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Search results; Over 1,000 homes in Winter Park

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Guest favourite
Apartment in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds, 1 private bathroom
20–25 Sept
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4.94 out of 5 average rating, 165 reviews
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Top guest favourite
Home in Fraser
Mountain Retreat | New Condo | Private Hot Tub
2 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
4.97 out of 5 average rating, 87 reviews
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Guest favourite
Home in Fraser
New Winter Park Townhouse with Great Views!
4 bedrooms, 5 beds, 3.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds, 4 bathrooms
11–16 Oct
4.97 out of 5 average rating, 36 reviews
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Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Apartment in Fraser
Bright Modern Mountain Getaway | Views + Garage
2 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 50 reviews
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Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
New place to stay
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Top guest favourite
Apartment in Winter Park
Downtown Mtn Oasis + Hot Tubs | Steps to Events
2 bedrooms, 5 beds, 3 bathrooms
18–23 Sept
4.96 out of 5 average rating, 114 reviews
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Guest favourite
Home in Winter Park
Winter Park Pond Chalet 13 - Hot Tub - Views
4 bedrooms, 5 beds, 4 bathrooms
11–16 Oct
4.77 out of 5 average rating, 22 reviews
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Guest favourite
Flat in Winter Park
The Little Palace-Full Amenities
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 54 reviews
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Guest favourite
Townhouse in Winter Park
Luxury Ski in/Ski out town home, private hot tub
4 bedrooms, 5 beds, 4.5 bathrooms
18–23 Sept
4.92 out of 5 average rating, 64 reviews
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Top guest favourite
Flat in Winter Park
Luxury Winter Park Studio*PrivHotTub*Majestic View
1 bedroom, 1 king bed, 1 bathroom
15–20 Nov
4.97 out of 5 average rating, 135 reviews
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Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds, 4.5 bathrooms
18–23 Sept
4.94 out of 5 average rating, 72 reviews
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Top guest favourite
Flat in Winter Park
New Hike or Ski in/out Modern Condo-Quiet w/ Views
2 bedrooms, 4 beds, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 42 reviews
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Guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds, 4 bathrooms
10–15 Oct
4.97 out of 5 average rating, 36 reviews
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Guest favourite
Apartment in Fraser
Alpine Luxe Loft- Hot Tub, Fireplace, Views, Ski
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.91 out of 5 average rating, 33 reviews
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Top guest favourite
Home in Winter Park
Winter Park Home | Hot Tub Sauna Walk to Downtown
4 bedrooms, 5 beds, 3.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Apartment in Winter Park
Winter Park Ski Resort - Top Floor
1 bedroom, 1 sofa bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 41 reviews
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Top guest favourite
Apartment in Fraser
Walk to Restaurants! Enjoy Cool Fall Days!
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 148 reviews