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Search results; Over 1,000 homes in Windermere

Home in Davenport
Highlands Reserve Retreat | Pool + Spa Near Disney
4 bedrooms, 5 beds, 2 bathrooms
2–7 Oct
New place to stay
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
10–15 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
Superhost
Home in Orlando
Next Epic Universe, OCC, Disney @Vista Cay home
3 bedrooms, 4 beds, 3.5 bathrooms
6–11 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
23–28 Aug
Guest favourite
Home in Kissimmee
Amazing Themed 07 Bedrooms at Solara Resort
7 bedrooms, 10 beds, 5.5 bathrooms
25–30 Oct
4.9 out of 5 average rating, 10 reviews
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds, 4.5 bathrooms
18–23 Oct
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
Top guest favourite
Townhouse in Davenport
4 Bd/3 Bt- Sleeps 8! Close Disney, Self Check-in
4 bedrooms, 5 beds, 3 bathrooms
15–20 Aug
5.0 out of 5 average rating, 24 reviews
Superhost
Home in Kissimmee
Luxury NEW 09 Bedroom/Pool At Solara Resort
9 bedrooms, 13 beds, 6.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Kissimmee
Modern Stay Mins to Disney, Outlets & Walmart
3 bedrooms, 4 beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 6 reviews
Townhouse in Davenport
Beautiful townhouse just 15 minutes from Disney
4 bedrooms, 5 beds, 3 bathrooms
15–20 Aug
New place to stay
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Lucaya Village (8-101)
4 bedrooms, 7 beds, 3 bathrooms
30 Aug – 4 Sept
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
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps6, Pool & Gym
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
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 Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 93 reviews