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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Flat in Winter Garden
Stay A While
1 bedroom, 3 beds, 1 private bathroom
5–10 Aug
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4.89 out of 5 average rating, 169 reviews
Superhost
Place to stay in Oakland
Oakland Trails
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
4.91 out of 5 average rating, 92 reviews
Superhost
Cottage in Kissimmee
Beauty and the Beast
2 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 3 reviews
Flat in Kissimmee
Family Orlando Condo Resort near Disney
3 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
New place to stay
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
30 Jul – 4 Aug
5.0 out of 5 average rating, 7 reviews
Flat in Orlando
King Suite w Pool & Hot Tub Near Disney
1 bedroom, 2 beds, 1 bathroom
11–16 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
4.96 out of 5 average rating, 48 reviews
Home in Kissimmee
Magic-Ready 4BR Pool Home Near Disney
4 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
New place to stay
Guest favourite
Townhouse in Kissimmee
4 BD/ 3 BA/ West Lucaya (8984 SP)
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4 bedrooms, 6 beds, 4.5 bathrooms
16–21 Aug
4.9 out of 5 average rating, 20 reviews
Townhouse in Kissimmee
Disney, Resort Style, 4 BDRM, Sleeps 8, 3 Bath
4 bedrooms, 6 beds, 3 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 bathrooms
26–31 Jul
4.98 out of 5 average rating, 48 reviews
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
1 bed, 1 bathroom
16–21 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Kissimmee
Brand New Designer Townhome | 10 Min to Disney
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds, 3 bathrooms
29 Jul – 3 Aug
4.98 out of 5 average rating, 83 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
31 Jul – 5 Aug
New place to stay
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 80 reviews
Superhost
Home in Kissimmee
Greek Villa w/ Sunny Pool just 20 Min to Disney
4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
New place to stay