept
New place to stay
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
4 bedrooms, 5 beds
9–14 Aug
New place to stay
Superhost
Home in Davenport
In Resort Themed Home /Pvt Pool / Game room 273961
5 bedrooms, 7 beds
21–26 Aug
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
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
8–13 Aug
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Orlando
Brand-new 5BR Paradiso Minecraft adventure villa
5 bedrooms, 9 beds
1–6 Aug
New place to stay
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds
12–17 Oct
New place to stay
Superhost
Home in Kissimmee
Magic Palms Villa
6 bedrooms, 9 beds
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds
20–25 Sept
Top guest favourite
Townhouse in Orlando
Fun Family Townhome with Pool and Game Room!
5 bedrooms, 9 beds
23–28 Aug
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Four Corners
Family Home w/ Pvt Pool & Game Room | Walk to Club
5 bedrooms, 7 beds
9–14 Aug
New place to stay
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds
2–7 Aug
5.0 out of 5 average rating, 26 reviews
Superhost
Flat in Kissimmee
3 BD/ 2 BA/ Windsor Palms Resort (2305-205)
3 bedrooms, 4 beds
5–10 Aug
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
1–6 Aug
4.91 out of 5 average rating, 93 reviews
Superhost
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms, 7 beds
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
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Townhouse in Kissimmee
Disney Theme Rooms | Private Pool | Storey Lake
4 bedrooms, 6 beds
26–31 Aug
5.0 out of 5 average rating, 36 reviews
Superhost
Home in Kissimmee
Emerald Island Resort - 3 Miles from Disneyland!
3 bedrooms, 4 beds
1–6 Aug
New place to stay