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Search results; Over 1,000 homes in Windermere

Guest favourite
Guest house in Windermere
Paradise nook near Orlando's theme parks
1 bedroom, 2 beds, 1 private bathroom
31 Jul – 5 Aug
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4.93 out of 5 average rating, 289 reviews
Top guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
4.99 out of 5 average rating, 116 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
27 Jul – 1 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
22–27 Jul
4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms, 7 beds, 4.5 bathrooms
10–15 Aug
New place to stay
Top guest favourite
Home in Orlando
4BR/2BA Private POOL Home Close to Universal/Parks
4 bedrooms, 5 beds, 2 bathrooms
21–26 Aug
4.94 out of 5 average rating, 117 reviews
Superhost
Home in Clermont
Family pool home w/ game room near Disney
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Kissimmee
5 BD/ 4 BA/ Terra Verde (4669 GB)
5 bedrooms, 7 beds, 4 bathrooms
30 Jul – 4 Aug
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4 bedrooms, 6 beds, 4.5 bathrooms
29 Aug – 3 Sept
4.9 out of 5 average rating, 20 reviews
Guest favourite
Home in Clermont
8 BD/ 6 BA / Windsor Cay (15989 CC)
8 bedrooms, 12 beds, 6 bathrooms
2–7 Nov
5.0 out of 5 average rating, 7 reviews
Home in Kissimmee
Magic-Ready 4BR Pool Home Near Disney
4 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
New place to stay
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
3 bedrooms, 4 beds, 4 bathrooms
26–31 Jul
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Villa in Clermont
Sunset Paradise Villa in Orlando, Disney area.
4 bedrooms, 6 beds, 3 bathrooms
2–7 Aug
5.0 out of 5 average rating, 26 reviews
Home in Kissimmee
Spacious Condo with Balcony & Golf View at Reunion
3 bedrooms, 4 beds, 3 bathrooms
26–31 Jul
New place to stay
Superhost
Flat in Orlando
Stunning 4 BD/ 2 BA Vista Cay (5048-402 SL)
4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
New place to stay
Guest favourite
Villa in Clermont
Villa near Disney with complimentary spa heating!
4 bedrooms, 6 beds, 2 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Orlando
BrandNew 14BR Home | Game and Themed Rooms | 11054
14 bedrooms, 20 beds, 16.5 bathrooms
27 Jul – 1 Aug
New place to stay
Superhost
Townhouse in Clermont
Brand 2026 NEW 05 Bdrms At Windsor Cay
5 bedrooms, 7 beds, 4.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews