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Search results; Over 1,000 homes in Winter Park

Guest favourite
Apartment in Winter Park
Charming 2/1 Condo on a Lake in Winter Park
2 bedrooms, 2 beds, 1 private bathroom
29 Oct – 3 Nov
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4.95 out of 5 average rating, 39 reviews
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 3 reviews
Flat in Orlando
Carriage House w/ Office - Thornton Park/Lake Eola
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
New place to stay
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 214 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 142 reviews
Room in Winter Park
LBeTwo Queen desk closet
1 bed, 1 bathroom
19–24 Sept
New place to stay
Guest favourite
Flat in Altamonte Springs
Lake Marion Apt w/ Canoe in Altamonte Springs!
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.89 out of 5 average rating, 93 reviews
Guest favourite
Room in Orlando
Stylish Private bd/bth. 5% wkly/10% mthly discount
1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 bedroom, 1 queen bed, 1 bathroom
18–23 Nov
4.98 out of 5 average rating, 482 reviews
Top guest favourite
Home in Orlando
4BR: Lakefront Retreat with Harry Potter Game Loft
4 bedrooms, 3 bathrooms
12–17 Oct
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Flat in Orlando
Luxury King, Close to Parks, PetFriendly,Pool, Gym
1 bedroom, 2 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
15–22 Sept
5.0 out of 5 average rating, 24 reviews
Room in Orlando
Orlando Comfort
2 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds, 1 bathroom
14–19 Jan
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 65 reviews
Room in Winter Park
Quiet, comfortable room in Orlando (Winter Park)
1 bed, 1 bathroom
14–19 Sept
Room in Oviedo
Modern Oviedo Stay | Cozy & Peaceful Nature Suite
1 queen bed, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Bungalow in Orlando
Den on Daniels
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 146 reviews