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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds, 1 private bathroom
3–8 Aug
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4.9 out of 5 average rating, 105 reviews
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
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
1–6 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
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
Guest favourite
Villa in Clermont
Villa near Disney with complimentary spa heating!
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 6 beds, 2 bathrooms
11–16 Aug
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
New place to stay, 4 bedrooms, 8 beds, 5 bathrooms
2–7 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 Clermont
Sunset Paradise Villa in Orlando, Disney area.
5.0 out of 5 average rating, 27 reviews, 4 bedrooms, 6 beds, 3 bathrooms
3–8 Aug
Superhost
Townhouse in Four Corners
Gorgeous Villa w/ Mickey Room, Private Pool & More
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
Home in Four Corners
The Epic Escape Mansion 9Br near Disney/Universal
New place to stay, 9 bedrooms, 20 beds, 5 bathrooms
2–7 Aug
Top guest favourite
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 6 beds, 5 bathrooms
16–21 Aug
Superhost
Townhouse in Kissimmee
4 BD/ 3 BA/ Lucaya Village (8-101)
4 bedrooms, 7 beds, 3 bathrooms
16–21 Aug
Guest favourite
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
9–14 Nov
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
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 Davenport
Luxury Stay 5BR at Windsor Island - Near Disney
5 bedrooms, 7 beds, 5.5 bathrooms
30 Aug – 4 Sept
Townhouse in Davenport
Beautiful townhouse just 15 minutes from Disney
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
1–6 Sept
Top guest favourite
Townhouse in Clermont
The gold cottage
4.89 out of 5 average rating, 55 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug