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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, 437 reviews
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Featured hotel
Hotel in Winter Park
Gravity Haus Winter Park, Superior king twin trun.
1 bedroom, 1 bathroom
1–6 Oct
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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
4.78 out of 5 average rating, 23 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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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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Guest favourite
Apartment in Winter Park
Winter Park Ski Resort - Top Floor
1 bedroom, 1 sofa bed, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 42 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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Guest favourite
Home in Winter Park
Luxurious Mountain Home near Downtown Winter Park!
7 bedrooms, 17 beds, 6.5 bathrooms
25–30 Oct
4.89 out of 5 average rating, 87 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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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
Stylish Studio on Main Street in Winter Park
1 king bed, 1 bathroom
1–6 Oct
4.9 out of 5 average rating, 98 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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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
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
4.86 out of 5 average rating, 22 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
New place to stay
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Luxe
Townhouse in Winter Park
Lakota SkiRenity | Private Hot Tub
3 bedrooms, 6 beds, 3.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 7 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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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
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