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Search results; Over 1,000 homes in Winter Garden

Top 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
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
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
6–11 Aug
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Clermont
Brand New 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 2.5 bathrooms
8–13 Aug
New place to stay
Superhost
Townhouse in Clermont
Private Pool, BBQ | Steps to Clubhouse
3 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
New place to stay
Home in Kissimmee
Santosh Cove Retreat
4 bedrooms, 5 beds, 3.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 3 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
New place to stay
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
Flat in Clermont
Downtown Clermont Scenic Retreat
2 bedrooms, 2 beds, 1.5 bathrooms
4–9 Jul
5.0 out of 5 average rating, 13 reviews
Superhost
Apartment in Davenport
2BR Resort Condo Near Disney – Family Ready
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Villa in Clermont
Villa for 5 - Visiting family, Golfing, Downtown
2 bedrooms, 4 beds, 2 bathrooms
4–9 Jul
4.96 out of 5 average rating, 47 reviews
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, 23 reviews
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
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
Townhouse in Kissimmee
5 BD/ 4 BA/ Story Lake (4810 ML)
5 bedrooms, 7 beds, 4 bathrooms
20–25 Jul
Top guest favourite
Home in Kissimmee
Luxury Home Orlando – approx. 10 min to Disney
3 bedrooms, 4 beds, 3 bathrooms
13–18 Aug
4.98 out of 5 average rating, 80 reviews
Home in Kissimmee
NEW! Disney-Themed Escape | Private Pool | Villans
8 bedrooms, 13 beds, 6 bathrooms
6–11 Jul
New place to stay