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Search results; Over 1,000 homes in Winter Garden

Superhost
Apartment in Winter Garden
Pet-friendly Resort Getaway with Patio and Pool
2 bedrooms, 3 beds, 2 private bathrooms
2–7 Sept
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4.69 out of 5 average rating, 70 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
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
Flat in Kissimmee
Vacation Condo with pool-20 Min from Disney
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Townhouse in Clermont
The gold cottage
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.89 out of 5 average rating, 56 reviews
Top guest favourite
Villa in Clermont
Visiting Family, Lakes, Golf, Olympus, the Mouse?
2 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
4.96 out of 5 average rating, 49 reviews
Guest favourite
Home in Clermont
Stunning 5B/4.5B, Heated Pool & BBQ
5 bedrooms, 7 beds, 4.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 18 reviews
Superhost
Townhouse in Four Corners
Gorgeous Villa w/ Mickey Room, Private Pool & More
4 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
New place to stay
Home in Kissimmee
Stylish Disney Retreat | 15 Mins to Disney
3 bedrooms, 4 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
3–8 Aug
5.0 out of 5 average rating, 27 reviews
Townhouse in Davenport
Mirage Family Haven @ Regal Palms | Sage Vacations
3 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 81 reviews
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
Townhouse in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (16123 Cl)
5 bedrooms, 7 beds, 5.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Clermont
2026 Cozy Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 7 beds, 4 bathrooms
22–27 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Clermont
2026 NEW Themed 05 Bedrooms At Windsor Cay
5 bedrooms, 8 beds, 4 bathrooms
7–12 Feb
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Clermont
Pool, hot tub & arcade - 19 mins to Disney
4 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 reviews