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Search results; Over 1,000 homes in Winter Park

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Guest favourite
Flat in Winter Park
Cozy Winter Park Condo - Heart of Town
1 bedroom, 2 beds, 1 private bathroom
29 Sept – 4 Oct
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4.95 out of 5 average rating, 22 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
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
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
Flat in Winter Park
Winter Park Ski Paradise
3 bedrooms, 6 beds, 3 bathrooms
2–7 Oct
5.0 out of 5 average rating, 6 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
11–16 Oct
4.97 out of 5 average rating, 36 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
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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Top guest favourite
Home in Fraser
Mountain Retreat | New Condo | Private Hot Tub
2 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
4.97 out of 5 average rating, 87 reviews
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Top guest favourite
Flat in Winter Park
Hip Ski Pad • Hot Tub • Steps to Downtown
2 beds, 1 bathroom
20–25 Sept
4.85 out of 5 average rating, 39 reviews
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Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds, 3 bathrooms
5–10 Oct
4.92 out of 5 average rating, 78 reviews
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Guest favourite
Apartment in Winter Park
Luxe 4BR Winter Park Retreat w/ Private Hot Tub
4 bedrooms, 5 beds, 3 bathrooms
5–10 Oct
4.91 out of 5 average rating, 68 reviews
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Top guest favourite
Apartment in Winter Park
The Rustic Moose
2 bedrooms, 6 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 71 reviews
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Guest favourite
Flat in Winter Park
Winter Park 2 bedrooms Corner Unit w outdoor patio
2 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 32 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
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 499 reviews
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Top guest favourite
Apartment in Winter Park
Ski In/Ski Out - Modern Cozy Condo in Winter Park
2 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 249 reviews
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Guest favourite
Guest suite in Winter Park
New Look! Breakfast, Hot Tub & No Host fee!
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.84 out of 5 average rating, 473 reviews
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Guest favourite
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds, 4 bathrooms
10–15 Oct
4.97 out of 5 average rating, 36 reviews