Winter Park Luxury Vacation Rentals

Explore Luxury Lodging in Winter Park, CO

Looking to make unforgettable and enduring memories during your upcoming mountain getaway? Search no further, reserve one of our opulent Winter Park rentals today; providing guests with something extraordinary and distinctive that is bound to be unforgettable! Stay Winter Park is delighted to offer a splendid array of vacation homes, cabins,  townhomes, and condos that surpass your typical vacation rental with numerous additional touches and details to enhance your stay right from the beginning.

Our deluxe rentals are all recently built and showcase top-of-the-line appliances, granite countertops, private garages, flat screen HDTVs, and more! Many of these Winter Park rentals also boast their own private hot tub and a spacious deck with stunning mountain views. Some even feature large communal areas for group gatherings. Numerous properties are conveniently situated near local attractions and activities, while others are tucked away off the beaten path, providing guests with a sense of seclusion.

Moreover, several properties in this luxury collection are ideal for corporate or executive retreats, family reunions, or weddings in Winter Park. We offer customized quotes for groups to accommodate your travel and event requirements, along with recommendations for local vendors offering additional services. Don't hesitate to reach to our Group Reservations team today. We encourage you to secure a vacation of a lifetime at any of these luxurious properties, explore all the rentals in this collection, and prepare to embark on an unforgettable journey.


Properties Available 48 properties available
Welcome to our home at 200 Quill Court! This lovely 4-bedroom vacation retreat is nestled in Fraser at the Cabins of Porcupine Ridge. With a thoughtfully designed interior, two cozy living spaces, a private outdoor hot tub on the patio, a dedicated laundry room, and garage parking, this home can comfortably accommodate up to 9 guests across three s
Hot HOT 12
200 Quill Court
Private Vacation Home -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 9 guests
Rating 5 1
Reserve your upcoming visit to Winter Park in this opulent two bedroom unit at Pine Tree Plaza. Situated on Main street in the heart of downtown, you will have convenient access to dining, shopping, nightlife, summer festivals and the complimentary town shuttle - our condominium is perfect for families or small groups looking to experience the are
Hot HOT 14
303 Pinetree
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 7
Beautiful new construction Modern townhome with private hot tub and fire pit on large roof top deck in Winter Park! 3 bedroom 3 bathroom unit with a spacious common area and a flex space that can be used as a fourth bedroom/second living/office. Walking distance to concerts, restaurants, and shops. Private Hot Tub, fire pit and bbq grill island on
Hot HOT 305
17 Ski Idlewild
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 16
Welcome to our home at 74 Alder Brook! Step into the luxury of this stunning, spacious home that’s just been built, perfect for creating unforgettable family memories during your vacation in Fraser. Picture yourself soaking in the awe-inspiring mountain views from your private patio, enjoying the cozy warmth of in-floor radiant heating, and parking
74 Alder Brook
Private Vacation Home -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 5 49
This Bear Crossing three-bedroom townhome features a remarkably spacious interior, high-quality finishes throughout, and a multi-level layout. Spanning 2,000 square feet, it provides ample room for a group of eight to spread out, enjoy the nearby outdoor activities, and admire the stunning mountain views from the large windows in the main living ro
Bear Crossing 435
Townhome -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 1
Welcome to your cozy mountain retreat at Timber Fox Building C Unit 3404, nestled in the heart of Winter Park. This luxurious 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and elegance, ideal for families or groups of friends seeking a memorable getaway.Step inside to discover a thoughtfully designed living space, complete with a mo
Hot HOT 15
Timber Fox Building C Unit 3404
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 9
Escape to the mountains at this splendid, newly constructed residence boasting unforgettable mountain and lake views with a high-end interior designed 5 bedroom home that will sleep up to 10. This extraordinary mountain home offers beatle-kill hardwood flooring on the main level, accented by hand-hewn wooded plank ceilings and custom cabinetry.On
Hot HOT 14
128 GCR 4034
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 15
This tri-level townhome offers an abundance of natural light and generous square footage, making it the perfect vacation rental for families or individuals seeking spacious accommodations.The primary level features a spacious entryway adorned with tiled flooring, providing ample space for storing jackets and coats. This area also offers convenient
Hot HOT 10
Timber Lake 341
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 23
Visitors can appreciate the main floor living room as the focal point of this stunning townhome, with its large expansive windows providing an unforgettable view of the ski resort, and the vaulted ceilings create an even more spacious feel. Relax on the comfortable sofas, watch TV or warm your toes in front of the gas fireplace. The adjacent din
Antlers At Lakota 406
Townhome -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 12
The ski resort can be admired through the expansive windows and from the rooftop deck, while the vaulted ceilings enhance the spaciousness of the area. Relax on the comfortable sofas, watch TV or cozy up by the gas fireplace. The dining area and kitchen are conveniently located nearby, allowing the cook to engage with the group. The kitchen boasts
Arrow at Winter Park Unit 248
Townhome -
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 35
Explore our brand new exquisite 2-bedroom, 2-bathroom condominium located in the center of downtown Winter Park! This flawless residence showcases top-notch contemporary aesthetics and comes fully furnished, perfect for your own use or as a vacation rental. Conveniently located near the main street, this unit provides easy access to Winter Park's d
Hot HOT 11
Arrow at Winter Park Unit 202
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 39
This elegant slopeside mountain sanctuary with a private hot tub is an easy 5-minute walk to the Winter Park Resort. The Ski Haus is an exquisitely designed residence that captures the artistic and refined elements sought for your upcoming mountain retreat. With 6 bedrooms and 6 ½ bathrooms, it accommodates up to 19 guests, ensuring a comfortable a
Hot HOT 51
Winter Park Ski Haus
Private Vacation Home - Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 19 guests
Rating 5 59

Tell us what you're looking for and someone will contact you with available options.

By providing your phone number, you agree to receive text messages from our company. Message and data rates may apply. Message frequency varies.
I agree