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, town homes,  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 45 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
Hot HOT 20
Arrow at Winter Park Unit 202
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 36
This residence is ideally suited for several families or small groups seeking both privacy and a convenient location for their skiing or summer holiday. Notable features of this Winter Park home include stunning mountain views of the Continental Divide and Byers Peak, along with the added benefit of three master suites for enhanced privacy. We bel
Hot HOT 30
Leland Creek Home
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 4.5 16
Experience AMAZING VIEWS! 20 Minutes to Winter Park or Granby Ranch Skiing! at the ultimate mountain getaway at this expansive 4-bedroom sanctuary, offering a blend of opulence and serenity amidst the natural surroundings. Situated a short drive away from Fraser and Winter Park, guests can enjoy easy access to various amenities including shops, di
Hot HOT 23
273 Fallen Rock
Private Vacation Home - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 46
Our Fairways townhome is an upscale contemporary getaway situated near the base of Granby Ranch Resort offering lots of amenities, two interior levels and provides guests stunning mountain vistas from a private balcony and plenty of interior space with two living rooms and a private outdoor hot tub and an interior design that is meticulously crafte
Hot HOT 24
100 Fairway Lane
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 3
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
Winter Park Place #1
Condo - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 30
This charming pet-friendly 3-bedroom retreat offers a cozy getaway for up to 8 guests and easy access to downtown Fraser's breweries, restaurants and great year round outdoor activities. A single level condo featuring an open floor plan with a fully equipped kitchen, breakfast bar, dining area, and a comfortable living room with a gas fireplace and
Hot HOT 16
448 Cranmer Unit 103
Condo - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 60
Book your next experience in the ultimate mountain getaway at the Winter Park Hideout in this expansive 5-bedroom sanctuary, offering a blend of opulence and one of a kind amenities and floor plan. Our home is located in Tabernash offering guests a perfect home base to explore all the outdoor activities and local attractions as it is centrally loca
Hot HOT 19
349 Ridge Road
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.5 2
This recently built 5-bedroom corner unit at the Arrow townhome development provides unique amenities such as stunning views from the private hot tub overlooking the Continental Divide and hillside scenery of the Rendezvous Event Center for music festivals in downtown Winter Park, as well as partial views of Winter Park Resort from the spacious roo
Hot HOT 28
Arrow at Winter Park Unit 284
Townhome -
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 37
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 23
Timber Fox Building C Unit 3404
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 5
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
Hot HOT 19
Antlers At Lakota 406
Townhome -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 12
Our Hideaway Station unit 202 is a perfectly situated 2 bedroom condo in the heart of downtown Winter Park and walking distance to a number of restaurants, shops, activities and the free town shuttle stops in front of the complex on Main Street. This stunning condo offers breathtaking mountain views from the private deck and an ambiance that blends
Hot HOT 18
Hideaway Station E #202
Condo - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 12
This vacation rental boasts an ultra-contemporary design and elegant furnishings, featuring 1,764 square feet of living space across two levels. Numerous expansive windows allow guests to admire the stunning mountain views. The expansive living room boasts a southern exposure, offering breathtaking views of stunning sunsets. It provides direct ac
Hot HOT 22
47 Lookout Point - Rendezvous
Private Vacation Home -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 23

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