• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer

TravelAwaits

Our mission is to serve the 50+ traveler who's ready to cross a few items off their bucket list.

  • Destinations
    • United States
    • Europe
    • Asia
    • Canada
    • Mexico and Caribbean
    • Central and South America
    • Australia and South Pacific
    • Africa
    • Middle East
    • Antarctica and Arctic
    • See All
  • Activities & Interests
    • History and Culture
    • Outdoor Activities
    • Food and Drink
    • Sightseeing
    • Seasonal Travel
    • National Parks
    • State Parks
    • Hotels and Resorts
    • Wildlife
    • Beaches
    • Shopping
    • Festivals and Special Events
    • Theme Parks
    • Photography
    • Reading
    • See All
  • Types of Travel
    • Cruises and Sailing
    • Road Trips
    • Group Travel
    • RVing
    • Camping
    • Rail
    • Wellness Travel
    • Adventure Travel
    • Ancestry Travel
    • Naturism
    • LGBTQ+ Travel
    • Budget Travel
    • Weekend Getaway
    • Bucket List Trips
    • Family Vacations
    • Solo Travel
    • Full-Time Travel
    • Pet-Friendly Travel
    • See All
  • News & Tips
    • Travel News
    • Travel Tips
    • Travel Products
    • Travel With Confidence
    • Gift Guides
    • See All
  • Inspire
  • Retire
  • Best Of Travel Awards
  • Destinations
  • United States
  • Colorado
  • Aspen
  • Activities and Interests
  • Hotels and Resorts
  • Vacation Rentals
  • Types of Travel
  • Family Vacations
  • DestinationsUnited StatesColoradoAspen

    10 Must-See Family-Friendly Aspen Vacation Rentals

    William Stupp
    October 02, 2022

    Aspen is practically a byword for a luxury vacation destination. It attracts skiers, naturally, but also those who simply love the scene. What a scene it is! The town abounds with shops, galleries, and one-of-a-kind restaurants. Everyone ought to take a day trip to this Rocky Mountain gem, but it’s far better to uproot the family and stay as long as you can.

    Videos by TravelAwaits

    Perhaps you are drawn by the thrills of winter sports. Skiing is the top one, but other wintertime activities include dogsledding and seeing the Christmas sights. Aspen’s glory, however, is evergreen, extending long after the snows melt. There’s hiking, a regular stream of festivals, and much more. Fall is a time of incredible bargains and colorful displays put on by the trees after which the town is named.

    Mountain life is about more than just skiing. There is shopping, nightlife, fine dining, and family fun. The world has many mountains, but there’s only one Aspen. It stands out above the rest.

    Famously luxurious, Aspen is home to many incredible homes. Below you’ll find a section of 10 of the finest. Each is ideal for a family vacation. They have room for everyone and provide access to Aspen’s delights, those found on the mountain as well as those in town.

    Do note that prices fluctuate significantly throughout the year and the rates listed below reflect a year-round average.

    Four Peaks Estate

    It speaks to the brilliance of this property’s architects that every inch of the more than 13,000 square foot home looks impeccable. It sits on three majestic acres outside town, a short drive from all three skiable mountains. The location is stunning and the designers of this haven have truly done it justice, as the photographs will show. Each of the five bedrooms might be considered a “master” at a lesser home and is perfect for a large family getaway. From the windowed dining room to the leathered-up living room and home theater, there is something stunning behind every door.

    Dreaming of Aspen – your dream vacation awaits you
    4 reviews
    Private vacation home
    10 Guests
    5 Bedrooms
    7 Bathrooms
    Top guest reviews
    Hello Blair, The Cuvee Starwood home was Fabulous and exceeded our expectations. The views are to die for and the accommodations the absolute best. The furnishings, linens, floorplan, were perfect, impeccable, fully stocked and tastefully decorated. We celebrated my husbands 60th Birthday and had a wonderful hands-on cooking experience with chef “Susie Jimenez” who made the night one of the most memorable evenings ever. The menu was over the top amazing and she was delightful! I would highly recommend her to anyone. The staff, Blair, Kait, management Ben, were extremely helpful, personable and accommodating. I would highly recommend this 5star resort home to anyone going to Aspen, a truly wonderful vacation. Thank you, Barbara”
    Hello Blair, The Cuvee Starwood home was Fabulous and exceeded our expectations. The views are to die for and the accommodations the absolute best. The furnishings, linens, floorplan, were perfect, impeccable, fully stocked and tastefully decorated. We celebrated my husbands 60th Birthday and had a wonderful hands-on cooking experience with chef Susie Jimenez who made the night one of the most memorable evenings ever. The menu was over the top amazing and she was delightful! I would highly recommend her to anyone. The staff, Blair, Kait, management Ben, were extremely helpful, personable and accommodating. I would highly recommend this 5star resort home to anyone going to Aspen, a truly wonderful vacation. Thank you, Barbara
    Everything about our experience with Four Peaks was incredible. Rita and Crystal did an amazing job taking care of our every need. If we needed anything, these two ladies took care of it immediately. The house was a dream. Stunning views and spacious rooms! We will return to this house in the near future!
    Everything about our experience with Four Peaks was incredible. Rita and Crystal did an amazing job taking care of our every need. If we needed anything, these two ladies took care of it immediately. The house was a dream. Stunning views and spacious rooms! We will return to this house in the near future!
    The property was gorgeous! I loved all the big windows throughout the house to see the beautiful mountain views. From the attention to detail, fresh appetizers upon arrival, and pre-trip planning, Cuvée made everything seamless and I can’t wait to visit Aspen again soon!
    Read Less ∧
    Read More ∨
    View Deal

    Aspen Ski Den

    Aspen has a lot to offer, from skiing to shopping to luxury homes. This large single-family home is a superb example of the latter, a property that allows guests to take in the former diversions with ease. Within walking distance of the heart of Aspen, it is in the perfect location with something to please everyone. Five splendid bedrooms have unique charms but share the principle that light ought to be let in. From charming brick walls to wood paneling, the home will please aesthetes with its non-ostentatious take on luxury living.

    Dreaming of Aspen – your dream vacation awaits you
    0 review
    Private vacation home
    10 Guests
    5 Bedrooms
    4 Bathrooms
    View Deal

    Victorian Home On The Eastern Edge

    From the tranquil blue exterior to the restored 1930s bathroom, this Victorian home is a fine place for a mountain family. It is about a 10-minute walk from the slopes and shops that made Aspen famous. During that stroll, you’ll see few houses as charming as this one. The large backyard is naturally equipped with a hot tub and garden. Thoroughly modernized, the home retains quaint elements of how mountain life used to be, such as a wood-burning stove. Though rendered obsolete by the home’s radiant heating, it still provides a (less literal) sense of warmth.

    Dreaming of Aspen – your dream vacation awaits you
    38 reviews
    Private vacation home
    10 Guests
    5 Bedrooms
    5 Bathrooms
    View Deal

    Red Mountain Masterpiece

    Taking careful note of the surroundings, architect Chad Oppenheim has created a home worthy of Aspen’s natural beauty. A unique building for a unique family, it is the cause of many jaws dropping and a perennial source of memory making. It makes bold use of the area’s natural materials and the gambit certainly pays off. The outdoor areas are as thoughtfully crafted as those inside. Large boulders, set down after millennia by receding glaciers, look suspiciously as though they have been placed intentionally. This getaway has four bedrooms and offers innumerable opportunities to experience awe.

    Dreaming of – your dream vacation awaits you
    0 review
    10 Guests
    4 Bedrooms
    5 Bathrooms
    Oops, this listing is currently inactive. Check out these alternative properties in the same location!
    View Deal

    Sprawling West Aspen Home

    Aspen’s three mountains can accommodate a great many skiers. Likewise, this envy-inducing vacation home can host a large troupe of guests (18 to be precise). It’s in a great location in West Aspen, near the golf course and a shuttle stop that can carry the whole group to town and mountains alike. The home features plush carpets, posh furniture, and seven bedrooms in various configurations. Common areas abound, indoors and out. Guests would be remiss not to check out the backyard trail to Red Butte once the snows melt.

    Dreaming of Aspen – your dream vacation awaits you
    19 reviews
    Private vacation home
    18 Guests
    7 Bedrooms
    6 Bathrooms
    Top guest reviews
    We needed a rather large place for a family reunion. With 7 BRs and 6 Baths this was a perfect fit. Great location in Aspen-about 2 miles to the airport and the same to downtown. The public free bus line stopped at our street giving easy access to everywhere. We highly recommend this home
    Great time bus stop one house down the street
    Large home with double kitchen and living rooms. We were only eight people and it was super spacious. Great home for a large group. Excellent views and we enjoyed the hot tub. Well equipped. Nice location on bus line.
    Excellent
    Very well appointed. Kitchens were both equipped well. perfect for a bubble group to enjoy each other and enjoy skiing aspen
    Read Less ∧
    Read More ∨
    View Deal

    Mountain Laurel Springs

    Enjoy a profound sense of freedom as you take in commanding views of Independence Past from this amazing Aspen home. Skiers and shoppers alike will appreciate the home’s proximity to the bus. The living room is truly grand, and not only because of its mountain views — the furnishings are also easy to admire. No one will feel left out as each bedroom is something to write home about, even the downstairs kids’ room with a pair of twins.

    Dreaming of Aspen – your dream vacation awaits you
    0 review
    Private vacation home
    8 Guests
    4 Bedrooms
    3 Bathrooms
    View Deal

    The Observatory

    Like many mountain towns, Aspen is a great locale for stargazing. The best place to see the universe’s best and brightest is this landmark home in central Aspen. Built in the late 1880s, the house doubles as an observatory. The telescope has been upgraded, but the structure remains the same, as charming as ever. Not only a work of art in and of itself, but the Observatory also boasts a fine collection. There’s room for 12 overnight guests and seating for even more should you make use of the splendid kitchen to throw a dinner party. The whole family will take delight in exploring every corner of this unique vacation home.

    Dreaming of Aspen – your dream vacation awaits you
    3 reviews
    Private vacation home
    12 Guests
    6 Bedrooms
    7 Bathrooms
    Top guest reviews
    The Cuvee team was wonderful host and the house was perfectly located in downtown Aspen. Great launching pad for ski adventure with friends.
    This was my second time staying at this property. The location is convenient for skiing access on Aspen Mtn, transportation at Ruby Park, and the whole downtown area. The property manager was exceptionally responsive to any issues that arose. Would definitely stay again.
    Read Less ∧
    Read More ∨
    View Deal

    Robinson Road Ski House

    A 12-minute walk to ski paradise, this four-bedroom home is itself quite heavenly. It has four bedrooms. Each has an en suite bathroom and a king-size bed. Two even have fireplaces of their own (residents of the other two will have to settle for the one in the homey living room). Other perks include a rooftop hot tub, a backyard pond, and conveniences like the next-door park and playground. It really is a family home: even the dogs are allowed for a $30-a-night fee. Extra guests will be comfortable on one of three sofa beds.

    Dreaming of Aspen – your dream vacation awaits you
    48 reviews
    Private vacation home
    10 Guests
    4 Bedrooms
    5 Bathrooms
    Top guest reviews
    Great house and facilities. Excellent for our family gathering.Park near house was excellent for children play with just grandpa supervision.House had everything we needed and more.
    The house is perfect families and a great location. Easy walk to town.
    Perfect location for our son’s wedding. There was plenty of areas for us to be together and to get ready for our events. Thanks for sharing your home!
    Large, luxurious bedrooms. Convenient location and helpful hosts.
    Wonderful stay. The house was perfect location in Aspen. Will be back!
    Read Less ∧
    Read More ∨
    View Deal

    Split-Level Condo At Aspen Alps

    Getting the whole family to ski together is always a struggle. That is less true for guests at this incredible Aspen Alps condo. As a ski-in/ski-out accommodation, it’s easy to make sure everyone goes down together at least once. Two well-appointed bedrooms are on the lower level (a king and a room with two doubles). The glorious master suite is above, as is a queen room. The condo has a patio with a grill and gondola views, and a living room furnished with fine leather furniture.

    Dreaming of Aspen – your dream vacation awaits you
    10 reviews
    Condo
    8 Guests
    4 Bedrooms
    3 Bathrooms
    Top guest reviews
    Rating Details:The property manager was very helpful.The vacation rental was spotless.I was very happy with the location.I was very satisfied with the condition of the vacation rental.Overall, I recommend this vacation rental.Reviewer Comments:We arrived for a three day stay to enjoy Aspen, enjoy foliage, see Maroon Bells , hike and take the Silver Queen gondola up Ajax. Condo was actually much nicer than pictures suggested. Excellent location next to the gondola, yet quiet and private. Great outdoor patio , huge living and dining room. A very fitting setting to celebrate my 70 th.
    Really nice place to stay in aspen. Your backyard is the gondola , can’t beat the location. Love having a back patio where you could sit outside and enjoy the Colorado air. The interiors are amazing , everything is clean. Nice we too with two bedrooms up and two down. Enjoyed the location immensely, would just walk down the slope a bit to the base of mountain where we would shop . Coffee, eat!
    What a fantastic place. We loved the property from the ease of getting into town as well out on the mountain. Couldn’t recommend it more highly!
    The unit is nice, however, bathrooms are in need of remodeling.
    Great condo with great location. Within walking distance of downtown. Ski in/ski out. There are a lot of stairs to get to condo but view is beautiful.
    Read Less ∧
    Read More ∨
    View Deal

    Wonderfully Restored Home From 1888

    A remarkable piece of evidence attesting to Aspen’s eternal draw, this home from the late 19th century shows that mountain life is not some passing fancy, but an everlasting obsession. A true family home, this house in central Aspen has character, all thanks to its pedigree and the diligence of its keepers. Many elements of the original design remain, such as bathroom sinks and exposed beams. The new additions (including buffalo leather sofas and faux-Victorian beds) by no means detract from the home’s character.

    Dreaming of Aspen – your dream vacation awaits you
    20 reviews
    Private vacation home
    8 Guests
    4 Bedrooms
    3 Bathrooms
    Top guest reviews
    Everything was perfect highly recommend
    Thank you for sharing your home with us! Property exactly as listed and the host was very friendly and helpful. I hope to have opportunity to return.
    Great location and a cozy and comfortable house with nice back yard.
    What an amazing place – if looking to stay downtown in an charming home with great hosts, look no further.
    Our family had a wonderful stay over the Holidays. Plenty of space and we really enjoyed the ability to walk to everything we wanted to do. Dennis was very easy to reach and got back to us right away with answers to any questions.
    Read Less ∧
    Read More ∨
    View Deal

    If you are looking to discover more in and around Aspen check out:

    • Fantastic Things To Do In Aspen, Colorado During The Winter
    • The Best Things To Do In Aspen Besides Skiing

    Primary Sidebar

    Recommended Articles

    Travel Tips for Nordic & Scandinavian Countries: Culture, Currency, & More
    Sink Your Teeth into These Acclaimed Dallas Steakhouses
    Must-See Alaska Beaches: Black Sands, Wildlife Sightings, & More
    My Top 20 Luggage Picks for Carry-Ons, Check-Ins, & More—Plus, Shopping Tips
    Sign up for our newsletter
    It's our time to explore
    Our mission is to serve the 50+ traveler
    We want to inspire you to explore new destinations, discover new experiences and savor the journey. Our goal, to share the world’s unique, hidden and once in a lifetime locations with you to create unforgettable memories.
    • About Us
    • Contact Us
    • Terms of Use
    • Privacy Policy
    Do Not Sell My Personal Information Change Consent