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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Apartment in Winter Park
Winter Park Studio: On the River~ Walk Downtown!
Studio, 2 beds, 1 private bathroom
19–24 Oct
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4.98 out of 5 average rating, 438 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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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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Top guest favourite
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 499 reviews
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Featured hotel
Hotel in Winter Park
Gravity Haus Winter Park, Superior king twin trun.
1 bedroom, 1 bathroom
3–8 Oct
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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
WP Resort Villa 509 - Hot Tub - Views - Theatre
4 bedrooms, 6 beds, 4.5 bathrooms
1–6 Oct
New place to stay
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Guest favourite
Flat in Winter Park
Cozy Winter Park Condo - Heart of Town
1 bedroom, 2 beds, 1 bathroom
2–7 Oct
4.95 out of 5 average rating, 22 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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Guest favourite
Townhouse in Winter Park
Modern/Rustic 2-bedroom Townhouse + Bonus Loft
2 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
4.97 out of 5 average rating, 203 reviews
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Superhost
Home in Winter Park
Rocky Mountain Divide
5 bedrooms, 7 beds, 3 bathrooms
6–11 Oct
New place to stay
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Top guest favourite
Flat in Winter Park
Mountain Town Luxury Penthouse
2 bedrooms, 3 beds, 3 bathrooms
20–25 Apr
5.0 out of 5 average rating, 28 reviews
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Guest favourite
Apartment in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 165 reviews
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Top guest favourite
Apartment in Winter Park
Zephyr Ski In/Out at Winter Park - 1/2 Price Tues!
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 60 reviews
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Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 3 bathrooms
6–11 Oct
New place to stay
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Top guest favourite
Flat in Winter Park
NEW Ski In/Out Condo w/ Hot Tub & Balcony
2 bedrooms, 4 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 55 reviews
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Top guest favourite
Apartment in Winter Park
Ski In/Out Sleep 10 LUX ZML Penthouse Low Chemical
3 bedrooms, 7 beds, 3 bathrooms
10–15 Oct
5.0 out of 5 average rating, 21 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
6–11 Oct
4.96 out of 5 average rating, 114 reviews
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Top guest favourite
Apartment in Winter Park
Winter Park Condo on the River: Walk to Downtown!
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 125 reviews