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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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4.92 out of 5 average rating, 224 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5.0 out of 5 average rating, 7 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
21–26 Sept
Top guest favourite
Townhouse in Clermont
The gold cottage
4.89 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
8–13 Sept
Top guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
5.0 out of 5 average rating, 7 reviews, 6 bedrooms, 10 beds, 4 bathrooms
19–24 Jul
Superhost
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
3–8 Aug
Home in Kissimmee
Magic-Ready 4BR Pool Home Near Disney
New place to stay, 4 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Superhost
Home in Clermont
Family pool home w/ game room near Disney
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 5 beds, 3 bathrooms
28 Jul – 2 Aug
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Guest favourite
Home in Clermont
5 BD/ 5.5 BA/ Windsor Cay (15839 CC)
5.0 out of 5 average rating, 18 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
26–31 Jul
Superhost
Home in Kissimmee
Greek Villa w/ Sunny Pool just 20 Min to Disney
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 92 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4.9 out of 5 average rating, 20 reviews, 4 bedrooms, 6 beds, 4.5 bathrooms
16–21 Aug
Superhost
Home in Kissimmee
Beautiful 4 Bedroom Villa – Near Disney Parks
4 bedrooms, 6 beds, 4.5 bathrooms
18–23 Jul
Home in Davenport
Davenport Disney Destination w/Pool
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
Superhost
Home in Orlando
Themed 5BR Villa Minutes from Disney & Universal
5 bedrooms, 7 beds, 5 bathrooms
1–6 Sept
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept