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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Townhouse in Winter park
Modern Cabin w/ Hot Tub & Garage - Minutes to Mtn
2 bedrooms, 3 beds, 2 private bathrooms
15–20 Sept
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4.98 out of 5 average rating, 133 reviews
Guest favourite
Apartment in Winter Park
10 Minute Walk to the Winter Park Gondola 6 beds.
3 bedrooms, 6 beds
15–20 Oct
4.94 out of 5 average rating, 69 reviews
Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds
14–19 Sept
4.92 out of 5 average rating, 78 reviews
Guest favourite
Apartment in Winter Park
One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit
1 bedroom, 2 beds
11–16 Oct
4.88 out of 5 average rating, 221 reviews
Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds
12–17 Sept
4.87 out of 5 average rating, 122 reviews
Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds
10–15 Sept
New place to stay
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds
13–18 Sept
4.94 out of 5 average rating, 72 reviews
Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds
13–18 Sept
4.86 out of 5 average rating, 21 reviews
Guest favourite
Apartment in Winter Park
Prime location, amazing views, stylish, sleeps 7
2 bedrooms, 5 beds
10–15 Sept
4.87 out of 5 average rating, 119 reviews
Guest favourite
Apartment in Winter Park
Luxe 4BR Winter Park Retreat w/ Private Hot Tub
4 bedrooms, 5 beds
5–10 Oct
4.91 out of 5 average rating, 67 reviews
Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds
12–17 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Apartment in Winter Park
New Condo Downtown Winter Park-Close to the Slopes
2 bedrooms, 6 beds
10–15 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Flat in Winter Park
Hip Ski Pad • Hot Tub • Steps to Downtown
2 beds
20–25 Sept
4.85 out of 5 average rating, 39 reviews
Top guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds
13–18 Sept
4.97 out of 5 average rating, 36 reviews
Superhost
Cabin in Winter Park
Cozy Cabin in Perfect Location
2 beds
7–12 Oct
4.84 out of 5 average rating, 653 reviews
Top guest favourite
Townhouse in Winter Park
Winter Park Townhome w/ Stunning Slope Views!
3 bedrooms, 6 beds
14–19 Sept
4.94 out of 5 average rating, 163 reviews
Guest favourite
Home in Winter Park
Downtown WP Penthouse 221 I Private Hot Tub I View
3 bedrooms, 7 beds
13–18 Sept
4.9 out of 5 average rating, 10 reviews
Guest favourite
Flat in Winter Park
Ski in / Ski out at Winter Park - pool & hot tub
2 beds
24–29 Sept
4.95 out of 5 average rating, 19 reviews
Guest favourite
Townhouse in Winter Park
Luxury Ski in/Ski out town home, private hot tub
4 bedrooms, 5 beds
13–18 Sept
4.92 out of 5 average rating, 63 reviews