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Search results; Over 1,000 homes in Winter Park

Guest favourite
Home in Winter Park
Spacious & lovely 3 bedroom Winter Park home
3 bedrooms, 4 beds, 2 private bathrooms
9–14 Oct
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4.88 out of 5 average rating, 98 reviews
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Room in Winter Park
Winter Park. room1
1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 5 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
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
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
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
16–23 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, 1 bathroom
14–19 Jan
4.98 out of 5 average rating, 56 reviews
Guest favourite
Home in Orlando
College Park • 2 Kings • WorkSpace • AdventHealth
2 bedrooms, 2 king beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 6 reviews
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
4.97 out of 5 average rating, 451 reviews
Top guest favourite
Guest house in Orlando
Modern 1950s Studio • Near Downtown & Theme Parks
1 bedroom, 1 queen bed, 1 bathroom
17–22 Sept
4.97 out of 5 average rating, 184 reviews
Top guest favourite
Home in Ocoee
Lakefront in West Orlando Florida
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 97 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
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
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
Guest favourite
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
Bungalow in Orlando
Den on Daniels
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
4.98 out of 5 average rating, 146 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
Guest house in Winter Park
Cute & Quaint Private Guesthouse with 1 bed/1 bath
1 bedroom, 1 bed, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 3 reviews