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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Guest suite in Winter Garden
Designer Guest Suite Near Disney/Universal/DT
1 bedroom, 3 beds, 1 private bathroom
2–7 Aug
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4.84 out of 5 average rating, 413 reviews
Home in Clermont
Orlando Most Incredible Themed 10BR Villa
10 bedrooms, 14 beds, 8 bathrooms
14–19 Aug
New place to stay
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
Home in Kissimmee
Golden Haven | 14 PPL | Pool | 12 Min to Disney
5 bedrooms, 7 beds, 4.5 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
4.91 out of 5 average rating, 93 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
Home in Clermont
5-Star Experience near Disney with Pool
5 bedrooms, 8 beds, 4 bathrooms
17–22 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
4 bedrooms, 8 beds, 5 bathrooms
1–6 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
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 4 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 Kissimmee
Jungle pool home w/ hot tub - close to Disney
4 bedrooms, 7 beds, 3 bathrooms
17–22 Aug
New place to stay
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 Kissimmee
4 BD/ 3 BA/ Lucaya Village (8-101)
4 bedrooms, 7 beds, 3 bathrooms
16–21 Aug
Superhost
Home in Clermont
Hidden Springs retreat w/ pool, spa & game room
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Villa in Clermont
10BR Themed Villa w/ Pool, Theater & Game Room
10 bedrooms, 14 beds, 8 bathrooms
9–14 Aug
New place to stay
Superhost
Home in Kissimmee
Emerald Island Resort - 3 Miles from Disneyland!
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
New place to stay
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, 4 reviews
Superhost
Home in Four Corners
Windsor Westside Dreamy 8BR Villa, Private Pool
8 bedrooms, 10 beds, 6 bathrooms
9–14 Aug
New place to stay