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
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 14
Timber Lake 341
Townhome -
$340.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 9
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 11
Antlers At Lakota 406
Townhome -
$424.00 - $826.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 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
Arrow at Winter Park Unit 248
Townhome -
$457.00 - $709.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 12
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 12
59 Jabberwocky Home
Private Vacation Home -
$310.25 - $667.25 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 5 11
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 13
25 Discovery Lane - Rendezvous
Private Vacation Home -
$665.00 - $1,040.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 4.7 12
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
52 Timber Circle Selah Vista Lodge
Cabin -
$1,500.00 - $2,280.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 5 3
Discover our new stunning 2-bedroom, 2-bathroom condo in the heart of downtown Winter Park! This immaculate unit features high-quality modern design and is offered fully furnished, ready for your enjoyment or as a vacation rental. Situated just off the main street, you'll have easy access to Winter Park's dining and entertainment. With 9-1/2 ft cei
Hot HOT 16
Arrow at Winter Park Unit 202
Condo -
$289.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 1
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
$390.00 - $671.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 16
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 -
$484.00 - $844.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.5 12
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 11
Arrow at Winter Park Unit 276
Townhome - Pet Friendly
$374.00 - $644.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 3
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
47 Lookout Point - Rendezvous
Private Vacation Home -
$565.00 - $940.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 7
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
492 Golf Course Circle
Private Vacation Home -
$1,500.00 - $2,280.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 16 guests
Rating 5 7

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