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
,
4.92 out of 5 average rating, 224 reviews
Guest favourite
Home in Clermont
Lakefront 2King 2Twin 1Queen 3BD+Deck Near Events
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Jul
Top guest favourite
Villa in Clermont
Villa for 5 - Visiting family, Golfing, Downtown
4.96 out of 5 average rating, 46 reviews, 2 bedrooms, 4 beds, 2 bathrooms
3–8 Jul
Top guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
4.99 out of 5 average rating, 116 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5.0 out of 5 average rating, 28 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
25–30 Aug
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
6–11 Aug
Villa in Orlando
Charming Orlando Villa with Pool & Family Fun
New place to stay, 4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
Superhost
Apartment in Davenport
2BR Resort Condo Near Disney – Family Ready
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Superhost
Townhouse in Kissimmee
3 BD/ 3 BA/ The Hub At Westside (3349 TT)
New place to stay, 3 bedrooms, 5 beds, 3 bathrooms
28 Jul – 2 Aug
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds, 4 bathrooms
9–14 Sept
Guest favourite
Home in Clermont
Brand 2026 Themed 05 Bedrooms At Windsor Cay
5.0 out of 5 average rating, 5 reviews, 5 bedrooms, 7 beds, 4 bathrooms
16–21 Nov
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
5.0 out of 5 average rating, 23 reviews, 4 bedrooms, 6 beds, 3 bathrooms
8–13 Jul
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 90 reviews, 3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
Townhouse in Clermont
3 BR home with private pool and wifi
3 bedrooms, 3 beds, 3 bathrooms
29 Jul – 3 Aug
Home in Kissimmee
Spacious Condo with Balcony & Golf View at Reunion
New place to stay, 3 bedrooms, 4 beds, 3 bathrooms
18–23 Jul
Superhost
Cottage in Kissimmee
Beauty and the Beast
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
Superhost
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
New place to stay, 4 bedrooms, 6 beds, 2.5 bathrooms
8–13 Aug
Superhost
Townhouse in Kissimmee
5 BD/ 4 BA/ Story Lake (4810 ML)
5 bedrooms, 7 beds, 4 bathrooms
20–25 Jul