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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
20–25 Aug
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4.95 out of 5 average rating, 466 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Home in Winter Park
Luxurious 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 30 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 Orlando
Spacious 2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 214 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 64 reviews
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
Top guest favourite
Home in Orlando
Walk to Epic Universe | New! 3BR/3.5BA | Vista cay
3 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Kissimmee
Luxe Family Retreat | Pool Villa Near Disney & MCO
5 bedrooms, 8 beds, 2.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest house in Orlando
College Park Villa Oasis w/ Botanical Courtyard
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 171 reviews
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
11–16 Oct
Superhost
Home in Montverde
3BD Montverde Lakeview Escape Near Orlando
3 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
New place to stay
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps 6, Pool&Gym
2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
22–29 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 39 reviews
Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds, 4 bathrooms
20–25 Aug
New place to stay