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Search results; Over 1,000 homes in Winter Park

Guest favourite
Home in Winter Park
Stylish newly updated home in Winter Park
3 bedrooms, 4 beds, 2 private bathrooms
4–9 Sept
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4.98 out of 5 average rating, 204 reviews
Top guest favourite
Apartment in Winter Park
Walk to Park Ave & The WP Village!
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Sept
4.97 out of 5 average rating, 66 reviews
Featured hotel
Hotel in Winter Park
Parlor king
1 bedroom, 1 king bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Winter Park
Luxurious 2BR Near Park Ave & Rollins College
2 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Winter Park
Luxury Designer Home • Downtown,Universal & Disney
4 bedrooms, 4 beds, 3.5 bathrooms
6–11 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, 1 bathroom
18–23 Sept
4.97 out of 5 average rating, 479 reviews
Top guest favourite
Guest house in Orlando
Detached suite in Mills 50 food paradise
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 140 reviews
Top guest favourite
Treehouse in Orlando
Brand New Stylish & Unique Tree House!
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 80 reviews
Top guest favourite
Guest house in Orlando
~Elegant Suite • Luxe Pool • Prime Orlando Stay
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 96 reviews
Top guest favourite
Home in Longwood
The Lakefront Brantley House
3 bedrooms, 3 beds, 2.5 bathrooms
9–16 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Flat in Orlando
Massive Corner 3 Bedroom 2 Bath
3 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 5 reviews
Flat in Orlando
Private Bamboo Oasis Apartment in College Park
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
Top guest favourite
Home in Orlando
Stylish & Cozy King Bed Retreat @ Baldwin Park
2 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Home in Orlando
4BR: Lakefront Retreat with Harry Potter Game Loft
4 bedrooms, 3 bathrooms
22–27 Sept
5.0 out of 5 average rating, 37 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 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, 448 reviews
Top guest favourite
Home in Orlando
M&H Oasis Luxury Heated Pool House
4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 40 reviews
Guest favourite
Townhouse in Oviedo
3BR Villa in Gated Oviedo Near UCF & Orlando
3 bedrooms, 3 beds, 2.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest house in Orlando
College Park Villa Oasis w/ Botanical Courtyard
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 171 reviews