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Search results; Over 1,000 homes in Windermere

Home in Clermont
New! Windsor Cay Resort | Private Pool | 5BR/5.5BA
5 bedrooms, 6 beds, 5.5 bathrooms
16–21 Aug
New place to stay
Superhost
Home in Kissimmee
Resort Living | 4BR/3BA | Paradise Palms
4 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
New place to stay
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
Top guest favourite
Flat in Orlando
New 1 Bedroom Suite with full kitchen, Bathroom #1
1 bedroom, 2 beds, 1 bathroom
8–13 Aug
4.96 out of 5 average rating, 25 reviews
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds, 4.5 bathrooms
18–23 Oct
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 104 reviews
Superhost
Home in Clermont
Game room + pool home near Orlando's top parks
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Superhost
Flat in Orlando
Spacious 2BR Oasis, Sleeps 8 Near Orlando Parks
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Orlando
Next Epic Universe, OCC, Disney @Vista Cay home
3 bedrooms, 4 beds, 3.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 6 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
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Kissimmee
Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
3 bedrooms, 5 beds, 2 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 40 reviews
Home in Kissimmee
Disney Area Resort Retreat | Pool, Spa & Mini Golf
3 bedrooms, 7 beds, 2.5 bathrooms
5–10 Oct
New place to stay
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
Townhouse in Kissimmee
Spacious townhome near Disney w/ patio
4 bedrooms, 6 beds, 4.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 8 reviews
Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
2–7 Oct
New place to stay