filters

Search results; Over 1,000 homes in Winter Garden

Cottage in Winter Garden
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
2 bedrooms, 3 beds, 1 private bathroom
1–6 Aug
,
4.89 out of 5 average rating, 122 reviews
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
31 Aug – 5 Sept
New place to stay
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 11 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
28 Aug – 2 Sept
Home in Kissimmee
Sleeps 13-Park Shuttle-Themed Rooms-Solara Resort
5 bedrooms, 8 beds, 5.5 bathrooms
1–6 Aug
New place to stay
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
4.91 out of 5 average rating, 93 reviews
Home in Four Corners
The Epic Escape Mansion 9Br near Disney/Universal
9 bedrooms, 20 beds, 5 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
8–13 Aug
5.0 out of 5 average rating, 13 reviews
Superhost
Townhouse in Four Corners
Gorgeous Villa w/ Mickey Room, Private Pool & More
4 bedrooms, 8 beds, 3 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
9–14 Nov
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
1–6 Aug
4.97 out of 5 average rating, 38 reviews
Home in Kissimmee
5BR Villa near Disney | Game Room, Pool & Hot Tub
5 bedrooms, 8 beds, 3.5 bathrooms
3–8 Sept
New place to stay
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
31 Dec – 5 Jan
5.0 out of 5 average rating, 9 reviews
Flat in Winter Garden
Chic Studio Apt by Bike Trail & Downtown, Apt #4
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
New place to stay
Superhost
Townhouse in Davenport
Luxury Stay 5BR at Windsor Island - Near Disney
5 bedrooms, 7 beds, 5.5 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Davenport
Home Away from Home + 2 suites
5 bedrooms, 6 beds, 3 bathrooms
21–26 Oct
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Clermont
Hidden Springs retreat w/ pool, spa & game room
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 reviews
Home in Clermont
Lakeview Pool & Spa Retreat w/ Private Theater
4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
New place to stay
Guest favourite
Home in Kissimmee
Magic Palms Villa
6 bedrooms, 9 beds, 3 bathrooms
14–19 Aug
5.0 out of 5 average rating, 6 reviews