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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Home in Winter Garden
Downtown Bungalow with fire pit and putting green
2 bedrooms, 2 beds, 1 private bathroom
1–6 Sept
,
4.97 out of 5 average rating, 131 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds
30 Sept – 5 Oct
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
5–10 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds
3–8 Aug
4.9 out of 5 average rating, 104 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds
8–13 Sept
New place to stay
Top guest favourite
Home in Clermont
Lux 6 bed with Pool/SPA
6 bedrooms, 10 beds
19–24 Jul
5.0 out of 5 average rating, 8 reviews
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
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds
25–30 Aug
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds
2–7 Aug
5.0 out of 5 average rating, 25 reviews
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds
20–25 Sept
Guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5 bedrooms, 9 beds
21–26 Aug
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, 4 reviews
Superhost
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
3 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4 bedrooms, 6 beds
29 Aug – 3 Sept
4.9 out of 5 average rating, 20 reviews
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
Guest favourite
Home in Clermont
2026 NEW Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 8 beds
11–16 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds
8–13 Aug
4.98 out of 5 average rating, 83 reviews
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds
6–11 Sept
Top guest favourite
Flat in Kissimmee
Amazing 03 Bedrooms/ 03 Baths / Sleeps 08
3 bedrooms, 5 beds
25–30 Aug
4.97 out of 5 average rating, 36 reviews