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Search results; Over 1,000 homes in Winter Park

Guest favourite
Bungalow in Winter Park
Cozy 2/2 Home - Downtown Winterpark/Orlando
2 bedrooms, 2 beds, 2 private bathrooms
17–22 Aug
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4.97 out of 5 average rating, 352 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
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
12–17 Aug
5.0 out of 5 average rating, 5 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, 29 reviews
Top guest favourite
Home in Orlando
The Palm | Stylish Stay Close to Downtown Orlando
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps 6, Pool&Gym
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Guest house in Orlando
College Park Villa Oasis w/ Botanical Courtyard
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 170 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
13–20 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Treehouse in Orlando
Brand New Stylish & Unique Tree House!
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 78 reviews
Top guest favourite
Guest house in Orlando
Guest Home-Orlando Airport and Disney-Free Parking
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
4.96 out of 5 average rating, 53 reviews
Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds, 4 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Home in Orlando
Sunny Oasis: Downtown Orlando with Suburban feel
2 bedrooms, 2 double beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Guest suite in Orlando
~Chic Oasis • 6-Guest Suite • Pool Heat • Near All
2 bedrooms, 3 beds, 1 bathroom
27 Nov – 2 Dec
4.98 out of 5 average rating, 445 reviews
Townhouse in Kissimmee
Magical Family Retreat 4B, 3.5B, Spa, 4M Disney!
4 bedrooms, 8 beds, 3.5 bathrooms
28 Aug – 2 Sept
New place to stay
Room in Orlando
Comfortable room close to everything
1 queen bed, 1 bathroom
11–16 Sept
New place to stay
Home in Orlando
Pool Home + BBQ Grill + Family Friendly
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 4 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