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Search results; Over 1,000 homes in Windermere

Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
New place to stay
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, 4 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
Superhost
Townhouse in Clermont
5 Bd/ 5.5 Ba/ Windsor Cay (16123 Cl)
5 bedrooms, 7 beds, 5.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
9–14 Nov
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
Disney Area Resort Retreat | Pool, Spa & Mini Golf
3 bedrooms, 7 beds, 2.5 bathrooms
22–27 Aug
New place to stay
Guest favourite
Townhouse in Kissimmee
3 Bd/ 3 Ba/ The Hub At Westside (3349 Tt)
3 bedrooms, 5 beds, 3 bathrooms
13–18 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Four Corners
Luxury 05 Bedroom at Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 29 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
28 Aug – 2 Sept
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 93 reviews
Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds, 5.5 bathrooms
23–28 Aug
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds, 3.5 bathrooms
9–14 Aug
New place to stay
Superhost
Home in Kissimmee
Greek Villa w/ Sunny Pool just 20 Min to Disney
4 bedrooms, 5 beds, 3 bathrooms
2–7 Aug
New place to stay
Superhost
Home in Orlando
Next Epic Universe, OCC, Disney @Vista Cay home
3 bedrooms, 4 beds, 3.5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Orlando
Stunning 4 Bd/ 2 Ba Vista Cay (5048-402 Sl)
4 bedrooms, 6 beds, 2 bathrooms
2–7 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
Home in Kissimmee
Disney World Retreat Oasis & Private Pool
5 bedrooms, 7 beds, 4 bathrooms
2–7 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Orlando
11BR BrandNew | ThemedRooms | Cinema | Game- 11121
11 bedrooms, 15 beds, 11.5 bathrooms
13–18 Aug
5.0 out of 5 average rating, 7 reviews