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Search results; Over 1,000 homes in Winter Park

Guest favourite
Apartment in Winter Park
Cozy mountain retreat in downtown Winter Park
1 bedroom, 3 beds, 1 private bathroom
9–14 Sept
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4.94 out of 5 average rating, 164 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
Home in Fraser
New Winter Park Townhouse with Great Views!
4 bedrooms, 5 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 6 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
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
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
Townhouse in Winter Park
Luxury Winter Park Retreat with Private Hot Tub
3 bedrooms, 4 beds, 4 bathrooms
20–25 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Townhouse in Winter Park
Luxury Ski in/Ski out town home, private hot tub
4 bedrooms, 5 beds, 4.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 63 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
Home in Winter Park
Downtown WP Penthouse 221 I Private Hot Tub I View
3 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Guest suite in Fraser
The Mountains are calling!
1 queen bed, 1 bathroom
13–18 Sept
4.92 out of 5 average rating, 702 reviews
Home in Winter Park
The Grand Den | Rooftop Spa, Garage & Superb Views
4 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Apartment in Winter Park
New Condo Downtown Winter Park-Close to the Slopes
2 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Winter Park
Duplex In town! Views! PrvtHottub,2Cgarage,Sleeps9
3 bedrooms, 6 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Winter Park
Mountain Escape Minutes From WP | Hot Tub Access
3 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
4.92 out of 5 average rating, 72 reviews
Top guest favourite
Apartment in Winter Park
Cozy DT condo mins from slopes
2 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 105 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
Après Above It All | Rooftop Hot Tub I Walkable
4 bedrooms, 5 beds, 3.5 bathrooms
15–20 Sept
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