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Aspen Luxury Holiday Rentals

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    Travellers to Aspen are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    31 Matching Rentals in AspenView all 207 rentals
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    Warm and inviting Swiss Chalet awaits, just outside the downtown core. The split level design and open floor plan incorporates three living levels and four bedroom suites. Glimpse Independence Pass and the glades of Aspen Mountain from the sunny outdoor entertainment area off the living /dining...
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    Aspen, Colorado 81611
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
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    About this property
    Beautifully understated modern design meets the high drama of the Rockies. Set in the heart of downtown Aspen, this luxury Colorado vacation rental is backed by a rugged, forested slope and has incredible views of Aspen Mountain. Four bedrooms and well-appointed, state-of-the-art interiors make the...
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    Aspen, Colorado 81611
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Hyatt Grand Aspen apartment description HAYATT AT ITS BEST... penthouse unit huge size for dinning and party. 3 huge king bedrooms with onsuite bath. huge kitchen very cozy. center of town. Best unit in the property with 2 private jacuzzi's one for mom and dad and another for the kids.What's...
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    About this property
    The Top of the Village Condominiums by Destination Residences offer the perfect retreat in both summer and winter! Creating a sense of seclusion and tranquility, these ski-in/ski-out residences provide spectacular views of Snowmass Mountain. The on-site, full-service front desk, concierge service,...
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    Aspen, Colorado 81611
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Enjoy the convenience of residing slope side at Aspen Highlands with free shuttle service to town. Aspen Highlands, the locals’ favorite mountain, is crowned by the legendary Highland Bowl. Offering two and three bedroom luxury residences with fully equipped kitchens and the famous Ritz Carlton...
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    About this property
    Large Executive home perfect for two families or large groups. This home is designed for entertaining with a large open living area, large wet bar in main living area, Gourmet Kitchen, 3 master suites, large study/media room, expansive yard, AC, and outstanding views from the 3 decks or outdoor hot...
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    Aspen, Colorado 81611
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    About this property
    These newly built Enclave Town Homes offer the finest in elegant accommodations in downtown Aspen. This property features 2 master suites with Jacuzzi's, steam showers, and fireplaces in each suite. Hot Tub. Additional amenities: Full Kitchen Booking Fee - Resortia: 4.4000 SL Fee: 0.4000
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    Aspen, Colorado 81611
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • Skiing: Property Is In A Ski Resort
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    • Mountain Views
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hyatt Grand in Aspen, Colorado is well known for its stunning beauty and legendary charm and is the perfect setting for your vacation. Beautiful residence to be your home while on your vacation. Sleep in these luxurious beds with down filled comforters on top of you while you look out your window...
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    Aspen, Colorado 81611
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    About this property
    This stunning custom home was designed by famed Aspen architect Dave Gibson and features 16 foot ceilings, hardwood floors, radiant heat, 450 bottle wine room, 3 fireplaces, two 50 inch plasma TVs, media room, wet bar, 2 car heated garage, AC, steam shower, jacuzzi, hot tub, granite, and top of the...
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    Aspen, Colorado 81611
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Historic Aspen West End Home with True Aspen Charm (203146)1 / 24
    (1)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Reviewed 27 January 2018
    We felt like locals! We loved the west end location with lots of trees and flowers. We took morning walks in the beautiful neighborhood and hikes in the nearby trails and...
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    About this property
    Lovely 6,000 square foot West End home in quiet Residential neighborhood. This classic West End home features 5 bedrooms, each with their own bathroom, 2 master suites, large gourmet kitchen, large great room with gas fireplace, library, family room with piano, 2 large deck with views of shadow...
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    Aspen, Colorado 81611
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Opportunity to rent from owner a luxury 2 bedroom ski-in/ski-out condo in Aspen Highlands, celebrated for it’s world-class skiing and snowboarding, acclaimed cuisine and one-of-a-kind atmosphere. The four local “super quartet” of mountains: Aspen, Snowmass, Aspen Highlands and Buttermilk will make...
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    Aspen, Colorado 81611
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Free Weds thru Dec 15! Aspen 4/4.5 home 4 night min1 / 23
    (3)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Reviewed 26 October 2017
    Love this Home! We attended a cocktail party in September and will definitely be booking to stay here when we come back. Huge Luxurious home with everything you need and lots of...
    Reviewed 26 October 2017
    My family comes to Aspen every Fall to enjoy the leaves. It was our first time to rent this home and we really enjoyed it! Location was great easy walk to town!! We did use the...
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    About this property
    Beautiful home in Aspen, 12 minute walk from the gondola! Bus service at end of the street, quiet neighborhood with park behind it. Park has playground, picnic area, fountain and a pond, and trails! This home is located on Robinson Road, which is off Alpine, one street past the Smuggler turn....
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    Aspen, Colorado 81611
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    Cloud Nine at Aspen Highlands is equipped with an elevator accessing the four bedrooms, a spacious kitchen, an entertaining area with a stone fireplace, and more. The alpine-style aesthetic flows throughout the home, incorporating stone, wood, and mountain lodge architecture. Ski Accessible:...
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    Aspen, Colorado 81611
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hyatt Grand in Aspen, Colorado is well known for its stunning beauty and legendary charm and is the perfect setting for your vacation. Beautiful residence to be your home while on your vacation. Sleep in these luxurious beds with down filled comforters on top of you while you look out your window...
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    Aspen, Colorado 81611
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Silver Kingdom1 / 43
    (5)Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    This spacious 5,000 square foot, 7 bedroom, 6 bathroom deluxe-rated two-story home can sleep up to 18 people. It's located near the Aspen Golf Course just off Cemetery Lane in Aspen's West End. This house provides incredible views of Pyramid Peak, Aspen Highlands, and the Buttermilk/Tiehack ski...
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    Aspen, Colorado 81611
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 18
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • Mountain Views
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***IMPORTANT**** Starting the summer of April 2019 this property will only be sold as a 3 bedroom until further notice. Experience all the best of Aspen, Colorado at this wonderful retreat. Set on 8 acres with a trout pond, private hot tub, large lawn with fire pit, multiple cabins, and located...
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    Aspen, Colorado 81611
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Aspen Colorado Jewel1 / 21
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Reviewed 30 June 2015
    You really can't find a better combination of location and value in Aspen. The bedrooms are first-rate (quality mattresses; flat screen TV's; vaulted ceilings, plenty of...
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    About this property
    Beautiful two story home in Aspen. Located in the most prestigious neighborhood called the West End. Beautiful tree-lined street. Very close to the music tent. Only 1 1/2 blocks to the nearest bus stop. If you know Aspen, you know that everyone takes the buses. They are great! My home is...
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    Aspen, Colorado 81611
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    • Hot Tub
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ritz Carlton Club defines luxury ski condos in the Colorado mountains and among Aspen ski resorts.  This Ritz vacation rental provides the ultimate Colorado ski vacation experience among all Colorado ski destinations.  These Ritz Carlton Aspen Highlands luxury condos are exquisitely furnished,...
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ritz Carlton Club defines luxury ski condos in the Colorado mountains and among Aspen ski resorts.  This Ritz vacation rental provides the ultimate Colorado ski vacation experience among all Colorado ski destinations.  These Ritz Carlton Aspen Highlands luxury condos are exquisitely furnished,...
    View all property information
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Hot Tub
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ritz Carlton Club defines luxury ski condos in the Colorado mountains and among Aspen ski resorts.  This Ritz vacation rental provides the ultimate Colorado ski vacation experience among all Colorado ski destinations.  These Ritz Carlton Aspen Highlands luxury condos are exquisitely furnished,...
    View all property information
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ritz Carlton Club defines luxury ski condos in the Colorado mountains and among Aspen ski resorts.  This Ritz vacation rental provides the ultimate Colorado ski vacation experience among all Colorado ski destinations.  These Ritz Carlton Aspen Highlands luxury condos are exquisitely furnished,...
    View all property information
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • DVD Player
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ritz Carlton Club defines luxury ski condos in the Colorado mountains and among Aspen ski resorts.  This Ritz vacation rental provides the ultimate Colorado ski vacation experience among all Colorado ski destinations.  These Ritz Carlton Aspen Highlands luxury condos are exquisitely furnished,...
    View all property information
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Air Conditioning
    • Washer
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ritz Carlton Club defines luxury ski condos in the Colorado mountains and among Aspen ski resorts.  This Ritz vacation rental provides the ultimate Colorado ski vacation experience among all Colorado ski destinations.  These Ritz Carlton Aspen Highlands luxury condos are exquisitely furnished,...
    View all property information
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    • Balcony
    • Hot Tub
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ritz Carlton Club defines luxury ski condos in the Colorado mountains and among Aspen ski resorts.  This Ritz vacation rental provides the ultimate Colorado ski vacation experience among all Colorado ski destinations.  These Ritz Carlton Aspen Highlands luxury condos are exquisitely furnished,...
    View all property information
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Air Conditioning
    • Internet Access
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ritz Carlton Club defines luxury ski condos in the Colorado mountains and among Aspen ski resorts.  This Ritz vacation rental provides the ultimate Colorado ski vacation experience among all Colorado ski destinations.  These Ritz Carlton Aspen Highlands luxury condos are exquisitely furnished,...
    View all property information
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Balcony
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ritz Carlton Club defines luxury ski condos in the Colorado mountains and among Aspen ski resorts.  This Ritz vacation rental provides the ultimate Colorado ski vacation experience among all Colorado ski destinations.  These Ritz Carlton Aspen Highlands luxury condos are exquisitely furnished,...
    View all property information
    Location Information
    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Balcony
    • DVD Player
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ritz Carlton Club defines luxury ski condos in the Colorado mountains and among Aspen ski resorts.  This Ritz vacation rental provides the ultimate Colorado ski vacation experience among all Colorado ski destinations.  These Ritz Carlton Aspen Highlands luxury condos are exquisitely furnished,...
    View all property information
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Ritz Carlton Club defines luxury ski condos in the Colorado mountains and among Aspen ski resorts.  This Ritz vacation rental provides the ultimate Colorado ski vacation experience among all Colorado ski destinations.  These Ritz Carlton Aspen Highlands luxury condos are exquisitely furnished,...
    View all property information
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    Aspen, Colorado 81611
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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