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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Cottage in Winter Garden
The Heart of Winter Garden: Walk to shops & dining
2 bedrooms, 2 beds, 1 private bathroom
9–14 Sept
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4.99 out of 5 average rating, 198 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 93 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
New place to stay, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Room in Ocoee
Bedroom and private bathroom
New place to stay, 1 queen bed, 1.5 bathrooms
7–12 Aug
Apartment in Kissimmee
*NEW* 3BR/2BA Condo w/ pool, steps to Disney
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
5.0 out of 5 average rating, 4 reviews, 1 bed, 1 bathroom
1–6 Aug
Flat in Kissimmee
Family Vacation Condo with pool/20 Min from Disney
New place to stay, 2 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
Top guest favourite
Townhouse in Clermont
The gold cottage
4.89 out of 5 average rating, 56 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
New place to stay, 5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Aug
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
4.97 out of 5 average rating, 38 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
New place to stay, 10 bedrooms, 16 beds, 8 bathrooms
31 Aug – 5 Sept
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
Top guest favourite
Home in Kissimmee
Brand New Designer Townhome | 10 Min to Disney
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
New place to stay, 4 bedrooms, 8 beds, 3.5 bathrooms
9–14 Aug
Guest favourite
Villa in Clermont
Villa near Disney with complimentary spa heating!
4.83 out of 5 average rating, 12 reviews, 4 bedrooms, 6 beds, 2 bathrooms
11–16 Aug
Home in Four Corners
The Epic Escape Mansion 9Br near Disney/Universal
New place to stay, 9 bedrooms, 20 beds, 5 bathrooms
9–14 Aug
Home in Davenport
Modern 4BR w/ Private Pool - Minutes from Disney
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 3 bathrooms
8–13 Aug