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Search results; Over 1,000 homes in Winter Park

Luxe
Home in Winter Park
Rooftop hot tub with mountain views
4 bedrooms, 7 beds, 3.5 private baths
Aug 13 – 18
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4.91 out of 5 average rating, 46 reviews
Top guest favorite
Apartment in Winter Park
Penthouse with hot tub and mountain views
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 3 beds, 3 baths
Aug 13 – 18
Top guest favorite
Apartment in Winter Park
Ski-in/ski-out new build with hot tub
5.0 out of 5 average rating, 43 reviews, 1 bedroom, 4 beds, 1 bath
Aug 23 – 28
Home in Winter Park
Rooftop hot tub with mountain sunset views
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 3 baths
Aug 13 – 18
Top guest favorite
Home in Winter Park
Private hot tub with mountain views
5.0 out of 5 average rating, 24 reviews, 3 bedrooms, 7 beds, 3.5 baths
Aug 28 – Sep 2
Guest favorite
Home in Winter Park
Mountain views with a hot tub downtown
5.0 out of 5 average rating, 29 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 13 – 18
Top guest favorite
Townhouse in Winter Park
New build with a hot tub, near skiing
5.0 out of 5 average rating, 29 reviews, 3 bedrooms, 4 beds, 4 baths
Aug 21 – 26
Top guest favorite
Condo in Winter Park
Newly remodeled with a forest-view deck
5.0 out of 5 average rating, 69 reviews, 2 bedrooms, 6 beds, 2 baths
Aug 25 – 30
Guest favorite
Condo in Winter Park
Walkable to downtown with a fireplace
4.8 out of 5 average rating, 60 reviews, 1 bedroom, 2 beds, 1 bath
Sep 6 – 11
Guest favorite
Apartment in Winter Park
Modern condo with a hot tub and fireplace
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 5 beds, 3 baths
Aug 15 – 20
Guest favorite
Condo in Fraser
Penthouse with hot tub and mountain views
4.93 out of 5 average rating, 27 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 16 – 21
Guest favorite
Condo in Winter Park
Wood-burning fireplace, free ski shuttle
4.94 out of 5 average rating, 161 reviews, 1 bedroom, 3 beds, 1 bath
Aug 13 – 18
Top guest favorite
Condo in Winter Park
Ski-in/ski-out with a hot tub
4.94 out of 5 average rating, 34 reviews, 2 beds, 1 bath
Aug 16 – 21
Condo in Winter Park
Riverfront with pool, 5 min to downtown
New place to stay, 1 bedroom, 2 beds, 1 bath
Aug 25 – 30
Top guest favorite
Condo in Winter Park
Three balconies with mountain views, Winter Park
4.93 out of 5 average rating, 284 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 16 – 21
Superhost
Condo in Winter Park
Remodeled modern rustic with hot tubs
4.87 out of 5 average rating, 119 reviews, 3 bedrooms, 7 beds, 2 baths
Aug 16 – 21
Top guest favorite
Apartment in Fraser
Mountain views from a wrap-around deck
4.96 out of 5 average rating, 102 reviews, 4 bedrooms, 6 beds, 3 baths
Aug 21 – 26
Apartment in Winter Park
Fireplace, fire pit, pool, and jacuzzis
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 2 beds, 1 bath
Aug 18 – 23
Top guest favorite
Condo in Fraser
Valley views, private sauna, and fireplace
4.98 out of 5 average rating, 329 reviews, 2 bedrooms, 5 beds, 2.5 baths
Aug 23 – 28