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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
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 95 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
Guest favourite
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds, 6 bathrooms
23–28 Aug
New place to stay
Guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
4.98 out of 5 average rating, 87 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
2–7 Oct
New place to stay
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
New place to stay
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Lucaya Village (8-101)
4 bedrooms, 7 beds, 3 bathrooms
30 Aug – 4 Sept
Top guest favourite
Flat in Kissimmee
Magical Getaway: 2-BR Near Disney
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds, 5.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 bathrooms
21–26 Aug
4.98 out of 5 average rating, 51 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Kissimmee
Luxury Villa Near Parks | Private Pool & Game Room
5 bedrooms, 5 beds, 4 bathrooms
24–29 Aug
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 12 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Home in Clermont
Orlando Most Incredible Themed 10BR Villa
10 bedrooms, 14 beds, 8 bathrooms
30 Aug – 4 Sept
New place to stay