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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Apartment in Winter Park
2.5 BR Near Winter Park Base & Gondola, Riverfront
3 bedrooms, 6 beds, 2.5 private bathrooms
1–6 Oct
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4.99 out of 5 average rating, 114 reviews
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Townhouse in Winter Park
Yukon Forest Depot | Ski-Hike-Bike-Golf-Fish-Relax
5 bedrooms, 8 beds, 3 bathrooms
1–6 Oct
4.83 out of 5 average rating, 6 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
17–22 Oct
4.87 out of 5 average rating, 124 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
4–9 Oct
5.0 out of 5 average rating, 29 reviews
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Luxe
Home in Winter Park
Sleeps 19 | Winterhaven Estate by AvantStay
11 bedrooms, 16 beds, 8 bathrooms
29 Oct – 3 Nov
4.85 out of 5 average rating, 26 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, 37 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
4–9 Oct
4.78 out of 5 average rating, 23 reviews
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Guest favourite
Cabin in Winter Park
Cozy Cabin in Perfect Location
2 beds, 1 bathroom
7–12 Oct
4.84 out of 5 average rating, 659 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
4–9 Oct
4.88 out of 5 average rating, 221 reviews
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Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds, 4.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 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
1–6 Oct
4.91 out of 5 average rating, 11 reviews
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Guest favourite
Apartment in Winter Park
Homebase Snowblaze
2 beds, 1 bathroom
5–10 Oct
4.88 out of 5 average rating, 260 reviews
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Guest favourite
Home in Winter Park
The Owl's Nest | Private Hot Tub | Game Room
4 bedrooms, 9 beds, 4.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Townhouse in Winter Park
Beautiful Townhome in Downtown Winter Park!
4 bedrooms, 7 beds, 4 bathrooms
8–13 Oct
4.9 out of 5 average rating, 234 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
1–6 Oct
4.92 out of 5 average rating, 64 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
1–6 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Apartment in Winter Park
Cozy DT condo mins from slopes
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 107 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
19–24 Oct
4.94 out of 5 average rating, 72 reviews
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Superhost
Home in Winter Park
WP Resort Villa 509 - Hot Tub - Views - Theatre
4 bedrooms, 6 beds, 4.5 bathrooms
1–6 Oct
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