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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
16–21 Jul
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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
4.99 out of 5 average rating, 116 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Jul
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
4.91 out of 5 average rating, 92 reviews, 3 bedrooms, 4 beds, 2 bathrooms
19–24 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
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
Place to stay in Windermere
A room very close to the Disney parks
5.0 out of 5 average rating, 13 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Mar – 2 Apr
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
New place to stay, 7 bedrooms, 6 beds, 4.5 bathrooms
7–12 Dec
Home in Orlando
Hidden Oasis House - Pool, Gameroom in DT Orlando!
3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
Guest favourite
Home in Kissimmee
Orlando Dream Escape | Private Pool | Disney
4.86 out of 5 average rating, 7 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Superhost
Home in Kissimmee
Disney 7 Min • Luxury 4 Suites • Jacuzzi • Arcade
New place to stay, 4 bedrooms, 8 beds, 5 bathrooms
1–6 Aug
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
4.98 out of 5 average rating, 48 reviews, 6 bedrooms, 9 beds, 4 bathrooms
2–7 Aug
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
5.0 out of 5 average rating, 80 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Sept
Guest favourite
Home in Orlando
Tropical Oasis|Lounge|Putting Green|Heated Pool
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Home in Kissimmee
Mayson's Cozy Nest
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Jul
Guest favourite
Home in Orlando
11BR BrandNew | ThemedRooms | Cinema | Game- 11121
5.0 out of 5 average rating, 5 reviews, 11 bedrooms, 15 beds, 11.5 bathrooms
28 Jul – 2 Aug
Superhost
Townhouse in Clermont
5 BD/ 5.5 BA/ Windsor Cay (16123 CL)
5 bedrooms, 7 beds, 5.5 bathrooms
20–25 Sept
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
5.0 out of 5 average rating, 99 reviews, 3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
Top guest favourite
Villa in Orlando
Modern 3BR Family Home Near Shops & Disney
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 4 bathrooms
19–24 Jul
Villa in Clermont
Modern 4BR South Facing Pool Home Near Disney
4 bedrooms, 5 beds, 3 bathrooms
6–11 Sept