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aspen vacation rentals

Book your Aspen Vacation Today!


Aspen. “Where the beer flows like wine and the women instinctively flock like the salmon of the Capistrano.” It’s true. But it’s so much more. Aspen is the world’s smallest big city. All the warmth and charm of a small town, with all the arts, culture, food and drink, and nightlife of a major metropolis.

This is a real community, grounded in history, and set at the foot of the most beautiful mountains in Colorado. We love our visitors, and can’t wait to show you around. Let us introduce you to the magic we found and fell in love with and has kept us here for all these years.

Call to meet our man on the ground, Skippy Mesirow, our Aspen lead and learn about how your stay in the Roaring Fork Valley might just change your life.

Enter your vacation dates and search our rentals above or call 1.970.236.2444

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Aspen/Snowmass
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Aspen/Snowmass Vacation Rental Properties
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SkyRun is currently seeking new vacation properties for this site!
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Featured Aspen Properties

- No Fancy-Pants Frills, All the Essentials- Staggering Views of the Whole Valley- Sleeps 14+ for Unmatched Value- Special Rates and Option for Non-Profits & Community Serving Organizations

711 Spruce St. 6BR
711 Spruce St. 6BR
711 Spruce St. 6BR
711 Spruce St. 6BR
711 Spruce St. 6BR

711 Spruce St. 6BR

Town of Aspen
6BR | 5.5BA | Sleeps 18 | Mountain/Shuttle Bus
Starting at
$700.00
per Night

- Exquisite Contemporary Design and Detailing- Ski-In-Ski-Out Accessibility- Fully Appointed Luxury Experience

Aspenwood L6
Aspenwood L6
Aspenwood L6
Aspenwood L6
Aspenwood L6

Aspenwood L6

Snowmass Village
1BR | 1BA | Sleeps 4 | Mountain
Starting at
$200.00
per Night

- Charming, warm chalet Style studio- Located On Aspen Mountain- Ski-in Ski-out with a hot tub! Cozy up to the mountain in this Euro-chique chalet style studio. Ideally located to explore all four season in Aspen, Colorado. Found at the base of Aspen Mountain (Ajax) this quaint spot is an ideal jump-off for a ski vacation, seconds from mountain trails for fall leaf peeping, and right in the heart of Aspen for all fantastic summer and spring events, retreats, festivals, and more! Please...No ...

305A Fifth Avenue Condos
305A Fifth Avenue Condos
305A Fifth Avenue Condos
305A Fifth Avenue Condos
305A Fifth Avenue Condos

305A Fifth Avenue Condos

Town of Aspen
1BR | 1BA | Sleeps 2 | Shuttle Bus/Ski-In
Starting at
$175.00
per Night

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