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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
Top guest favourite
Flat in Winter Park
The Grove
1 bedroom, 1 queen bed
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
21–26 Aug
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Winter Park
Cute bungalow minutes walk from Park Ave.
2 bedrooms, 2 queen beds
7–13 Nov
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in Winter Park
Luxurious 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds
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
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Guest house in Orlando
College Park Villa Oasis w/ Botanical Courtyard
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.99 out of 5 average rating, 170 reviews
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds
15–20 Aug
Superhost
Flat in Orlando
Spacious2BR PetsFriendly Oasis Sleeps 6, Pool&Gym
2 bedrooms, 3 beds
16–21 Aug
New place to stay
Superhost
Guest house in Orlando
Guest Home| Orlando Airport & Florida Mall 15 min
1 bedroom, 2 beds
21–26 Aug
New place to stay
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds
15–22 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
16–21 Aug
5.0 out of 5 average rating, 78 reviews
Superhost
Guest house in Orlando
Modern Private Studio near Orlando attractions
1 bedroom, 2 beds
16–21 Aug
New place to stay
Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds
17–22 Aug
New place to stay
Top guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom, 1 queen bed
19–24 Aug
4.97 out of 5 average rating, 178 reviews
Home in Orlando
Pool Home + BBQ Grill + Family Friendly
3 bedrooms, 4 beds
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Orlando
~Chic Oasis • 6-Guest Suite • Pool Heat • Near All
2 bedrooms, 3 beds
27 Nov – 2 Dec
4.98 out of 5 average rating, 445 reviews
Guest favourite
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
3 bedrooms, 4 beds
13–18 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Orlando
Sunny Oasis: Downtown Orlando with Suburban feel
2 bedrooms, 2 double beds
14–19 Mar
5.0 out of 5 average rating, 14 reviews