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Search results; Over 1,000 homes in Winter Garden

Superhost
Home in Winter Garden
Downtown Winter Garden Luxury Retreat (NO Parties)
3 bedrooms, 3 beds, 1 private bathroom
7–12 Sept
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4.9 out of 5 average rating, 29 reviews
Top guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 28 reviews
Home in Clermont
25 miles to Disney Contry side house
4 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
New place to stay
Superhost
Home in Four Corners
8 BD/ 5.5 BA/ Windsor Cay (1016 BW)
8 bedrooms, 13 beds, 5.5 bathrooms
15–20 Sept
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 bathrooms
1–6 Sept
4.98 out of 5 average rating, 51 reviews
Superhost
Rooms in Oakland
Oakland Trails
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)
5 bedrooms, 7 beds, 5.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 21 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
Home in Kissimmee
Premium house, 4 bedrooms, sleeps 10, Kissimme
4 bedrooms, 8 beds, 3 bathrooms
1–6 Sept
New place to stay
Superhost
Home in Kissimmee
6 Bd/ 5 Ba/ Solara Resort (9038 Sr)
6 bedrooms, 11 beds, 5 bathrooms
6–11 Sept
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 85 reviews
Superhost
Home in Clermont
Experience Our New 2026 10BR Home at Windsor Cay
10 bedrooms, 12 beds, 8 bathrooms
13–18 Sept
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Lucaya Village (8-101)
4 bedrooms, 7 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 4 reviews
Townhouse in Kissimmee
Magical Family Retreat 4B, 3.5B, Spa, 4M Disney!
4 bedrooms, 8 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Townhouse in Kissimmee
Disney Retreat w/ Private Pool & Resort Access
5 bedrooms, 7 beds, 4.5 bathrooms
1–6 Sept
New place to stay