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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
4–9 Aug
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4.95 out of 5 average rating, 465 reviews
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
4–9 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Winter Park
Stylish 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 7 reviews
Home in Casselberry
Hilltop Haven – Peaceful Casselberry Getaway
3 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
New place to stay
Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 queen beds, 2 bathrooms
7–13 Nov
4.96 out of 5 average rating, 27 reviews
Home in Orlando
Hidden Oasis House - Pool, Gameroom in DT Orlando!
3 bedrooms, 5 beds, 2 bathrooms
5–10 Aug
5.0 out of 5 average rating, 4 reviews
Home in Orlando
Henry Balch Landing
4 bedrooms, 5 beds, 3 bathrooms
5–10 Aug
New place to stay
Top guest favourite
Flat in Orlando
Spacious 2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Orlando
Bright&Airy2BR/2BA Family Oasis Near Airport&Parks
2 bedrooms, 3 beds, 2 bathrooms
4–9 Aug
4.91 out of 5 average rating, 65 reviews
Guest favourite
Home in Orlando
Sleeps 6 | Car Rental | Prime DTO Location
3 bedrooms, 3 beds, 1 bathroom
11–16 Aug
4.95 out of 5 average rating, 83 reviews
Home in Ocoee
Serenity Retreat
2 bedrooms, 2 beds, 2 bathrooms
10–15 Aug
New place to stay
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 104 reviews
Guest favourite
Home in Orlando
Magazine like huge home w/ pool city center/parks
7 bedrooms, 7 beds, 6.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
20–25 Aug
5.0 out of 5 average rating, 39 reviews
Home in Kissimmee
Stylish Disney Retreat | 15 Mins to Disney
3 bedrooms, 4 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Orlando
Sunny Oasis: Downtown Orlando with Suburban feel
2 bedrooms, 2 double beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 63 reviews
Superhost
Townhouse in Kissimmee
SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney
4 bedrooms, 8 beds, 3.5 bathrooms
17–22 Aug
New place to stay