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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
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4.99 out of 5 average rating, 198 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
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed
6–11 Aug
New place to stay
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds
6–11 Aug
4.96 out of 5 average rating, 49 reviews
Home in Kissimmee
Stylish Disney Retreat | 15 Mins to Disney
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 4 reviews
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, 14 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
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
23–28 Aug
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds
6–11 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
9–14 Aug
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Clermont
Game room + pool home near Orlando's top parks
4 bedrooms, 5 beds
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Room in Ocoee
Bedroom and private bathroom
1 queen bed
9–14 Aug
New place to stay
Home in Clermont
New! Windsor Cay Resort | Private Pool | 5BR/5.5BA
5 bedrooms, 6 beds
16–21 Aug
New place to stay
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds
18–23 Oct
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds
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
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
21–26 Aug
New place to stay
Townhouse in Kissimmee
Spacious townhome near Disney w/ patio
4 bedrooms, 6 beds
19–24 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds
1–6 Sept
5.0 out of 5 average rating, 6 reviews