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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
2 bedrooms, 3 beds, 1 bathroom
17–22 Jul
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
19–24 Jul
4.91 out of 5 average rating, 92 reviews
Top guest favourite
Flat in Orlando
New 1 Bedroom Suite with full kitchen, Bathroom #1
1 bedroom, 2 beds, 1 bathroom
20–25 Jul
4.96 out of 5 average rating, 23 reviews
Home in Kissimmee
Spacious Condo with Balcony & Golf View at Reunion
3 bedrooms, 4 beds, 3 bathrooms
18–23 Jul
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
Top guest favourite
Place to stay in Windermere
A room very close to the Disney parks
1 bedroom, 1 bed, 1 bathroom
28 Mar – 2 Apr
5.0 out of 5 average rating, 13 reviews
Home in Kissimmee
Magic-Ready 4BR Pool Home Near Disney
4 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
New place to stay
Superhost
Home in Kissimmee
Greek Villa w/ Sunny Pool just 20 Min to Disney
4 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
New place to stay
Home in Orlando
Hidden Oasis House - Pool, Gameroom in DT Orlando!
3 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
Superhost
Home in Kissimmee
2026 NEW 7BR Pool Home Near Disney | Solara Resort
7 bedrooms, 6 single beds, 4.5 bathrooms
7–12 Dec
New place to stay
Top guest favourite
Home in Minneola
New! Resort Style Oasis ~ Heated Pool & Game Room
3 bedrooms, 3 queen beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 80 reviews
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
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.99 out of 5 average rating, 78 reviews
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
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 bathrooms
26–31 Jul
4.98 out of 5 average rating, 48 reviews
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4 bedrooms, 6 beds, 4.5 bathrooms
16–21 Aug
4.9 out of 5 average rating, 20 reviews
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds, 4 bathrooms
9–14 Sept
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 100 reviews