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Search results; Over 1,000 homes in Winter Garden

Guest favourite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
1 bedroom, 1 bed, 1 private bathroom
2–7 Aug
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4.92 out of 5 average rating, 224 reviews
Villa in Orlando
Charming Orlando Villa with Pool & Family Fun
4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
New place to stay
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
8–13 Jul
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
6–11 Mar
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
6–11 Sept
Superhost
Home in Clermont
2026 Brand NEW 10 Bedrooms At Windsor Cay
10 bedrooms, 16 beds, 8 bathrooms
15–20 Aug
New place to stay
Top guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
4.99 out of 5 average rating, 116 reviews
Top guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
3 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
30 Jul – 4 Aug
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Villa in Clermont
Villa for 5 - Visiting family, Golfing, Downtown
2 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
4.96 out of 5 average rating, 47 reviews
Superhost
Townhouse in Clermont
Private Pool, BBQ | Steps to Clubhouse
3 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
New place to stay
Superhost
Cottage in Kissimmee
Beauty and the Beast
2 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
New place to stay
Guest favourite
Townhouse in Kissimmee
NEW 05 Bedrooms at Windsor Westside
5 bedrooms, 9 beds, 4.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest suite in Clermont
Modern Guesthouse Suite
1 bedroom, 1 king bed, 1 bathroom
21–26 Jul
4.97 out of 5 average rating, 31 reviews
Superhost
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
3 bedrooms, 5 beds, 3 bathrooms
28 Jul – 2 Aug
Superhost
Townhouse in Four Corners
Gorgeous Villa w/ Mickey Room, Private Pool & More
4 bedrooms, 8 beds, 3 bathrooms
18–23 Jul
New place to stay
Superhost
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
12–17 Jul
New place to stay
Top guest favourite
Guest house in Winter Garden
A place with a view
2 bedrooms, 3 beds, 1 bathroom
3–8 Aug
4.9 out of 5 average rating, 104 reviews