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 30 properties available
This Colorado home is located 2/3 of a mile from main street in downtown Winter Park and 3 miles to the Winter Park Resort in a cozy neighborhood that offers a secluded feel with wonderful mountain views making for an ideal location for one large family or a small group. This newly remodeled mountain vacation home has 2,995 square feet of living s
Hot HOT 12
40 Crescentview Lane
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 4
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
Timber Fox Building B Unit 2102
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
A warm and welcoming interior with hardwood floors, stone fireplace, and plush carpeting in the open floor plan is delightful spot containing a spacious kitchen with stainless steel appliances and granite counter tops, a dining room and living room. Your family will enjoy the extended living area outside on the deck complete with gas grill. The vie
Hot HOT 22
55 Campfire - Rendezvous
Private Vacation Home - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.8 17
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 11
Timber Lake 341
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 9
Plan your escape to this magnificent pet friendly Winter Park Colorado Vacation Home. This spacious home offers all the comforts and amenities needed for a perfect family getaway with 3 bedrooms, 2,790 square feet of living space on 3 levels and minutes away from Winter Park Resort! The main level has an open floor plan encompassing the gourmet ki
Hot HOT 16
12 Yukon Lane Townhome
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 4.8 18
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
This large and beautiful home offers outstanding mountain views and a great rental for peace and quiet that will accommodate 8 people.An open floor plan encompasses the living, dining, kitchen areas as well as half bathroom on the main level. The living room offers a very cozy spot to relax on the comfortable sofa to enjoy the flat screen TV, gas
2002 Lupine Lane
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 3
A beautiful pet friendly townhome is in Fraser offering a quieter rental but still close to all the year-round outdoor activities. This spacious and wonderful townhome at the Cabins of Porcupine Ridge, this 3-bedroom unit offers something for everyone and will sleep up to 8 persons with great views and an open floor plan. On the main level is an op
500 North Lupine
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 26
A great spot for couples wanting to take a break and enjoy downtown Winter Park luxury accommodations in the Arrow Townhomes. This unit will sleep up to 10 people in this 3 bedroom unit and it offers the best views with a private hot tub amenity for your next Winter Park vacation.A private garage where 2 cars can be parked in tandem is on the lowe
Hot HOT 16
Arrow at Winter Park Unit 276
Townhome - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 3
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 21
Arrow at Winter Park Unit 248
Townhome -
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 12
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 18
67 Fireweed 27A
Condo - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.7 14
An ultra-modern and beautifully appointed townhome has 1,764 square feet of living space on two levels and lots of large windows to marvel at the magnificent mountain views from this vacation rental. A spacious living room is south facing for spectacular sunsets, access to the private deck with BBQ grill, space to relax and the private hot tub. Al
Hot HOT 11
47 Lookout Point - Rendezvous
Private Vacation Home -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 7

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