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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Home in Winter Garden
Downtown Bungalow with fire pit and putting green
2 bedrooms, 2 beds, 1 private bathroom
1–6 Sept
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4.97 out of 5 average rating, 132 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
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
16–21 Aug
Superhost
Home in Kissimmee
Jungle pool home w/ hot tub - close to Disney
New place to stay, 4 bedrooms, 7 beds, 3 bathrooms
17–22 Aug
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
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 5 bathrooms
1–6 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
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
12–17 Oct
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
4.97 out of 5 average rating, 37 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Home in Kissimmee
Magic Palms Villa
5.0 out of 5 average rating, 6 reviews, 6 bedrooms, 9 beds, 3 bathrooms
16–21 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
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
Top guest favourite
Townhouse in Clermont
Family Villa w/ Pool + Games • Near Disney (1189)
4.97 out of 5 average rating, 39 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
19–24 Sept
Superhost
Townhouse in Kissimmee
4 BD/ 3 BA/ Lucaya Village (8-101)
4 bedrooms, 7 beds, 3 bathrooms
16–21 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
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
5.0 out of 5 average rating, 101 reviews, 3 bedrooms, 5 beds, 2 bathrooms
14–19 Aug