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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
19–24 Aug
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4.93 out of 5 average rating, 291 reviews
Top guest favourite
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Kissimmee
Vacation Condo with pool-20 Min from Disney
2 bedrooms, 5 beds, 2 bathrooms
30 Aug – 4 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Apartment in Orlando
Super Mario's Sky Suite - Epic Universe 3 BD SUITE
3 bedrooms, 4 beds, 2 bathrooms
27 Aug – 1 Sept
4.95 out of 5 average rating, 189 reviews
Townhouse in Kissimmee
Magical Family Retreat 4B, 3.5B, Spa, 4M Disney!
4 bedrooms, 8 beds, 3.5 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.92 out of 5 average rating, 95 reviews
Superhost
Home in Clermont
2026 Brand NEW 08 Bedrooms At Windsor Cay
8 bedrooms, 9 single beds, 6 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Home in Davenport
Magical Florida Stay | Pool & Harry Potter
3 bedrooms, 6 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Orlando
New 1 Bedroom Suite with full kitchen, Bathroom #1
1 bedroom, 2 beds, 1 bathroom
19–24 Aug
4.96 out of 5 average rating, 25 reviews
Home in Kissimmee
Premium house, 4 bedrooms, sleeps 10, Kissimme
4 bedrooms, 8 beds, 3 bathrooms
24–29 Aug
New place to stay
Superhost
Flat in Orlando
Spacious 2BR Oasis, Sleeps 8 Near Orlando Parks
2 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Orlando
New luxury 3BD in Vista Cay · 5 min Epic Universe
3 bedrooms, 6 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Davenport
Remodeled 5BR | Pool, Theater & Themed Rooms
5 bedrooms, 7 beds, 5.5 bathrooms
26–31 Aug
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, 85 reviews
Superhost
Home in Kissimmee
7 Bd/ 6 Ba/ Storey Lake (4585 Tb)
7 bedrooms, 10 beds, 6 bathrooms
27 Aug – 1 Sept
New place to stay
Guest favourite
Apartment in Kissimmee
406 - Toy Story & Safari Dream Condo
3 bedrooms, 4 beds, 2 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Guest house in Orlando
Guest Home| Orlando Airport & Florida Mall 15 min
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
New place to stay
Superhost
Townhouse in Kissimmee
4 Bd/ 3 Ba/ Lucaya Village (8-101)
4 bedrooms, 7 beds, 3 bathrooms
6–11 Sept
Guest favourite
Home in Kissimmee
Amazing Home Near Parks w/ Pool & Spa
4 bedrooms, 5 beds, 4 bathrooms
24–29 Oct
5.0 out of 5 average rating, 7 reviews