filters

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
,
4.9 out of 5 average rating, 105 reviews
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
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
9–14 Aug
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
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
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 Orlando
Brand-new 5BR Paradiso Minecraft adventure villa
New place to stay, 5 bedrooms, 9 beds, 5 bathrooms
1–6 Aug
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
12–17 Oct
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
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 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
Home in Four Corners
Family Home w/ Pvt Pool & Game Room | Walk to Club
New place to stay, 5 bedrooms, 7 beds, 4.5 bathrooms
9–14 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
Superhost
Flat in Kissimmee
3 BD/ 2 BA/ Windsor Palms Resort (2305-205)
3 bedrooms, 4 beds, 2 bathrooms
5–10 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
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
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 Kissimmee
Disney Theme Rooms | Private Pool | Storey Lake
5.0 out of 5 average rating, 36 reviews, 4 bedrooms, 6 beds, 3 bathrooms
26–31 Aug
Superhost
Home in Kissimmee
Emerald Island Resort - 3 Miles from Disneyland!
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug