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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Home in Winter Garden
Downtown Winter Garden, Florida
2 bedrooms, 2 beds, 1 private bathroom
1–6 Sept
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4.99 out of 5 average rating, 159 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
6–11 Aug
New place to stay
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
6–11 Aug
4.96 out of 5 average rating, 49 reviews
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
Superhost
Home in Clermont
Pool, hot tub & arcade - 19 mins to Disney
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
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, 6 reviews
Room in Ocoee
Bedroom and private bathroom
1 queen bed, 1.5 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
6–11 Aug
5.0 out of 5 average rating, 27 reviews
Townhouse in Davenport
Solterra resort townhouse w/ private pool
4 bedrooms, 5 beds, 3.5 bathrooms
31 Aug – 5 Sept
New place to stay
Top guest favourite
Flat in Orlando
Luxury 1BR & Resort Amenities - 6min to Epic-Uni
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Home in Clermont
New! Windsor Cay Resort | Private Pool | 5BR/5.5BA
5 bedrooms, 6 beds, 5.5 bathrooms
16–21 Aug
New place to stay
Guest favourite
Flat in Kissimmee
8050-112 Luxury 2BR Apt Kissimmee Orlando Disney
2 bedrooms, 3 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 9 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
23–28 Aug
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 Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds, 5.5 bathrooms
3–8 Sept
5.0 out of 5 average rating, 21 reviews
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds, 2 bathrooms
21–26 Aug
New place to stay