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Search results; Over 1,000 homes in Winter Park

Top guest favourite
Home in Winter Park
Pool Access & Mtn View! Luxe WP Cabin, Near Trails
3 bedrooms, 3 beds, 2 private bathrooms
21–26 Sept
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4.99 out of 5 average rating, 156 reviews
Top guest favourite
Townhouse in Winter Park
The Camping Bear
4 bedrooms, 7 beds, 3 bathrooms
14–19 Sept
4.92 out of 5 average rating, 78 reviews
Guest favourite
Apartment in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds, 1 bathroom
9–14 Sept
4.94 out of 5 average rating, 164 reviews
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, 220 reviews
Guest favourite
Apartment in Winter Park
Beautiful Condo at Winter Park!
1 bedroom, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 105 reviews
Top guest favourite
Apartment in Winter Park
Winter Park Studio: On the River~ Walk Downtown!
2 beds, 1 bathroom
15–20 Sept
4.98 out of 5 average rating, 434 reviews
Superhost
Apartment in Winter Park
WP Mountain Retreat • 3BR/2BA • 3 Hot Tubs & Pool
3 bedrooms, 7 beds, 2 bathrooms
12–17 Sept
4.87 out of 5 average rating, 122 reviews
Guest favourite
Cabin in Winter Park
Cabin w/ Deck- Bike & HikeTrails & Downtown- RMNP
5 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
4.86 out of 5 average rating, 21 reviews
Superhost
Cabin in Winter Park
Cozy Cabin in Perfect Location
2 beds, 1 bathroom
7–12 Oct
4.84 out of 5 average rating, 653 reviews
Luxe
Home in Winter Park
Ski In Out Chalet 277 - Hot Tub - Great Views
4 bedrooms, 13 beds, 4.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 72 reviews
Guest favourite
Flat in Winter Park
Ski in / Ski out at Winter Park - pool & hot tub
2 beds, 1 bathroom
24–29 Sept
4.95 out of 5 average rating, 19 reviews
Guest favourite
Apartment in Winter Park
Prime location, amazing views, stylish, sleeps 7
2 bedrooms, 5 beds, 2 bathrooms
9–14 Sept
4.87 out of 5 average rating, 119 reviews
Top guest favourite
Home in Fraser
Spacious Cabin with Views • Location • Hot Tub
3 bedrooms, 7 beds, 3.5 bathrooms
9–14 Sept
4.95 out of 5 average rating, 174 reviews
Top guest favourite
Apartment in Winter Park
Top Floor Condo Steps From Free Shuttle w/Hot Tub
2 bedrooms, 2 queen beds, 2 bathrooms
13–18 Sept
4.93 out of 5 average rating, 287 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
Top guest favourite
Apartment in Winter Park
New Condo Downtown Winter Park-Close to the Slopes
2 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Apartment in Winter Park
Luxe 4BR Winter Park Retreat w/ Private Hot Tub
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
4.91 out of 5 average rating, 67 reviews
Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds, 4.5 bathrooms
9–14 Sept
New place to stay
Top guest favourite
Home in Winter Park
Luxury Winter Park HomeHotTub*Majestic View*Resort
4 bedrooms, 9 beds, 4 bathrooms
13–18 Sept
4.97 out of 5 average rating, 36 reviews