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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds, 1 private bathroom
3–8 Aug
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4.9 out of 5 average rating, 105 reviews
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
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 93 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
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
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 beds, 5 bathrooms
28 Aug – 2 Sept
Home in Kissimmee
Sleeps 13-Park Shuttle-Themed Rooms-Solara Resort
New place to stay, 5 bedrooms, 8 beds, 5.5 bathrooms
1–6 Aug
Home in Four Corners
The Epic Escape Mansion 9Br near Disney/Universal
New place to stay, 9 bedrooms, 20 beds, 5 bathrooms
9–14 Aug
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
20–25 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
Amazing Themed 07 Bedrooms at Solara Resort
5.0 out of 5 average rating, 9 reviews, 7 bedrooms, 10 beds, 5.5 bathrooms
31 Dec – 5 Jan
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
29 Aug – 3 Sept
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
5.0 out of 5 average rating, 102 reviews, 3 bedrooms, 5 beds, 2 bathrooms
14–19 Aug
Superhost
Villa in Clermont
10BR Themed Villa w/ Pool, Theater & Game Room
New place to stay, 10 bedrooms, 14 beds, 8 bathrooms
16–21 Aug
Guest favourite
Villa in Clermont
Villa near Disney with complimentary spa heating!
4.83 out of 5 average rating, 12 reviews, 4 bedrooms, 6 beds, 2 bathrooms
11–16 Aug
Home in Kissimmee
5BR Villa near Disney | Game Room, Pool & Hot Tub
New place to stay, 5 bedrooms, 8 beds, 3.5 bathrooms
3–8 Sept
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
Home in Ocoee
Serenity Retreat
New place to stay, 2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
10–15 Aug