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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
Top guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
2 bedrooms, 3 beds
14–19 Jul
4.99 out of 5 average rating, 116 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds
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
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
17–22 Jul
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
4 bedrooms, 8 beds
12–17 Jul
New place to stay
Guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
6 bedrooms, 10 beds
12–17 Jul
5.0 out of 5 average rating, 6 reviews
Home in Kissimmee
Magic-Ready 4BR Pool Home Near Disney
4 bedrooms, 6 beds
19–24 Jul
New place to stay
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
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
26–31 Jul
5.0 out of 5 average rating, 16 reviews
Superhost
Home in Clermont
Family pool home w/ game room near Disney
4 bedrooms, 5 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds
15–20 Aug
New place to stay
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
19–24 Jul
4.91 out of 5 average rating, 92 reviews
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds
6–11 Sept
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds
20–25 Sept
Superhost
Home in Clermont
Brand NEW 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds
16–21 Sept
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds
9–14 Aug
5.0 out of 5 average rating, 8 reviews
Townhouse in Kissimmee
Spacious townhome near Disney w/ patio
4 bedrooms, 6 beds
15–20 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds
26–31 Jul
4.98 out of 5 average rating, 48 reviews