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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
17–22 Aug
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4.91 out of 5 average rating, 290 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.91 out of 5 average rating, 94 reviews
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds, 4.5 bathrooms
18–23 Oct
Guest favourite
Townhouse in Kissimmee
3 Bd/ 3 Ba/ The Hub At Westside (3349 Tt)
3 bedrooms, 5 beds, 3 bathrooms
22–27 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Davenport
Pool Spa + Outdoor Entertainment | Golf Retreat
4 bedrooms, 6 beds, 5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Townhouse in Kissimmee
3 Bd/ 2.5 Ba/ Encantada Resort (3113 Yl)
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Flat in Orlando
Luxe King En-Suite• Universal/Epic 6 mins• Getaway
2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
5.0 out of 5 average rating, 4 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
New place to stay
Top guest favourite
Home in Orlando
Next Epic Universe, OCC, Disney @Vista Cay home
3 bedrooms, 4 beds, 3.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Kissimmee
Montego Bay Retreat | 15 Min to Disney
3 bedrooms, 5 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 12 reviews
Superhost
Townhouse in Clermont
5BR Private Pool Home at Windsor Cay Near Disney
5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Aug
New place to stay
Superhost
Flat in Orlando
Stunning 4 Bd/ 2 Ba Vista Cay (5048-402 Sl)
4 bedrooms, 6 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Orlando
New 1 Bedroom Suite with full kitchen, Bathroom #1
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 25 reviews
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds, 4.5 bathrooms
14–19 Sept
Superhost
Home in Clermont
10 Bd/ 8 Ba/ Windsor Cay (1031 Cr)
10 bedrooms, 15 beds, 8 bathrooms
16–21 Aug
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, 84 reviews
Top guest favourite
Home in Clermont
Cozy Clermont Retreat
6 bedrooms, 9 beds, 4 bathrooms
21–26 Aug
4.98 out of 5 average rating, 51 reviews
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
28 Nov – 3 Dec
Home in Kissimmee
4BR Kissimmee home with private pool
4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
New place to stay