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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 Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
31 Aug – 5 Sept
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
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
6–11 Aug
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 Kissimmee
Sleeps 13-Park Shuttle-Themed Rooms-Solara Resort
5 bedrooms, 8 beds, 5.5 bathrooms
1–6 Aug
New place to stay
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
5.0 out of 5 average rating, 13 reviews
Home in Four Corners
The Epic Escape Mansion 9Br near Disney/Universal
9 bedrooms, 20 beds, 5 bathrooms
9–14 Aug
New place to stay
Superhost
Villa in Clermont
10BR Themed Villa w/ Pool, Theater & Game Room
10 bedrooms, 14 beds, 8 bathrooms
9–14 Aug
New place to stay
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5 bedrooms, 7 beds, 5.5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 20 reviews
Guest favourite
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
9–14 Nov
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
31 Dec – 5 Jan
5.0 out of 5 average rating, 9 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, 38 reviews
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
New place to stay
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 102 reviews
Superhost
Home in Clermont
Hidden Springs retreat w/ pool, spa & game room
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 reviews
Home in Kissimmee
5BR Villa near Disney | Game Room, Pool & Hot Tub
5 bedrooms, 8 beds, 3.5 bathrooms
3–8 Sept
New place to stay
Superhost
Townhouse in Davenport
Luxury Stay 5BR at Windsor Island - Near Disney
5 bedrooms, 7 beds, 5.5 bathrooms
30 Aug – 4 Sept