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Search results; Over 1,000 homes in Windermere

Descriptions are based on details hosts provide
Guest favourite
Guest house in Windermere
Paradise nook near Orlando's theme parks
1 bedroom, 2 beds, 1 private bathroom
17–22 Jul
,
4.93 out of 5 average rating, 289 reviews
Top guest favourite
Flat in Windermere
Relaxing 2BR Lakeview Retreat Close to Attractions
4.99 out of 5 average rating, 116 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Jul
Top guest favourite
Home in Ocoee
Lakefront with a beach and fire pit
4.91 out of 5 average rating, 92 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Orlando
Remodeled pool home in Doctor Phillips
4.94 out of 5 average rating, 117 reviews, 4 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
Home in Kissimmee
Spacious Condo with Balcony & Golf View at Reunion
New place to stay, 3 bedrooms, 4 beds, 3 bathrooms
18–23 Jul
Top guest favourite
Flat in Orlando
New 1 Bedroom Suite with full kitchen, Bathroom #1
4.96 out of 5 average rating, 23 reviews, 1 bedroom, 2 beds, 1 bathroom
20–25 Jul
Top guest favourite
Place to stay in Windermere
Pool and free parking near Disney
5.0 out of 5 average rating, 13 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Mar – 2 Apr
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
4.99 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Superhost
Home in Clermont
2026 NEW! Stunning 09 Bedroom at Windsor Cay
New place to stay, 9 bedrooms, 12 beds, 6 bathrooms
1–6 Aug
Home in Orlando
Pool and game room in central Orlando
3 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Top guest favourite
Home in Clermont
Private pool, spa, and game room
4.98 out of 5 average rating, 48 reviews, 6 bedrooms, 9 beds, 4 bathrooms
26–31 Jul
Superhost
Flat in Orlando
Stunning 4 BD/ 2 BA Vista Cay (5048-402 SL)
New place to stay, 4 bedrooms, 6 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Minneola
Pool with LED lights and a fire pit
5.0 out of 5 average rating, 80 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Sept
Superhost
Home in Kissimmee
Pool home with game room near Disney
New place to stay, 7 bedrooms, 6 beds, 4.5 bathrooms
31 Jul – 5 Aug
Guest favourite
Home in Clermont
Private screened-in pool near Disney
5.0 out of 5 average rating, 7 reviews, 8 bedrooms, 12 beds, 6 bathrooms
6–11 Sept
Home in Kissimmee
Mayson's Cozy Nest
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 Jul
Superhost
Room in Winter Garden
Haven 15 minutes from Disney
5.0 out of 5 average rating, 4 reviews, 1 bed, 1 bathroom
16–21 Jul
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept