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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
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Home in Clermont
Orlando Most Incredible Themed 10BR Villa
New place to stay, 10 bedrooms, 14 beds, 8 bathrooms
14–19 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
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
31 Aug – 5 Sept
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
4.97 out of 5 average rating, 38 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 6 beds, 5 bathrooms
16–21 Aug
Superhost
Home in Clermont
Hidden Springs retreat w/ pool, spa & game room
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
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
11–16 Aug
Home in Kissimmee
Golden Haven | 14 PPL | Pool | 12 Min to Disney
New place to stay, 5 bedrooms, 7 beds, 4.5 bathrooms
9–14 Aug
Home in Kissimmee
5BR Villa near Disney | Game Room, Pool & Hot Tub
New place to stay, 5 bedrooms, 8 beds, 3.5 bathrooms
1–6 Aug
Top guest favourite
Home in Kissimmee
Brand New Designer Townhome | 10 Min to Disney
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
Guest favourite
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
10–15 Oct
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
New place to stay, 4 bedrooms, 8 beds, 5 bathrooms
2–7 Aug
Superhost
Townhouse in Four Corners
Gorgeous Villa w/ Mickey Room, Private Pool & More
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
Superhost
Home in Four Corners
10 BD/ 8 BA/ Windsor Cay (1017 BP)
5.0 out of 5 average rating, 3 reviews, 10 bedrooms, 15 beds, 8 bathrooms
16–21 Aug