Luxury Properties

Luxury Vacation Rentals in Winter Park CO

Looking to create unforgettable and lasting memories on your next mountain vacation? Look no further, book one of our luxurious Winter Park rentals today; offering guests something special and unique and sure to be memorable! Stay Winter Park is pleased to provide a wonderful collection of vacation homes, town homes, condos that go above and beyond your traditional vacation rental with many extras touches and finishes to make your stay even more enjoyable right from the start.

Our luxury rentals are all newly constructed and feature high-end appliances, granite counter tops, private garages, flat screen HDTVs, and more! Many of these rentals in Winter Park also have their own private hot tub and a large deck providing beautiful mountain views. Others include large group gathering spaces. Many are conveniently located near area attractions and activities while others are truly off the beaten path offering guests seclusion from the world.

Additionally, many of the properties in this luxury collection are perfect if you are planning a corporate or executive retreat, family gathering, or wedding in Winter Park. We offer groups customized quotes for your travel and meeting needs, including local vendor recommendations for additional services. Be sure to contact our Group Reservations team  today. We invite you to reserve a vacation of a lifetime with any of these luxury properties, browse all the rentals in this collection and get ready to experience the trip of a lifetime.


Properties Available 31 properties available
A wonderful location in Fraser, this Mountain Terrace private home offers a 2 car garage parking and spacious interior with distinctive touches provided by great architectural design and beautifully decorated throughout.A warm and welcoming open floor plan greets you with vaulted ceilings to accentuate the large windows, hardwood floors, stone gas
Hot HOT 15
751 Mountain Terrace
Private Vacation Home -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 5 2
This Bear Crossing town home has very spacious interior, high-end finishes throughout and multi-level floor plan. The 2,000 square feet offers more than enough space for group of eight to spread out and take advantage of the great outdoor activities nearby.A wonderful three bedroom three bathroom town home provides guests a feeling of seclusion bu
Bear Crossing 845
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 4
Escape to Redroc Lodge, an exquisite 5-bedroom, 4-bathroom retreat in the captivating Winter Park Highlands of Tabernash. This 5,300-square-foot sanctuary seamlessly fuses rustic mountain charm with contemporary comforts, offering sweeping Rocky Mountain vistas. With a updated kitchen, inviting living areas, entertainment rooms, and a picturesque o
Hot HOT 17
864 Rainbow The Redroc Lodge
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 15 guests
Rating 5 1
Luxurious, new construction this 3 bedroom unit is in the heart of downtown Winter Park. This Timber Fox has a wonderful view from the private patio of the Winter Park Ski Resort and surrounding forested area – perfect spot to relax, enjoy morning coffee and the BBQ grill.The main open floor plan has hardwood flooring and large expansive windows a
Hot HOT 13
Timber Fox Building B Unit 2102
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
This spacious townhome offers 1596 square feet on two levels. The main level has vaulted ceilings with ceiling fans and the look of a true log cabin in the open floor plan encompassing the living, dining and kitchen areas. A gourmet kitchen offers stainless steel appliances, granite counter tops, solid wood cabinets and extra seating at the breakf
Hot HOT 10
45 Reunion Court - Rendezvous
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.5 2
This newly constructed 5-bedroom end-unit at the Arrow town home complex offer exclusive extras including tip-top views from the private hot tub with the Continental Divide and hillside sights of the Rendezvous Event Center for music festivals in downtown Winter Park, plus peak-a-boo views of Winter Park Resort all from the over-sized rooftop patio
Arrow at Winter Park Unit 284
Townhome -
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.5 12
Tons of light and a lot of square footage in this tri-level town home make it the ideal vacation rental for families or singles looking for lodging that has a lot of space. The main level has a large entryway with tiled flooring to storage your jackets, coats and an excellent spot to access the one car garage, laundry room and bedroom with 2 twin b
Hot HOT 16
Timber Lake 341
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 9
A pet friendly rental townhome offers a great spot to find solitude as well as 2 living area, large enough to accommodate 10 people and has been remodeled with all the comforts for a wonderful vacation.A spacious living on the main level has furniture, gas fireplace, flat screen TV and large windows offering mountain views. You can also access the
Hot HOT 16
67 Fireweed 27A
Condo - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.7 14
After a day of outdoor adventure, come home to relax on the large, comfortable leather sectional sofa surrounded by the luxury of the great room with vaulted ceilings, oversized windows, gas fireplace and 65" flat screen TV with sound bar. Set up a puzzle or board game on the lift-top coffee table from the wide selection of games, toys and books in
71 Alder Brook Homer’s Hideaway
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 17
This home is perfect for multiple families or small groups looking for privacy and a convenient location for their ski trip or summer vacation with some of the exceptional attributes of this Winter Park home are the mountain views of the Continental Divide and Byers Peak plus the added privacy with the three master suites! We think that you will lo
Hot HOT 12
Leland Creek Home
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 14 guests
Rating 4.3 10
Escape to the perfect mountain cabin for your next mountain vacation. This fabulous gathering place is surrounded by 40 acres, only a short 10 minute drive to downtown Winter Park, pet friendly, built off the grid in 1998 encompassing 3,884 square feet and will accommodates up to 11 people.The open space of the family room, dining and kitchen with
Hot HOT 21
Miles Behind Log Cabin
Cabin - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 4.8 26
Hugh expansive windows provide the unforgettable view of the ski resort and the vaulted ceilings make the overall space feel even bigger. Enjoy the comfy sofas to relax, watch TV or warm the toes in front of the gas fireplace. Next to this area, the dining area and kitchen are great for the cook to interact with the rest of the group while prepar
Hot HOT 12
Arrow at Winter Park Unit 248
Townhome -
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 12

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