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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Home in Winter Garden
Downtown Winter Garden, Florida
2 bedrooms, 2 beds, 1 private bathroom
1–6 Sept
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4.99 out of 5 average rating, 159 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
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
4 bedrooms, 5 beds, 3 bathrooms
16–21 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
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
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 Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
20–25 Nov
New place to stay
Superhost
Home in Clermont
Hidden Springs retreat w/ pool, spa & game room
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Kissimmee
Magic Palms Villa
6 bedrooms, 9 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
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, 37 reviews
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 4 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
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, 7 reviews
Guest favourite
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, 5 reviews
Superhost
Townhouse in Davenport
Luxury Stay 5BR at Windsor Island - Near Disney
5 bedrooms, 7 beds, 5.5 bathrooms
30 Aug – 4 Sept
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
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
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Four Corners
10 BD/ 8 BA/ Windsor Cay (1017 BP)
10 bedrooms, 15 beds, 8 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 reviews