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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds
5–10 Oct
4.92 out of 5 average rating, 78 reviews
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Top guest favourite
Home in Fraser
Mountain Retreat | New Condo | Private Hot Tub
2 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 87 reviews
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Top guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds
18–23 Oct
4.97 out of 5 average rating, 36 reviews
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Guest favourite
Home in Winter Park
Winter Park Pond Chalet 13 - Hot Tub - Views
4 bedrooms, 5 beds
11–16 Oct
4.77 out of 5 average rating, 22 reviews
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Top guest favourite
Guest suite in Fraser
The Mountains are calling!
1 queen bed
11–16 Oct
4.92 out of 5 average rating, 704 reviews
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Guest favourite
Home in Fraser
New Winter Park Townhouse with Great Views!
4 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 6 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
27 Sept – 2 Oct
4.92 out of 5 average rating, 64 reviews
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Top guest favourite
Apartment in Winter Park
Downtown Mtn Oasis + Hot Tubs | Steps to Events
2 bedrooms, 5 beds
20–25 Sept
4.96 out of 5 average rating, 114 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
20–25 Sept
4.91 out of 5 average rating, 11 reviews
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Guest favourite
Apartment in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds
20–25 Sept
4.94 out of 5 average rating, 165 reviews
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Guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds
10–15 Oct
4.97 out of 5 average rating, 36 reviews
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Guest favourite
Home in Winter Park
Lux 8000SQ Ft, 9 BDR, 15 Beds, Hot Tub, Lrg Grps
9 bedrooms, 15 beds
28 Sept – 3 Oct
4.9 out of 5 average rating, 153 reviews
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Top guest favourite
Townhouse in Winter Park
Winter Park Townhome w/ Stunning Slope Views!
3 bedrooms, 6 beds
13–18 Oct
4.94 out of 5 average rating, 163 reviews
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Guest favourite
Apartment in Fraser
Alpine Luxe Loft- Hot Tub, Fireplace, Views, Ski
3 bedrooms, 4 beds
1–6 Nov
4.91 out of 5 average rating, 33 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
15–20 Oct
4.94 out of 5 average rating, 69 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
28 Sept – 3 Oct
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Home in Fraser
Spruce Ridge Villa 714H - Great Views - Bunk Room
3 bedrooms, 5 beds
5–10 Oct
5.0 out of 5 average rating, 15 reviews
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Luxe
Townhouse in Winter Park
Lakota SkiRenity | Private Hot Tub
3 bedrooms, 6 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 7 reviews