filters

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
,
4.99 out of 5 average rating, 198 reviews
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
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
Superhost
Home in Kissimmee
Jungle pool home w/ hot tub - close to Disney
New place to stay, 4 bedrooms, 7 beds, 3 bathrooms
17–22 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
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
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
Room in Ocoee
Bedroom and private bathroom
New place to stay, 1 queen bed, 1.5 bathrooms
7–12 Aug
Superhost
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
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 beds, 5 bathrooms
6–11 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
Home in Kissimmee
5BR Villa near Disney | Game Room, Pool & Hot Tub
New place to stay, 5 bedrooms, 8 beds, 3.5 bathrooms
1–6 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
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
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
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
Top guest favourite
Townhouse in Orlando
Fun Family Townhome with Pool and Game Room!
5.0 out of 5 average rating, 8 reviews, 5 bedrooms, 9 beds, 5 bathrooms
23–28 Aug
Superhost
Home in Kissimmee
Resort Living | 4BR/3BA | Paradise Palms
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
Home in Kissimmee
Sleeps 13-Park Shuttle-Themed Rooms-Solara Resort
New place to stay, 5 bedrooms, 8 beds, 5.5 bathrooms
1–6 Aug