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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
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4.97 out of 5 average rating, 132 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
New place to stay
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
4.91 out of 5 average rating, 93 reviews
Top guest favourite
Townhouse in Kissimmee
3 BD/ 2.5 BA/ Encantada Resort (3113 YL)
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.89 out of 5 average rating, 56 reviews
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds, 3.5 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
4.96 out of 5 average rating, 49 reviews
Superhost
Home in Clermont
Pool, hot tub & arcade - 19 mins to Disney
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
4.98 out of 5 average rating, 86 reviews
Guest favourite
Home in Davenport
LuxTownhouse Just min from DisneyWorld & Universal
4 bedrooms, 6 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Clermont
Family Fun House at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Four Corners
Gorgeous Villa w/ Mickey Room, Private Pool & More
4 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Clermont
2026 Cozy Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4 bathrooms
22–27 Sept
5.0 out of 5 average rating, 24 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
9–14 Nov
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
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
3–8 Aug
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Davenport
Luxury Disney Villa | Pool | Arcade | King Suites
4 bedrooms, 6 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 5 reviews