Aspen Vacation Rentals

Cabins, condos, and single family homes for rent in and around the Aspen area

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Visit Aspen

Some people say Aspen is the world’s smallest big city. Enjoy the warmth and charm of a small town while indulging in the culture, dining, and nightlife of a major metropolis.

Your Aspen Vacation, Your Way.

Ski in/Ski Out

Premium Properties

Pet Friendly

Find Your Aspen Rental

Flexible Cancellation
Premium Property
Premium Property

Sonn 3

Snowmass Village, CO

4 Bdrms 0 Baths 8 Guests
From $626.00
4.9
per night + taxes & fees
View Details
Flexible Cancellation

29C

Snowmass Village, CO

2 Bdrms 2 Baths 6 Guests
From $150.00
4.8
per night + taxes & fees
View Details
Flexible Cancellation

FH4

Aspen, CO

3 Bdrms 0 Baths 7 Guests
From $645.00
5.0
per night + taxes & fees
View Details
Featured Property
Flexible Cancellation

D2

Snowmass Village, CO

3 Bdrms 2 Baths 6 Guests
From $239.00
4.9
per night + taxes & fees
View Details
Featured Property
Flexible Cancellation

921

Snowmass Village, CO

5 Bdrms 7 Baths 14 Guests
From $1,250.00
5.0
per night + taxes & fees
View Details
Flexible Cancellation

E3

Snowmass Village, CO

3 Bdrms 3 Baths 6 Guests
From $322.00
4.0
per night + taxes & fees
View Details
Flexible Cancellation
Premium Property
Premium Property

229 #35

Snowmass Village, CO

3 Bdrms 4 Baths 8 Guests
From $999.00
5.0
per night + taxes & fees
View Details
Flexible Cancellation

LC5

Aspen, CO

3 Bdrms 2 Baths 8 Guests
Pet Friendly
From $522.00
4.9
per night + taxes & fees
View Details
Featured Property
Flexible Cancellation

2E

Aspen, CO

1 Bdrm 0 Baths 4 Guests
From $211.00
4.8
per night + taxes & fees
View Details
Flexible Cancellation

229 #36

Snowmass Village, CO

3 Bdrms 2 Baths 8 Guests
From $564.00
5.0
per night + taxes & fees
View Details
Flexible Cancellation

1068

Snowmass Village, CO

3 Bdrms 3 Baths 7 Guests
From $662.00
5.0
per night + taxes & fees
View Details

Featured Aspen
Vacation Rentals

Your Local Team

Locally Owned and Operated In Aspen

Aspen isn’t just a vacation destination set amongst the most beautiful mountains in Colorado – it’s also a real community that’s grounded in history, yet always looking toward the future.

Remember, when you rent with SkyRun Aspen, you can expect superior, prompt, and personalized service that’s hard to find in a top-down rental corporation.

  • Enjoy a personal relationship with your property manager, who can answer any questions and address all concerns promptly.
  • Have a question about local activities, amenities, or services? Our local staff can provide recommendations for getting the most out of your stay. 
  • Our property managers are just a stone’s throw away from most of our rentals. That means they’re available to step in to help with any situation. 

Skippy Mesirow is the general manager for SkyRun Aspen and a long-time Aspenite. Outside of his work with SkyRun, he’s extremely active in local politics. He loves working with SkyRun guests and is always happy to share the best of what Aspen has to offer.

Skippy Mesirow

Aspen, Colorado

General Manager

Let's Talk!

Aspen Mountain

Although it’s now one of four ski resorts in the area, Aspen Mountain is the one that started it all. When you ski here, you’re skiing history. Tip: If you want to sound like a local, call this peak namesake by its original name: Ajax. Be aware that Aspen Mountain doesn’t have any green circle or beginner runs. Enjoy your choice of dining options at the peak or the base.

Snowmass

Snowmass is bigger than all the other area resorts combined. With trails for every ability level, Snowmass is an excellent pick for families or groups. If you’re not an early riser, hit the slopes right after the “noon groom” to get that first-ski-of-the-day feel later in the day.

Aspen Highlands

A local favorite, Aspen Highlands is known for incredible views and wide-open trails. If you’re up for the ultimate challenge, check out the expert-only terrain of the Highland Bowl. But if that’s not quite your speed, fear not. The Highlands also features mid-mountain beginner and intermediate trails.

Buttermilk

Buttermilk may be best known as the home of the X Games, but believe it or not, it’s also a great place to learn to ski or refine your skills. Take your pick of challenging trails in the main area, build your confidence on the gentle downhills in the beginner’s area, or take your fun in the other direction by tackling Tiehack, the all-day uphill route.

Fine Dining

Whether you’re looking for a casual but delicious bite après-ski or you’re craving a dining experience worthy of a Michelin star, Aspen has you covered. World-class chefs from across the globe have elevated Aspen’s food scene to heights that rival our mountains.

Shopping

From Prada and Gucci to local consignment stores that offer luxury goods for a veritable steal, Aspen is a shoppers’ paradise. Did you know that Ralph Lauren considers Colorado to be one of his muses? Pop into his Aspen store to see what has inspired him lately.

Spas

Aspen is all about pampering yourself. Hoping to indulge in a facial, massage, or med-spa service during your visit? Choose from any number of spa locations at a variety of price points.

Nightlife

See and be seen or hide away in a subterranean speakeasy. Go club hopping or hit the slopes for some night skiing. Take in some live music or try your luck at a billiard’s bar. Aspen’s infamous nightlife scene truly has something for everyone.

Hiking & Biking

Aspen’s location in the Roaring Fork Valley means it’s perfectly situated for hiking and cycling enthusiasts of every level to get out and explore. Be sure to hike through West Maroon Pass to take in stunning views of the Maroon Bells at Maroon Lake.

Fishing

The Aspen area offers an incredible 45 miles of Gold Medal waters. Hire a local guide to get the inside scoop on the best locations and current conditions. Make sure to get a Colorado fishing license before your trip.

Water Sports

Whitewater rafting, paddleboarding, kayaking, swimming … summer in Aspen offers ample opportunity to experience and enjoy the natural scenery while keeping cool.

Arts & Culture

Aspen’s summer music festival attracts world-class performers all summer long. Filmfest, held every fall, features a first look at some of the hottest upcoming feature films.The
Aspen Art Museum features bold contemporary art throughout the year.

Rental Car Discount

Receive preferred pricing on car rentals with Avis or Budget. Car pickups are available at regional airports or at any other Avis/Budget location.

Ski Butlers

SkyRun guests receive 10% OFF with Ski Butlers!
Ski Butlers will come directly to your door with their FREE delivery service. From professional boot fittings to unlimited equipment swap-outs, Ski Butlers has partnered with SkyRun to ensure your stay in Aspen is truly remarkable! Book online or call 877.754.7754.

Childcare

For date night or ski days, Aspen Nannies can provide a safe and fun experience for your children. SkyRun customers receive 10% off. Email contact@aspennannies.com or 970-376-4054 for the top babysitters in the valley.

Concierge Service

To make your stay seamless, we have partnered with KEY, a five-star concierge service. KEY’s team of local experts can handle everything from transportation and pre-arrival grocery delivery to privately guided outdoor adventures and coveted restaurant reservations. Request a personalized itinerary online or call 970.658.5844.

What To Expect

Get that “home away from home” feel while enjoying the streamlined, convenient guest experience that includes full attention to every detail.

During your stay, you can expect SkyRun staff to be close by and available to help you make the most of your trip. You can reach them via web chat, email, text, or phone. They’re available and accessible daily, and on-call 24/7 for emergencies.

What’s included
Independent homeowners contract with SkyRun Vacation Rentals to professionally manage their properties and create stellar vacation experiences for their guests.

Every SkyRun property is unique, so certain features and amenities are variable. To ensure you’re selecting the right property for your needs, review the photos and note the amenities listed for the property. Read the sections called “What you’ll love” and “What to be aware of” at the bottom of each listing, and check out reviews from prior guests.

Included Services:

  • Full cleaning prior to your arrival
  • Pre-arrival inspection
  • Wi-Fi and TVs
  • Most properties have free parking (check each property for possible charges)
  • Luxury linens and towels
  • Fully stocked kitchen
  • Cleaning and trash removal upon departure

Included Amenities and Starter Supplies:

  • Coffee and coffee filters (if applicable)
  • Salt and pepper
  • Soap/shampoo/lotion
  • Toilet paper
  • Paper towels
  • Hair dryer
  • Ironing board
  • Dish soap and dishwasher detergent (if applicable)
  • Laundry detergent (if applicable)
  • Alarm clock
  • Firewood (if applicable)

Additional Services:

  • Crib or toddler bed with sheet: $10/day
  • Pump-up bed with sheets: $10/day
  • Mid-stay cleaning service: Ask your local SkyRun staff for pricing
  • Grocery delivery: Cost of groceries +10% + $20/hr
  • Travel insurance: 7% of your stay

Check-In Instructions

Check-In:

  • Check-in is 4:00 p.m. MST. 
  • A check-in instructions email will be distributed to guests 7 days prior to arrival date containing directions and access information for the property.
  •  In most cases guests will access a property via a lockbox or smart lock using the given access code.
  • Early check-ins can only be confirmed on the day of arrival.

 

Check-Out:

  • Check-out is 10:00 a.m. MST.  
  • Guests must depart the property by the check-out time unless a late checkout has been coordinated and confirmed with the SkyRun office.
  • Late check-outs must be coordinated directly with the SkyRun office no later than 9am on the day of departure; please note that if we have an incoming guest we will not be able to accommodate a late checkout.
  • We ask that guests remove major trash from the unit, return the furniture to its original location, and load and run the dishwasher.

 

Parking:

  • Parking may be limited. The check-in instructions email will contain information regarding parking at your property.
  • Any parking fines assessed to your vehicles during your stay will be billed to you if they are billed to us.  Parking fines can be significant.

Travel Insurance

Nationwide® Travel Insurance protects your vacation investment against unforeseen events like a hurricane, sickness, injury, flight cancellation, job loss and much more.

Group coverage protects everyone in your traveling party for one low price.

Get a quote.

Property Damage Waiver

Enjoy peace-of-mind with our incidental damage protection.

SkyRun includes a property damage protection waiver on each reservation. The damage waiver covers damage to the property up to $1,500 so long as the damage is accidental and reported to SkyRun prior to your departure. It does not cover damage that is willful, the result of negligence, or damaged caused by the misuse of household items. It also doesn’t cover unreported damage. SkyRun doesn’t charge our guests a refundable damage deposit in lieu of the waiver. Unlike a refundable damage deposit, the damage protection waiver is non-refundable.

If during your rental of our property, you damage the real or personal property assigned to that property, SkyRun will cover the cost of repairs or the cost to replace the property up to an amount not to exceed $1,500. Should the cost of the damage exceed $1,500 or does not meet the criteria for a “covered loss”, and the property owner’s insurance policy also does not cover the loss, then you shall be responsible for the full amount of the damage which will be charged to the credit card on file. Coverage is provided to you and all travelling companions that are staying in the home overnight during your stay.

Coverage is not provided for loss due to:

  • Your intentional acts or gross negligence.
  • Any damage that occurs if you are in violation of the terms and conditions (including but not limited to having more than maximum occupancy or having a party).
  • Loss, theft or damage to any personal effects owned by you or brought on the covered stay by you.
  • Loss, theft or damage caused by any person other than you or your traveling companions with whom you share the property reservation unless substantiated by a police report.

Your Duties in the Event of Damage. You must:

  • Take all reasonable, necessary steps to protect the property and prevent further damage to it.
  • Report the loss in writing (email ok) prior to check-out to the SkyRun staff.
  • Provide us documentation such as pictures to substantiate the claim.

Property Management You Can Trust

Owning a vacation rental shouldn’t be stressful. Let SkyRun ease your worries and increase your revenue with our vacation rental management solutions.

Why choose SkyRun? As a locally owned & operated business, our homeowners are not just a number to us, they’re our neighbors. But as a franchise, we have access to tools and tech that help you stay ahead of the game. That’s why thousands of second homeowners trust us with their properties.

Learn More

Over the years, we have had about a half dozen other management companies. Since working with SkyRun, we have had more rentals in two years than the other management companies combined over 10 years. They are great to work with!

KathySnowmass, CO

SkyRun’s staff is top notch, and working with them has been fantastic.

TimSummit County, CO

SkyRun’s staff has always treated my properties as if they were their own, and that’s such a comforting feeling. I’m very happy with the income stream generated through SkyRun’s property management!

KarenWondervu, CO

SkyRun provides the attention of a small local business while delivering the rentals of a large corporate business.

LauraSteamboat Springs, CO

Aspen Blog

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Aspen Frequently Asked Questions

SkyRun provides photos, maps, amenity details and reviews about the property you will be renting. Our staff has first- hand knowledge of each property, so don't hesitate to call us if you have any questions.

Our rentals come fully furnished including TVs, high-speed internet, linens and towels, a microwave, dishes, pots, pans, and other kitchen essentials. We sweat the details and provide supplies like shampoo, conditioner, tissues, paper towels, dishwasher detergent, soaps, trash bags, etc. We provide everything you expect from a fine hotel, and then some. Refer to individual listings to see more amenity information, and please contact us directly if you still have questions.

When you book direct with SkyRun you avoid paying service fees that traditional listing channels, like Airbnb, charge. Our prices are also competitive with rent-from-owner rates, but we offer professional service, optional travel insurance, and immediate on-site assistance should the need arise. In addition, we offer exclusive discounts from local businesses, available only to SkyRun guests. SkyRun can help you plan and save on your entire vacation experience, not only the rental itself. We also offer last-minute booking specials.

Travel insurance is an optional addition to your total rental charges. It is offered on our reservation form at the time of booking. It is also usually offered at the time of booking when you booked with a 3rd party booking site. You can also add travel insurance onto your reservation within 48 hours of booking. The cost of travel insurance varies and is usually between 7% - 9.5% of your total reservation cost depending on the coverage type. If you do not have travel insurance, you can not cancel your reservation for any reason. If you have travel insurance and need to cancel or make a claim refer to your specific policy. More information about the travel insurance policies SkyRun offers can be found here.

You can rent any of our properties by booking directly on this website using a credit card or you can call to book a reservation if you would like to speak with a vacation planner. When you book, 1/3 of your total reservation cost or a minimum of $300 is charged as a non-refundable deposit to secure your rental. 30 days before your arrival, the remaining amount is due and becomes non-refundable if you need to cancel for any reason (see travel insurance above for exceptions). At this time, the credit card we have on file will be automatically charged for the balance.

For most properties, SkyRun utilizes a convenient keypad lock system which allows you to enter your vacation rental using a personalized access code, as opposed to having to pick up a key and worrying about keeping track of it during your stay and returning it afterwards. This also saves you the trouble of coming to a check-in center beforehand. Your welcome packet will be in your rental upon arrival, and our staff is always only a phone call away if questions arise.

No smoking and no pets (unless specifically designated as pet-friendly) are allowed in the rentals. No parties where more than the number of people the property sleeps are allowed in the rental at any time. As in your own home, renters are of course subject to citations for noise violations, etc, handed down by public officials. Remember you are staying as a guest in someone's home, where much investment has been made to make your stay enjoyable; please treat all private property with the respect it deserves.

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