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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 bed, 1 private bathroom
14–19 Sept
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4.98 out of 5 average rating, 499 reviews
Guest favourite
Home in Winter Park
WP Resort Villa 402 - Hot Tub - Arcade - Views
3 bedrooms, 8 beds, 3.5 bathrooms
20–25 Sept
4.85 out of 5 average rating, 41 reviews
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
Guest favourite
Home in Winter Park
Downtown WP Penthouse 221 I Private Hot Tub I View
3 bedrooms, 7 beds, 3 bathrooms
14–19 Sept
4.91 out of 5 average rating, 11 reviews
Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds, 4.5 bathrooms
14–19 Sept
New place to stay
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
Top guest favourite
Apartment in Winter Park
The Rustic Moose
2 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 71 reviews
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
Top guest favourite
Flat in Winter Park
Modern New build ski in/out. 1br + den.
1 bedroom, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 48 reviews
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, 247 reviews
Guest favourite
Townhouse in Winter Park
Cozy Mountain Cabin in the Heart of Winter Park
3 bedrooms, 6 beds, 2.5 bathrooms
14–19 Sept
4.82 out of 5 average rating, 192 reviews
Top guest favourite
Apartment in Winter Park
Ski-In Ski-Out Zephyr Mtn Lodge Condo w/ Hot Tub
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.91 out of 5 average rating, 279 reviews
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
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
Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
New place to stay
Top guest favourite
Apartment in Winter Park
Ski In/Out Sleep 10 LUX ZML Penthouse Low Chemical
3 bedrooms, 7 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 20 reviews
Luxe
Townhouse in Winter Park
Lakota SkiRenity | Private Hot Tub
3 bedrooms, 6 beds, 3.5 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Fraser
Spacious Cabin with Views • Location • Hot Tub
3 bedrooms, 7 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 174 reviews
Top guest favourite
Home in Fraser
Spruce Ridge Villa 714H - Great Views - Bunk Room
3 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 15 reviews