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
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
Arrow at Winter Park Unit 202
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 39
Prepare to immerse yourself in the pinnacle of mountain living! This exquisitely renovated 3-bedroom condominium serves as the ideal resort escape, featuring contemporary furnishings, state-of-the-art appliances, stunning river vistas and ample space for all to relish a mountain retreat.The main open-concept design showcases hardwood flooring and l
Hot HOT 12
Winter Park Place #1
Condo - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 39
Welcome to our luxury townhome Arrow 256.This exquisite townhome offers breathtaking mountain views, private outdoor rooftop hot tub, 4 interior levels, open floor plan and a bunk room for the smaller ones with an arcade game, 2 car garage parking and will comfortably accommodate up to 9 guests.The main level (second floor of the unit) is perfect f
Arrow At Winter Park Unit 256
Townhome
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Welcome to our home at 500 North Lupine! This charming townhome in Fraser is perfect for pet owners and provides a serene rental experience while being close to a variety of outdoor activities year-round. Located at the Cabins of Porcupine Ridge, this spacious 3-bedroom unit can host up to 8 guests, featuring breathtaking views and an open floor pl
500 North Lupine
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 99
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 15
Timber Lake 341
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 23
Welcome to our home at 1459 Prairie Sage Road.Your Perfect Mountain Getaway Awaits. Looking for the ideal Colorado retreat? This beautifully maintained 5-bedroom mountain home sits on nearly 10 private acres with jaw-dropping views of the Winter Park Ski Area, the Continental Divide, and the Indian Peaks. The home is thoughtfully designed for comfo
Hot HOT 13
1459 GCR 5221
Private Vacation Home
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests
Welcome to our home at 233 Tabernash Drive.Uncover a delightful mountain getaway situated on 3 private acres in the Winter Park Highlands, providing an exceptional level of privacy with no visibility to adjacent residences, complemented by an aspen grove that serves as a natural barrier from the road. The property boasts ample outdoor space and bre
233 Tabernash Drive
Private Vacation Home -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 5 1
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
128 GCR 4034
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 15
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
Hot HOT 11
74 Alder Brook
Private Vacation Home -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 5 49
This rental townhome, which is pet-friendly, provides a peaceful retreat with two spacious living areas that can comfortably host up to 10 guests. It has been renovated to offer all the amenities needed for a fantastic vacation experience.The main level features a spacious living area with furniture, gas fireplace, flat screen TV and large windows
67 Fireweed 27A
Townhome - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 62
Welcome to our home at 238 Night Hawk.The perfect mountain home getaway - outdoor private hot tub, 4 bedroom 3.5-bath and comfortably sleeps 12, vaulted ceilings, private deck with views, ideal for a large family or two families traveling together and located in a wonderful neighborhood near the Granby Ranch Resort and centrally located to all the
Hot HOT 10
238 Night Hawk Home
Private Vacation Home -
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 1
A remarkably spacious 4 bedroom townhome in downtown Winter Park, located at the Arrow development, offers stunning views from the private rooftop hot tub of the Continental Divide. Its prime location on Main Street ensures convenient access to summer festivals at the Rendezvous Event Center as well as a short stroll to various restaurants, nightl
Arrow At Winter Park Unit 280
Townhome -
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 5

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