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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Guest suite in Winter Garden
Private In-Law Suite Near Disney/Universal/DT
1 bedroom, 1 bed, 1 private bathroom
22–27 Aug
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4.84 out of 5 average rating, 425 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
9–14 Aug
4.91 out of 5 average rating, 93 reviews
Top guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
9–14 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 14 reviews
Superhost
Home in Clermont
Game room + pool home near Orlando's top parks
4 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds
23–28 Aug
4.98 out of 5 average rating, 86 reviews
Home in Clermont
New! Windsor Cay Resort | Private Pool | 5BR/5.5BA
5 bedrooms, 6 beds
16–21 Aug
New place to stay
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
2 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds
18–23 Oct
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms, 7 beds
16–21 Aug
New place to stay
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds
3–8 Sept
5.0 out of 5 average rating, 21 reviews
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds
21–26 Aug
New place to stay
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds
23–28 Aug
Top guest favourite
Home in Orlando
Walk to Epic Universe | New! 3BR/3.5BA | Vista cay
3 bedrooms, 5 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
10–15 Aug
New place to stay
Townhouse in Davenport
Beautiful townhouse just 15 minutes from Disney
4 bedrooms, 5 beds
16–21 Aug
New place to stay
Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds
23–28 Aug