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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
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
Superhost
Home in Kissimmee
6 BD/4.5 BA Sleeps 12! Windsor At Westside(8977RS)
6 bedrooms, 8 beds, 4 bathrooms
9–14 Sept
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
Home in Orlando
Hidden Oasis House - Pool, Gameroom in DT Orlando!
3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
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 Clermont
8 BD/ 6 BA / Windsor Cay (15989 CC)
5.0 out of 5 average rating, 7 reviews, 8 bedrooms, 12 beds, 6 bathrooms
6–11 Sept
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
Guest favourite
Townhouse in Kissimmee
4 Beds / 4.5 Baths / Magic Village Views (3085RW)
4.9 out of 5 average rating, 20 reviews, 4 bedrooms, 6 beds, 4.5 bathrooms
16–21 Aug
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
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
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
Guest favourite
Home in Kissimmee
Orlando Dream Escape | Private Pool | Disney
4.88 out of 5 average rating, 8 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
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
Brand NEW 05 Bedrooms At Windsor Cay
4.98 out of 5 average rating, 47 reviews, 5 bedrooms, 7 beds, 4 bathrooms
28 Oct – 2 Nov