filters

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
,
4.97 out of 5 average rating, 351 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
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, 10 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
9–14 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, 28 reviews
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
12–17 Aug
5.0 out of 5 average rating, 213 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, 9 reviews
Home in Orlando
The Lullaby Retreat | Wekiva & Winter Park
2 bedrooms, 2 beds, 1 bathroom
13–18 Aug
New place to stay
Top guest favourite
Flat in Apopka
The little Manatee Home - Lake & Wildlife Retreat
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 65 reviews
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps 6, Pool&Gym
2 bedrooms, 3 beds, 2 bathrooms
14–19 Aug
New place to stay
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
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
Guest house in Orlando
Guest Home-Orlando Airport and Disney-Free Parking
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 53 reviews
Top guest favourite
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
11–18 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
9–14 Aug
5.0 out of 5 average rating, 77 reviews
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 house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom, 1 queen bed, 1 bathroom
13–18 Aug
4.97 out of 5 average rating, 178 reviews
Top guest favourite
Guest suite in Orlando
~Chic Oasis • 6-Guest Suite • Pool Heat • Near All
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
4.98 out of 5 average rating, 444 reviews