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Search results; Over 1,000 homes in Winter Park

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Top guest favourite
Flat in Winter Park
Luxury Winter Park Studio*PrivHotTub*Majestic View
1 bedroom, 1 bed, 1 private bathroom
15–20 Nov
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4.97 out of 5 average rating, 135 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
Home in Winter Park
Penthouse Cozy Condo Winter Park
3 bedrooms, 3 beds, 3 bathrooms
24–29 Sept
5.0 out of 5 average rating, 9 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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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
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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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
Flat in Winter Park
Mountain Condo w/ Hot Tub | Walk to Town | Ski Bus
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 22 reviews
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Guest favourite
Apartment in Winter Park
Homebase Snowblaze
2 beds, 1 bathroom
20–25 Sept
4.88 out of 5 average rating, 260 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
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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Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
New place to stay
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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 Creekside Chalet with Hot Tub
4 bedrooms, 8 beds, 3 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 177 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
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
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds, 3 bathrooms
19–24 Sept
4.86 out of 5 average rating, 22 reviews