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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
5–10 Aug
4.91 out of 5 average rating, 93 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
1–6 Aug
5.0 out of 5 average rating, 11 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed
1–6 Aug
New place to stay
Room in Ocoee
Bedroom and private bathroom
1 queen bed
7–12 Aug
New place to stay
Apartment in Kissimmee
*NEW* 3BR/2BA Condo w/ pool, steps to Disney
3 bedrooms, 4 beds
1–6 Aug
New place to stay
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds
1–6 Aug
4.89 out of 5 average rating, 56 reviews
Flat in Kissimmee
Family Vacation Condo with pool/20 Min from Disney
2 bedrooms, 4 beds
7–12 Aug
New place to stay
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms, 7 beds
16–21 Aug
New place to stay
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
1 bed
1–6 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed
1–6 Aug
4.97 out of 5 average rating, 38 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds
31 Aug – 5 Sept
New place to stay
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
8–13 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Kissimmee
Brand New Designer Townhome | 10 Min to Disney
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 25 reviews
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Villa in Clermont
Villa near Disney with complimentary spa heating!
4 bedrooms, 6 beds
11–16 Aug
4.83 out of 5 average rating, 12 reviews
Home in Davenport
Modern 4BR w/ Private Pool - Minutes from Disney
4 bedrooms, 6 beds
8–13 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds
3–8 Aug
5.0 out of 5 average rating, 27 reviews
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds
9–14 Aug
New place to stay