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Search results; Over 1,000 homes in Winter Park

Home in Winter Park
Gem. Downtown Winter park, walk to Park av/Rollins
3 bedrooms, 6 beds, 2 private bathrooms
2–7 Oct
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4.9 out of 5 average rating, 143 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds
3–8 Oct
5.0 out of 5 average rating, 7 reviews
Room in Winter Park
Winter Park. room1
1 queen bed
20–25 Sept
5.0 out of 5 average rating, 4 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
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds
14–21 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Guest suite in Orlando
~Chic Oasis • 6-Guest Suite • Pool Heat • Near All
2 bedrooms, 3 beds
27 Nov – 2 Dec
4.97 out of 5 average rating, 451 reviews
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed
13–18 Sept
5.0 out of 5 average rating, 3 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
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
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed
19–24 Sept
5.0 out of 5 average rating, 142 reviews
Top guest favourite
Flat in Orlando
Villa Magical by Boho Luxe •Top1% |FreeParkShuttle
1 bedroom, 5 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Bungalow in Orlando
Den on Daniels
1 bedroom, 1 bed
13–18 Sept
4.98 out of 5 average rating, 145 reviews
Top guest favourite
Guest house in Orlando
College Park Villa Oasis w/ Botanical Courtyard
1 bedroom, 1 queen bed
21–26 Sept
4.99 out of 5 average rating, 171 reviews
Top guest favourite
Guest suite in Orlando
A SUITE RETREAT with a Garden View in the City
1 bedroom, 1 queen bed
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
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Apartment in Orlando
4114-306 Spacious 3bd condo at Vista Cay Resort
3 bedrooms, 7 beds
6–11 Oct
New place to stay
Room in Orlando
Orlando Comfort
2 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest house in Orlando
1924 Spanish Carriage House Lower
1 bedroom, 2 beds
12–17 Sept
4.98 out of 5 average rating, 154 reviews
Guest favourite
Apartment in Orlando
Vista Cay Lakeview Chic, Next To Epic And Occc
2 bedrooms, 3 beds
25–30 Sept
5.0 out of 5 average rating, 71 reviews