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Search results; Over 1,000 homes in Winter Park

Superhost
Guest house in Winter Park
Cozy guest house close to Downtown Orlando
1 bedroom, 2 beds, 1 private bathroom
14–19 Sept
,
4.86 out of 5 average rating, 195 reviews
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Winter Park
Apt D -Modern Elegance in the Heart of Winter Park
2 bedrooms, 2 queen beds
17–22 Sept
4.96 out of 5 average rating, 235 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
Room in Winter Park
LBeTwo Queen desk closet
1 bed
19–24 Sept
New place to stay
Top guest favourite
Home in Orlando
Not just 2 private bedrooms; the entire upstairs!
2 bedrooms, 2 beds
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
12–17 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Orlando
Spacious2BR PetFriendly Oasis Sleeps 6, Pool &Gym
2 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed
7–12 Sept
5.0 out of 5 average rating, 142 reviews
Top guest favourite
Home in Orlando
4BR: Lakefront Retreat with Harry Potter Game Loft
4 bedrooms
12–17 Oct
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Flat in Orlando
Luxury 1BR & Resort Amenities - 6min to Epic-Uni
1 bedroom, 2 beds
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds
9–16 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Guest house in Orlando
~ Luxe Modern Suite • Heated Pool • 2BR Gem
2 bedrooms, 2 beds
14–19 Jan
4.98 out of 5 average rating, 54 reviews
Room in Oviedo
Modern Oviedo Stay | Cozy & Peaceful Nature Suite
1 queen bed
11–16 Sept
New place to stay
Guest favourite
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 bedroom, 1 queen bed
19–24 Oct
4.98 out of 5 average rating, 481 reviews
Flat in Orlando
Private Bamboo Oasis Apartment in College Park
1 bedroom, 1 bed
7–12 Sept
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds
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
7–12 Sept