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, 199 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
9–14 Aug
4.91 out of 5 average rating, 93 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds
2–7 Oct
New place to stay
Guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Townhouse in Davenport
Solterra resort townhouse w/ private pool
4 bedrooms, 5 beds
10–15 Oct
New place to stay
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Davenport
Luxury 7-BD Villa - Pool, Theater, and Game Room
7 bedrooms, 14 beds
23–28 Aug
New place to stay
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds
18–23 Oct
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds
3–8 Sept
5.0 out of 5 average rating, 21 reviews
Home in Kissimmee
Disney Area Resort Retreat | Pool, Spa & Mini Golf
3 bedrooms, 7 beds
5–10 Oct
New place to stay
Superhost
Home in Kissimmee
7490 Magic Village 8 guests 4,5 baths 8 min Disney
4 bedrooms, 6 beds
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Kissimmee
2026 NEW 06 Bedrooms at Solara Resort/Private Pool
6 bedrooms, 9 beds
4–9 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds
8–13 Aug
4.96 out of 5 average rating, 49 reviews
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
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds
23–28 Aug
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
2 bedrooms, 3 beds
17–22 Aug
5.0 out of 5 average rating, 4 reviews
Townhouse in Kissimmee
Spacious townhome near Disney w/ patio
4 bedrooms, 6 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds
21–26 Aug
New place to stay