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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Home in Winter Garden
Downtown Winter Garden, Florida
2 bedrooms, 2 beds, 1 private bathroom
1–6 Sept
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4.99 out of 5 average rating, 159 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 94 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
Home in Kissimmee
Premium house, 4 bedrooms, sleeps 10, Kissimme
4 bedrooms, 8 beds, 3 bathrooms
24–29 Aug
New place to stay
Superhost
Home in Four Corners
2026 BRAND NEW 08BD At Windsor Cay
8 bedrooms, 8 beds, 6 bathrooms
15–20 Aug
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
3–8 Sept
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 28 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Aug
New place to stay
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Superhost
Place to stay in Gotha
Private Room • Exclusive Bathroom • MCO & Disney
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
New place to stay
Superhost
Home in Kissimmee
7490 Magic Village 8 guests 4,5 baths 8 min Disney
4 bedrooms, 6 beds, 4.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 3 reviews
Flat in Clermont
Cozy 4 U-Lake Sumner
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
New place to stay
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 12 reviews
Home in Kissimmee
4BR Kissimmee home with private pool
4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
23–28 Nov
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 bathrooms
21–26 Aug
4.98 out of 5 average rating, 51 reviews
Superhost
Home in Gotha
Stylish Home • Sleeps 8 • Near Disney & Universal
3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Aug
New place to stay