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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Apartment in Winter Park
Walk to Shops & Dining! Winter Park Condo w/ Pool
2 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
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5.0 out of 5 average rating, 55 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 Winter Park
Top Floor Condo Steps From Free Shuttle w/Hot Tub
2 bedrooms, 2 queen beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 289 reviews
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Top guest favourite
Flat in Winter Park
Mountain Town Luxury Penthouse
2 bedrooms, 3 beds, 3 bathrooms
14–19 Oct
5.0 out of 5 average rating, 27 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
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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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
Flat in Fraser
3 BD/3 BA + BunkRoom + Top Floor Spa + MTN Views
4 bedrooms, 6 beds, 3 bathrooms
18–23 Oct
4.96 out of 5 average rating, 106 reviews
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Top guest favourite
Apartment in Winter Park
Cozy Winter Park Riverfront Studio~ Walk Downtown
2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 121 reviews
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Guest favourite
Apartment in Winter Park
Close to everything, AC in Downtown with Views!
2 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 13 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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Luxe
Home in Winter Park
Fish, Raft, Hike. Then Home to a Rooftop Soak
5 bedrooms, 8 beds, 5.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Fraser
Mountain Retreat | New Condo | Private Hot Tub
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 87 reviews
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Top guest favourite
Townhouse in Winter Park
Winter Park Townhome w/ Stunning Slope Views!
3 bedrooms, 6 beds, 2.5 bathrooms
13–18 Oct
4.94 out of 5 average rating, 163 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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Apartment in Winter Park
Stylish 2 BR Condo with Hot Tub and Ski Locker
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
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Guest favourite
Home in Winter Park
Luxurious Mountain Home near Downtown Winter Park!
7 bedrooms, 17 beds, 6.5 bathrooms
24–29 Sept
4.89 out of 5 average rating, 87 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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Top guest favourite
Apartment in Winter Park
Luxury Condo on Main Street - Winter Park, CO
2 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 82 reviews