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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
16–21 Aug
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4.95 out of 5 average rating, 466 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
21–26 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
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
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, 170 reviews
Room in Orlando
Room with separate entrance and private bathroom
1 bed, 1 bathroom
29 Aug – 3 Sept
New place to stay
Superhost
Home in Orlando
Relax & Recharge • Orlando 4BR with Pool
4 bedrooms, 4 beds, 2.5 bathrooms
15–20 Aug
Home in Orlando
Pool Home + BBQ Grill + Family Friendly
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 4 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
Guest favourite
Home in Orlando
Harmony | Heated Pool | 10 min Universal & Epic.
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 105 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
16–23 Aug
5.0 out of 5 average rating, 24 reviews
Home in Casselberry
Casselberry: Pool, sleep 12, GameRoom, Playground
5 bedrooms, 12 beds, 4 bathrooms
17–22 Aug
New place to stay
Guest favourite
Bungalow in Orlando
Spacious Home in Orlando 1 King 1 Queen
2 bedrooms, 2 beds, 2 bathrooms
30 Sept – 7 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom, 1 queen bed, 1 bathroom
19–24 Aug
4.97 out of 5 average rating, 178 reviews
Superhost
Guest house in Orlando
Guest Home| Orlando Airport & Florida Mall 15 min
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
New place to stay
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
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
Top guest favourite
Guest suite in Altamonte Springs
Guest Suite! Key West in Altamonte Springs!
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
4.96 out of 5 average rating, 446 reviews