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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, 225 reviews
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
4.9 out of 5 average rating, 104 reviews
Top guest favourite
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
3 bedrooms, 5 beds, 3 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5 bedrooms, 9 beds, 4.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 16 reviews
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
23–28 Jul
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
26–31 Jul
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds, 3 bathrooms
8–13 Aug
4.98 out of 5 average rating, 83 reviews
Superhost
Home in Clermont
Family pool home w/ game room near Disney
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
8–13 Sept
New place to stay
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
New place to stay
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.91 out of 5 average rating, 92 reviews
Home in Kissimmee
Lakefront Charmer 8BR 6BA Home Cinema Pool/Spa
8 bedrooms, 13 beds, 6 bathrooms
26–31 Jul
New place to stay
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4 bedrooms, 6 beds, 4.5 bathrooms
29 Aug – 3 Sept
4.9 out of 5 average rating, 20 reviews
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
4 bedrooms, 8 beds, 5 bathrooms
1–6 Aug
New place to stay
Top guest favourite
Townhouse in Orlando
Fun Family Townhome with Pool and Game Room!
5 bedrooms, 9 beds, 5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews