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.

Search Other Popular Vacation Rental Categories:

Downtown Winter Park Rentals, Private Homes, Winter Park Cabins, Base Village: Ski in Ski Out Lodging, Condo Complexes

Properties Available 31 properties available
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
Hot HOT 13
Arrow at Winter Park Unit 284
Arrow at Winter Park Unit 284
Townhome -
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.6 13
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 16
Leland Creek Home
Leland Creek Home
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 4.3 10
The house is immaculately furnished and equipped with every conceivable convenience and comfort in mind. Occupying 3 levels and offering 7 bedrooms, 8 bathrooms and a heated living space of 9,649 square feet, the home can sleep 16 people easily, making it a perfect vacation venue at any time of the year for large families, family gatherings or reun
Hot HOT 10
492 Golf Course Circle
492 Golf Course Circle
Private Vacation Home -
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 16 guests
Rating 5 7
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
Timber Fox Building B Unit 2102
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 2
Guests will enjoy the focal point of this beautiful townhome on the main floor living room offering huge 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, th
Hot HOT 15
Antlers At Lakota 406
Antlers At Lakota 406
Townhome -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 3
A warm and welcoming interior greets you at the front door entrance filled with distinctive touches including hardwood floors, stone fireplace, stunning views from the private deck surrounded by great architectural design and thoughtful planning. Rare find in Winter Park - 4 bedrooms and 4 bathrooms - this Rendezvous cabin offers one of the best va
Hot HOT 12
25 Discovery Lane - Rendezvous
25 Discovery Lane - Rendezvous
Private Vacation Home -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.7 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 14
67 Fireweed 27A
67 Fireweed 27A
Condo - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 15
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
40 Crescentview Lane
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 4
A wonderful and spacious home - Pet Friendly and more! 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 ta
Hot HOT 14
71 Alder Brook Homer’s Hideaway
71 Alder Brook Homer’s Hideaway
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 17
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
Hot HOT 13
500 North Lupine
500 North Lupine
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 26
This wonderful, spacious 3-bedroom cabin offers 2 living rooms, private decks with spectacular mountain views and is the perfect location for a vacation in the Winter Park/Fraser area. PLEASE NOTE: This is a pet friendly home but will only allow for 1 pet. The main level is the focal point of the cabin and is one story up from the entrance. Enjoy
80 Moosehorn Ct - Rendezvous
80 Moosehorn Ct - Rendezvous
Cabin - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 4.8 7
This luxurious log home boasts 6 bedrooms, home theater, pool table room, outdoor hot tub, decks galore to step outside and enjoy the scenery. Three levels of space with 6700 square feet to find your own quiet place or to bring everyone together. Pristine views from this top of the peak Colorado home situated in downtown Winter Park in the exclus
Hot HOT 10
52 Timber Circle Selah Vista Lodge
52 Timber Circle Selah Vista Lodge
Cabin -
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 5 3

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