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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
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 91 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
Top guest favourite
Guest house in Winter Garden
A place with a view
4.9 out of 5 average rating, 104 reviews, 2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
Top guest favourite
Villa in Clermont
Villa for 5 - Visiting family, Golfing, Downtown
4.96 out of 5 average rating, 47 reviews, 2 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
Villa in Orlando
Charming Orlando Villa with Pool & Family Fun
New place to stay, 4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
Superhost
Flat in Kissimmee
Comfortable 3BR Apt at Club Cortile Near Disney
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
Home in Kissimmee
Santosh Cove Retreat
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
4–9 Sept
Top guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
4.99 out of 5 average rating, 116 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
Superhost
Townhouse in Kissimmee
4 BD/ 3 BA/ West Lucaya (8984 SP)
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 3 bathrooms
16–21 Aug
Superhost
Cottage in Kissimmee
Beauty and the Beast
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Kissimmee
Brand New Designer Townhome | 10 Min to Disney
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
Superhost
Townhouse in Four Corners
Gorgeous Villa w/ Mickey Room, Private Pool & More
New place to stay, 4 bedrooms, 8 beds, 3 bathrooms
18–23 Jul
Superhost
Home in Clermont
Brand NEW 10 BRD/Pool/Game Room At Windsor Cay
5.0 out of 5 average rating, 5 reviews, 10 bedrooms, 15 beds, 7 bathrooms
20–25 Sept
Townhouse in Kissimmee
4 Suites, Private Jacuzzi & Prime Location
New place to stay, 4 bedrooms, 5 beds, 4.5 bathrooms
12–17 Jul
Apartment in Kissimmee
Stay Tropical At Caribe Cove
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 5 beds, 2 bathrooms
17–22 Jul
Townhouse in Kissimmee
Disney, Resort Style, 4 BDRM, Sleeps 8, 3 Bath
4 bedrooms, 6 beds, 3 bathrooms
25–30 Oct
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
15–20 Aug
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4.88 out of 5 average rating, 17 reviews, 4 bedrooms, 6 beds, 4.5 bathrooms
16–21 Aug
Guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5.0 out of 5 average rating, 13 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
27 Sept – 2 Oct