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Search results; Over 1,000 homes in Winter Garden

Cottage in Winter Garden
16 Mi to Disney: Cottage w/ Deck in Winter Garden
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
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4.83 out of 5 average rating, 59 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 94 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 58 reviews
Top guest favourite
Flat in Kissimmee
Vacation Condo with pool-20 Min from Disney
2 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Clermont
Modern & Cozy Studio-Apartment
1 bedroom, 2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 11 reviews
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
31 Aug – 5 Sept
New place to stay
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
12–17 Aug
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
23–28 Nov
5.0 out of 5 average rating, 30 reviews
Superhost
Home in Kissimmee
Resort Living | 4BR/3BA | Paradise Palms
4 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
New place to stay
Superhost
Home in Four Corners
2026 BRAND NEW 08BD At Windsor Cay
8 bedrooms, 8 beds, 6 bathrooms
17–22 Aug
New place to stay
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Davenport
The Ultimate Family Getaway Near Disney
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
4.94 out of 5 average rating, 17 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
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, 2.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Townhouse in Clermont
Family Villa w/ Pool + Games • Near Disney (1189)
5 bedrooms, 7 beds, 4.5 bathrooms
19–24 Sept
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Orlando
Walk to Epic Universe | New! 3BR/3.5BA | Vista cay
3 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 reviews
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
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps 6, Pool&Gym
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
New place to stay