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Search results; Over 1,000 homes in Winter Garden

Top guest favourite
Home in Winter Garden
Downtown Bungalow with fire pit and putting green
2 bedrooms, 2 beds, 1 private bathroom
1–6 Sept
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4.97 out of 5 average rating, 132 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 95 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
18–23 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
27 Aug – 1 Sept
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds, 6 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Clermont
Modern & Cozy Studio-Apartment
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 12 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
17–22 Aug
Rooms in Apopka
Spacious close to everything Orlando has to offer
4 bedrooms, 4 beds, 2 bathrooms
18–23 Aug
New place to stay
Top guest favourite
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 5 reviews
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, 7 reviews
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
New place to stay
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
1 bed, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Guest house in Orlando
Modern Private Studio near Orlando attractions
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
New place to stay
Room in Ocoee
Bedroom and private bathroom
1 queen bed, 1.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Rooms in Oakland
Oakland Trails
2 bedrooms, 2 queen beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 45 reviews