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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, 225 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
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
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
31 Aug – 5 Sept
New place to stay
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
28 Aug – 2 Sept
Home in Davenport
Upstay Contemporary Retreat w Pool, BBQ & Backyard
5 bedrooms, 7 beds, 4 bathrooms
16–21 Aug
New place to stay
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
Flat in Kissimmee
Family Vacation Condo with pool/20 Min from Disney
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
New place to stay
Room in Ocoee
Bedroom and private bathroom
1 queen bed, 1.5 bathrooms
7–12 Aug
New place to stay
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
1–6 Aug
4.97 out of 5 average rating, 38 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 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
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
New place to stay
Top guest favourite
Home in Kissimmee
Brand New Designer Townhome | 10 Min to Disney
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 26 reviews
Apartment in Kissimmee
*NEW* 3BR/2BA Condo w/ pool, steps to Disney
3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
New place to stay
Superhost
Home in Kissimmee
The Most Fun House, Tons of Room and a Huge Pool!
12 bedrooms, 24 beds, 15 bathrooms
5–10 Aug
New place to stay
Home in Kissimmee
The Magical Wizard's Hideaway
4 bedrooms, 6 beds, 4 bathrooms
2–7 Aug
New place to stay
Townhouse in Davenport
Beautiful townhouse just 15 minutes from Disney
4 bedrooms, 5 beds, 3 bathrooms
15–20 Aug
New place to stay