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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
,
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
10–15 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
6–11 Mar
5.0 out of 5 average rating, 8 reviews
Home in Clermont
Cozy Mod Escape |Sleeps 7| "Oak Tree House"
3 bedrooms, 5 beds, 2 bathrooms
17–22 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
19–24 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
6 bedrooms, 10 beds, 4 bathrooms
12–17 Jul
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
4 bedrooms, 8 beds, 5 bathrooms
12–17 Jul
New place to stay
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, 16 reviews
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
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
15–20 Aug
New place to stay
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, 3 reviews
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
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
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 24 reviews
Superhost
Home in Clermont
Brand NEW 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4 bathrooms
16–21 Sept
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
15–20 Jul
4.89 out of 5 average rating, 55 reviews
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
1 bed, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 bathrooms
26–31 Jul
4.98 out of 5 average rating, 48 reviews