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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
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
12–17 Jul
5.0 out of 5 average rating, 24 reviews
Villa in Orlando
Charming Orlando Villa with Pool & Family Fun
4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
New place to stay
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
Superhost
Townhouse in Clermont
Private Pool, BBQ | Steps to Clubhouse
3 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
New place to stay
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
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
4.91 out of 5 average rating, 91 reviews
Top guest favourite
Villa in Clermont
Villa for 5 - Visiting family, Golfing, Downtown
2 bedrooms, 4 beds, 2 bathrooms
7–12 Jul
4.96 out of 5 average rating, 47 reviews
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
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds, 4 bathrooms
9–14 Sept
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
Home in Clermont
Cozy Mod Escape |Sleeps 7| "Oak Tree House"
3 bedrooms, 5 beds, 2 bathrooms
17–22 Jul
5.0 out of 5 average rating, 4 reviews
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
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
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
Superhost
Home in Kissimmee
Beautiful 4 Bedroom Villa – Near Disney Parks
4 bedrooms, 6 beds, 4.5 bathrooms
11–16 Jul
Top guest favourite
Flat in Clermont
Downtown Clermont Scenic Retreat
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 2.5 bathrooms
18–23 Jul
New place to stay