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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
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4.98 out of 5 average rating, 498 reviews
Top guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds, 4 bathrooms
13–18 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Apartment in Winter Park
Luxe 4BR Winter Park Retreat w/ Private Hot Tub
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
4.91 out of 5 average rating, 66 reviews
Guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds, 4 bathrooms
20–25 Sept
4.97 out of 5 average rating, 34 reviews
Superhost
Townhouse in Winter Park
Spacious Mountain Townhome | Private Hot Tub
3 bedrooms, 5 beds, 3 bathrooms
17–22 Sept
4.9 out of 5 average rating, 185 reviews
Superhost
Apartment in Fraser
Meadow Ridge Retreat | Near Winter Park
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
New place to stay
Top guest favourite
Apartment in Winter Park
Beautiful Condo at Winter Park!
1 bedroom, 1 bathroom
8–13 Sept
4.94 out of 5 average rating, 105 reviews
Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds, 3 bathrooms
14–19 Sept
4.92 out of 5 average rating, 78 reviews
Guest favourite
Apartment in Winter Park
Winter Park Ski Resort - Top Floor
1 bedroom, 1 sofa bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 40 reviews
Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds, 2 bathrooms
12–17 Sept
4.87 out of 5 average rating, 122 reviews
Guest favourite
Apartment in Fraser
Alpine Luxe Loft- Hot Tub, Fireplace, Views, Ski
3 bedrooms, 4 beds, 2 bathrooms
30 Oct – 4 Nov
4.91 out of 5 average rating, 32 reviews
Top guest favourite
Apartment in Fraser
Updated Fraser Condo | Trails, Shuttle & W/D
1 bedroom, 2 beds, 1 bathroom
3–8 Oct
4.98 out of 5 average rating, 171 reviews
Top guest favourite
Flat in Winter Park
Modern New build ski in/out. 1br + den.
1 bedroom, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 48 reviews
Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds, 4.5 bathrooms
6–11 Sept
New place to stay
Top guest favourite
Home in Fraser
Mountain Retreat | New Condo | Private Hot Tub
2 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.97 out of 5 average rating, 86 reviews
Superhost
Apartment in Winter Park
Summer Escape • Riverfront Stay in WP
2 bedrooms, 4 beds, 3 bathrooms
7–12 Sept
4.82 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Winter Park
Mountain Town Luxury Penthouse
2 bedrooms, 3 beds, 3 bathrooms
14–19 Oct
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Fraser
Spacious Cabin with Views • Location • Hot Tub
3 bedrooms, 7 beds, 3.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 174 reviews
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds, 4.5 bathrooms
6–11 Sept
4.94 out of 5 average rating, 72 reviews