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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds, 1 private bathroom
18–23 Aug
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4.9 out of 5 average rating, 106 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds
23–28 Aug
4.91 out of 5 average rating, 94 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed
12–17 Aug
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
Home in Kissimmee
Premium house, 4 bedrooms, sleeps 10, Kissimme
4 bedrooms, 8 beds
24–29 Aug
New place to stay
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
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
4BR Villa | Private Pool • Minutes to Disney
4 bedrooms, 5 beds
12–17 Aug
New place to stay
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds
16–21 Aug
5.0 out of 5 average rating, 28 reviews
Superhost
Home in Kissimmee
7490 Magic Village 8 guests 4,5 baths 8 min Disney
4 bedrooms, 6 beds
12–17 Aug
5.0 out of 5 average rating, 3 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
Room in Gotha
Private Room • Exclusive Bathroom • MCO & Disney
1 queen bed
23–28 Aug
New place to stay
Superhost
Home in Four Corners
2026 BRAND NEW 08BD At Windsor Cay
8 bedrooms, 8 beds
17–22 Aug
New place to stay
Top guest favourite
Flat in Orlando
Luxury 1BR & Resort Amenities - 6min to Epic-Uni
1 bedroom, 2 beds
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds
23–28 Aug
5.0 out of 5 average rating, 104 reviews
Superhost
Home in Gotha
Stylish Home • Sleeps 8 • Near Disney & Universal
3 bedrooms, 6 beds
16–21 Aug
New place to stay
Home in Kissimmee
Kings Castle Retreat
5 bedrooms, 9 beds
16–21 Aug
New place to stay
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds
12–17 Aug
5.0 out of 5 average rating, 12 reviews