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Search results; Over 1,000 homes in Windermere

Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
New place to stay
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
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
Home in Clermont
New! Windsor Cay Resort | Private Pool | 5BR/5.5BA
5 bedrooms, 6 beds, 5.5 bathrooms
16–21 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
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
Superhost
Townhouse in Clermont
5 BD/ 4.5 BA/ Windsor Cay (16218 CC)
5 bedrooms, 7 beds, 4.5 bathrooms
18–23 Oct
Superhost
Home in Kissimmee
7490 Magic Village 8 guests 4,5 baths 8 min Disney
4 bedrooms, 6 beds, 4.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Home in Kissimmee
Simply Magical | 13 PPL | Pool | Mini Golf | Games
4 bedrooms, 6 beds, 3 bathrooms
10–15 Aug
New place to stay
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
Superhost
Home in Clermont
10 Bd/ 8 Ba/ Windsor Cay (1031 Cr)
10 bedrooms, 15 beds, 8 bathrooms
16–21 Aug
Home in Kissimmee
Modern Disney Villa • 7BR • Private Pool
7 bedrooms, 9 beds, 6.5 bathrooms
10–15 Aug
Superhost
Flat in Orlando
Stunning 4 Bd/ 2 Ba Vista Cay (5048-402 Sl)
4 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 3 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
Superhost
Home in Four Corners
2026 Themed 07 Bedrooms At Windsor Cay
7 bedrooms, 8 single beds, 5 bathrooms
28 Nov – 3 Dec
Superhost
Home in Kissimmee
2026 Luxry Themed 06 Bedrooms At Solara Resort
6 bedrooms, 8 beds, 4.5 bathrooms
14–19 Sept
Guest favourite
Home in Kissimmee
NEW! Disney-Themed Escape | Private Pool | Villans
8 bedrooms, 13 beds, 6 bathrooms
18–23 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
14–19 Aug
5.0 out of 5 average rating, 104 reviews