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 Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 93 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
2–7 Aug
New place to stay
Flat in Clermont
The Nest-Lake Sumner
1 queen bed, 1 bathroom
9–14 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
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
9–14 Nov
5.0 out of 5 average rating, 3 reviews
Flat in Clermont
Cozy 4 U-Lake Sumner
1 bedroom, 1 queen bed, 1 bathroom
8–13 Aug
New place to stay
Superhost
Home in Clermont
Pool, hot tub & arcade - 19 mins to Disney
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
28 Aug – 2 Sept
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
New place to stay
Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds, 5.5 bathrooms
23–28 Aug
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
5.0 out of 5 average rating, 14 reviews
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Flat in Kissimmee
Magical Getaway: 2-BR Near Disney
2 bedrooms, 3 beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
3–8 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
4.98 out of 5 average rating, 86 reviews
Guest favourite
Home in Kissimmee
NEW! Disney-Themed Escape | Private Pool | Villans
8 bedrooms, 13 beds, 6 bathrooms
9–14 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Kissimmee
Greek Villa w/ Sunny Pool just 20 Min to Disney
4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
New place to stay