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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Flat in Winter Park
NEW Ski In/Out Condo w/ Hot Tub & Balcony
2 bedrooms, 4 beds, 1 private bathroom
12–17 Sept
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5.0 out of 5 average rating, 52 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
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, 36 reviews
Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 3 bathrooms
10–15 Sept
New place to stay
Guest favourite
Home in Fraser
New Winter Park Townhouse with Great Views!
4 bedrooms, 5 beds, 3.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Apartment in Winter Park
Luxe 4BR Winter Park Retreat w/ Private Hot Tub
4 bedrooms, 5 beds, 3 bathrooms
10–15 Sept
4.91 out of 5 average rating, 67 reviews
Guest favourite
Apartment in Winter Park
Beautiful Condo at Winter Park!
1 bedroom, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 105 reviews
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds, 4.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 72 reviews
Top guest favourite
Guest suite in Fraser
Madge’s Studio Pets welcome!
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 505 reviews
Top guest favourite
Apartment in Winter Park
New Condo Downtown Winter Park-Close to the Slopes
2 bedrooms, 6 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Townhouse in Winter Park
Luxury Ski in/Ski out town home, private hot tub
4 bedrooms, 5 beds, 4.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 63 reviews
Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds, 3.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Winter Park
Duplex In town! Views! PrvtHottub,2Cgarage,Sleeps9
3 bedrooms, 6 beds, 3.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Apartment in Winter Park
Cozy DT condo mins from slopes
2 bedrooms, 3 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 106 reviews
Top guest favourite
Flat in Winter Park
New Hike or Ski in/out Modern Condo-Quiet w/ Views
2 bedrooms, 4 beds, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 42 reviews
Top guest favourite
Apartment in Winter Park
The Rustic Moose
2 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 71 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
Home in Winter Park
Winter Park Pond Chalet 13 - Hot Tub - Views
4 bedrooms, 5 beds, 4 bathrooms
12–17 Sept
4.76 out of 5 average rating, 21 reviews
Top guest favourite
Home in Fraser
Spacious Cabin with Views • Location • Hot Tub
3 bedrooms, 7 beds, 3.5 bathrooms
10–15 Sept
4.95 out of 5 average rating, 174 reviews