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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Flat in Winter Park
Tipsy Fox @ Downtown Winter Park Near the Slopes!
1 bedroom, 2 beds, 1 private bathroom
4–9 Oct
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4.95 out of 5 average rating, 163 reviews
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Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
4.87 out of 5 average rating, 123 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
Apartment in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 165 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
27 Sept – 2 Oct
4.92 out of 5 average rating, 64 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
18–23 Oct
4.97 out of 5 average rating, 36 reviews
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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
20–25 Sept
4.96 out of 5 average rating, 114 reviews
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Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds, 3 bathrooms
5–10 Oct
4.92 out of 5 average rating, 78 reviews
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Guest favourite
Home in Fraser
New Winter Park Townhouse with Great Views!
4 bedrooms, 5 beds, 3.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Apartment in Winter Park
10 Minute Walk to the Winter Park Gondola 6 beds.
3 bedrooms, 6 beds, 2.5 bathrooms
15–20 Oct
4.94 out of 5 average rating, 69 reviews
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Flat in Winter Park
Riverside Condo with Pool & Hot Tub Access!
3 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
New place to stay
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Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
New place to stay
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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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Luxe
Townhouse in Winter Park
Lakota SkiRenity | Private Hot Tub
3 bedrooms, 6 beds, 3.5 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Fraser
Spruce Ridge Villa 714H - Great Views - Bunk Room
3 bedrooms, 5 beds, 3 bathrooms
5–10 Oct
5.0 out of 5 average rating, 15 reviews
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Superhost
Apartment in Fraser
Meadow Ridge Retreat | Near Winter Park
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
New place to stay
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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
Apartment in Winter Park
Condo w/ Mountain Views in Heart of Downtown!
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 93 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