10 Must-See Family-Friendly Aspen Vacation Rentals

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.