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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Apartment in Winter Park
Top Floor Condo Steps From Free Shuttle w/Hot Tub
2 bedrooms, 2 beds, 2 private bathrooms
20–25 Sept
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4.93 out of 5 average rating, 289 reviews
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Guest favourite
Home in Winter Park
Downtown WP Condo 2404 - Hot Tub - Views - Firepit
2 bedrooms, 3 king beds, 2 bathrooms
30 Sept – 5 Oct
4.95 out of 5 average rating, 39 reviews
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Guest favourite
Apartment in Winter Park
One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.88 out of 5 average rating, 221 reviews
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Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds, 3 bathrooms
19–24 Sept
4.86 out of 5 average rating, 22 reviews
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Top guest favourite
Apartment in Winter Park
The Rustic Moose
2 bedrooms, 6 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 71 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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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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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
Flat in Winter Park
Hip Ski Pad • Hot Tub • Steps to Downtown
2 beds, 1 bathroom
20–25 Sept
4.85 out of 5 average rating, 39 reviews
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Top guest favourite
Apartment in Winter Park
Top floor, larger 1 bedroom in Winter Park Village
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 164 reviews
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Guest favourite
Apartment in Winter Park
Prime location, amazing views, stylish, sleeps 7
2 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.87 out of 5 average rating, 119 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
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
Flat in Winter Park
Modern New build ski in/out. 1br + den.
1 bedroom, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 48 reviews
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Guest favourite
Apartment in Winter Park
Homebase Snowblaze
2 beds, 1 bathroom
20–25 Sept
4.88 out of 5 average rating, 260 reviews
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Top guest favourite
Apartment in Winter Park
Private Hot Tub + Free Shuttle | Walk Downtown
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 41 reviews
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Guest favourite
Home in Winter Park
Downtown WP Penthouse 221 I Private Hot Tub I View
3 bedrooms, 7 beds, 3 bathrooms
17–22 Sept
4.91 out of 5 average rating, 11 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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Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 3 bathrooms
17–22 Sept
New place to stay