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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Cottage in Winter Park
Winter Park Pearl 6 min drive to historic Park Ave
3 bedrooms, 3 beds, 1.5 private bathrooms
1–6 Aug
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4.95 out of 5 average rating, 463 reviews
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
2–7 Aug
Top guest favourite
Home in Winter Park
Modern 2BR Near Park Ave Perfect for Groups
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Guest favourite
Flat in Winter Park
The Grove
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Top guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
4.99 out of 5 average rating, 79 reviews, 3 bedrooms, 3 beds, 1 bathroom
12–17 Aug
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
Home in Orlando
Hidden Oasis House - Pool, Gameroom in DT Orlando!
3 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Home in Longwood
Central Florida Pool Home
4.96 out of 5 average rating, 54 reviews, 3 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Home in Ocoee
Serenity Retreat
New place to stay, 2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
5.0 out of 5 average rating, 38 reviews, 4 bedrooms, 5 beds, 2 bathrooms
2–7 Aug
Superhost
Home in Kissimmee
Jungle pool home w/ hot tub - close to Disney
New place to stay, 4 bedrooms, 7 beds, 3 bathrooms
17–22 Aug
Top guest favourite
Townhouse in Orlando
Fun Family Townhome with Pool and Game Room!
5.0 out of 5 average rating, 8 reviews, 5 bedrooms, 9 beds, 5 bathrooms
23–28 Aug
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
5.0 out of 5 average rating, 63 reviews, 2 bedrooms, 2 beds, 2 bathrooms
22–27 Aug
Guest favourite
Home in Orlando
Magazine like huge home w/ pool city center/parks
5.0 out of 5 average rating, 6 reviews, 7 bedrooms, 7 beds, 6.5 bathrooms
31 Aug – 5 Sept
Superhost
Townhouse in Orlando
New Vista Cay Home | Universal & Convention
New place to stay, 3 bedrooms, 4 beds, 3.5 bathrooms
2–7 Aug
Top guest favourite
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 2 bathrooms
8–13 Aug
Top guest favourite
Cottage in Kissimmee
Beauty and the Beast
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
Guest favourite
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug