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 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 11
40 Crescentview Lane
40 Crescentview Lane
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 4
Located in the quiet residential neighborhood of Fraser, this home is 6 miles from the Winter Park Ski Resort and the home is situated on a 0.8-acre lot and provides easy access to the free town shuttle that stops across the street. This vacation getaway has been renovated into a luxurious, high-end themed vacation home with comforts and entertain
Hot HOT 23
59 Jabberwocky Home
59 Jabberwocky Home
Private Vacation Home -
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 5 11
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
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 15
55 Campfire - Rendezvous
55 Campfire - Rendezvous
Private Vacation Home - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.8 17
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 11
25 Discovery Lane - Rendezvous
25 Discovery Lane - Rendezvous
Private Vacation Home -
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.7 12
This spacious townhome offers 1596 square feet on two levels and is Pet Friendly! 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 s
Hot HOT 16
45 Reunion Court - Rendezvous
45 Reunion Court - Rendezvous
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.5 2
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
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 15
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
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, 2,077 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 19
12 Yukon Lane Townhome
12 Yukon Lane Townhome
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.8 19
This updated 3 bedroom has bonus bunk room to sleep up to 9 people and how can you not say yes to a rooftop hot tub and is pet friendly for your next downtown Winter Park getaway!A heated garage is an ideal spot to store all your skis, snowboards, bikes, and boots; and 2 cars can be parked in tandem here. Entering the townhouse from the garage, you
Hot HOT 21
Arrow at Winter Park Unit 286
Arrow at Winter Park Unit 286
Townhome - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 4.8 28
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 12
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 great spot for couples (and Pets) 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
Hot HOT 23
Arrow at Winter Park Unit 276
Arrow at Winter Park Unit 276
Townhome - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.7 4

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