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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
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds, 3.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 3 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
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, 5 reviews
Superhost
Home in Orlando
Next Epic Universe, OCC, Disney @Vista Cay home
3 bedrooms, 4 beds, 3.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 4 reviews
Home in Kissimmee
Modern Disney Villa • 7BR • Private Pool
7 bedrooms, 9 beds, 6.5 bathrooms
4–9 Aug
New place to stay
Superhost
Home in Four Corners
7 Bd/ 5.5 Ba/ Windsor Cay (1036 Bp)
7 bedrooms, 10 beds, 5.5 bathrooms
23–28 Aug
Flat in Orlando
Cute, cozy condo - Universal walk
2 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
New place to stay
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
28 Aug – 2 Sept
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
Home in Orlando
Henry Balch Landing
4 bedrooms, 5 beds, 3 bathrooms
5–10 Aug
New place to stay
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds, 4 bathrooms
10–15 Aug
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
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
4–9 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Clermont
Pool, hot tub & arcade - 19 mins to Disney
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 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
Spacious Condo with Balcony & Golf View at Reunion
3 bedrooms, 4 beds, 3 bathrooms
6–11 Aug
New place to stay
Guest favourite
Home in Kissimmee
NEW 07 Bedroom Themed Luxury in Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
23–28 Aug
4.94 out of 5 average rating, 18 reviews