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Search results; Over 1,000 homes in Winter Garden

Descriptions are based on details hosts provide
Guest favourite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
,
4.92 out of 5 average rating, 224 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
30 Jul – 4 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
4.89 out of 5 average rating, 55 reviews
Top guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
6 bedrooms, 10 beds, 4 bathrooms
19–24 Jul
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
31 Jul – 5 Aug
New place to stay
Top guest favourite
Home in Clermont
Lake views and a deck near downtown
3 bedrooms, 5 beds, 2 bathrooms
23–28 Jul
5.0 out of 5 average rating, 11 reviews
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Superhost
Home in Clermont
Brand-new home 8 miles from Disney
10 bedrooms, 16 beds, 8 bathrooms
15–20 Aug
New place to stay
Superhost
Home in Clermont
Pool, hot tub, and game room near Disney
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Orlando
25 minutes from Disney, private backyard
3 bedrooms, 4 beds, 4 bathrooms
19–24 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds, 3 bathrooms
29 Jul – 3 Aug
4.98 out of 5 average rating, 83 reviews
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
New place to stay
Top guest favourite
Townhouse in Kissimmee
4.3 miles from Disney with a pool
3 bedrooms, 5 beds, 3 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Ocoee
Lakefront with a beach and fire pit
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.91 out of 5 average rating, 92 reviews
Superhost
Home in Kissimmee
Beautiful 4 Bedroom Villa – Near Disney Parks
4 bedrooms, 6 beds, 4.5 bathrooms
18–23 Jul
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.99 out of 5 average rating, 78 reviews
Top guest favourite
Home in Clermont
Private pool, spa, and game room
6 bedrooms, 9 beds, 4 bathrooms
26–31 Jul
4.98 out of 5 average rating, 48 reviews
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Guest favourite
Home in Clermont
Gated resort with pool near Disney
5 bedrooms, 7 beds, 5.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 17 reviews