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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
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
New Condo Downtown Winter Park-Close to the Slopes
2 bedrooms, 6 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 32 reviews
Superhost
Home in Winter Park
Unbeatable Location Downtown Winter Park W/Hot tub
4 bedrooms, 7 beds, 4.5 bathrooms
11–16 Sept
New place to stay
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, 123 reviews
Top guest favourite
Home in Winter Park
WP Resort Villa 502 - Hot Tub - Bunks - Great View
3 bedrooms, 7 beds, 3.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 27 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
13–18 Sept
4.94 out of 5 average rating, 164 reviews
Superhost
Home in Winter Park
Luxury Emerald Escape | Hot Tub | Ski Shuttle
3 bedrooms, 5 beds, 3 bathrooms
11–16 Sept
New place to stay
Guest favourite
Apartment in Winter Park
Winter Park Condo w/ Fireplace - 4 Mi to Slopes!
2 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Apartment in Winter Park
Private Hot Tub + Free Shuttle | Walk Downtown
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 41 reviews
Guest favourite
Apartment in Winter Park
Prime location, amazing views, stylish, sleeps 7
2 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
4.87 out of 5 average rating, 119 reviews
Top guest favourite
Guest suite in Winter Park
Charming Suite in Old Town Winter Park
1 bedroom, 1 queen bed, 1 bathroom
11–16 Sept
4.98 out of 5 average rating, 499 reviews
Top guest favourite
Apartment in Fraser
Walk to Restaurants! Bring your Fishing Pole!
1 bedroom, 3 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 148 reviews
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
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
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
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
Top guest favourite
Townhouse in Winter Park
Winter Park Townhome w/ Stunning Slope Views!
3 bedrooms, 6 beds, 2.5 bathrooms
14–19 Sept
4.94 out of 5 average rating, 163 reviews