Aspen

2026 Short Term Rental Market Outlook

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What the latest market data, regulation changes, and travel forecasts mean for the people who own vacation homes in 2026. The short-term rental industry spent most of the last five years swinging from one extreme to the other. After the pandemic-era boom, the post-boom correction, and a stretch where supply was growing faster than demand … Read more

Your Guide to the 2026 Food & Wine Classic in Aspen

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June 19–21, 2026 Every summer, Aspen transforms into one of the most exciting culinary destinations in the country during the annual Food & Wine Classic in Aspen. From June 19–21, 2026, chefs, sommeliers, restaurateurs, winemakers, and food lovers from around the world will gather in Aspen for three days of tastings, cooking demonstrations, wine seminars, … Read more

Understanding Vacation Rental Management Fees and Costs

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When it comes to hiring a short term rental management company, one of the first questions homeowners have is “how much will this cost”? It’s a fair question. Property management fees can look very different from one company to the next, and the industry has not exactly earned a reputation for straight answers. Some companies … Read more

From One Property to Over 1,600 Homes Nationwide

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SkyRun Looks Back on 22 Years of Disciplined, ‘Brick by Brick’ Growth, as the All-American Company Plans and Prepares for Continued Expansion In 2024, SkyRun Vacation Rentals celebrated 20 years in the vacation rental management industry. For the previous two decades, the company remained dedicated to a disciplined, brick by brick, approach to organic growth. … Read more

Understanding Short Term Rental Ownership: What to Know Before Buying a Vacation Rental Property

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Buying a vacation rental property is often seen as the first step to building a real estate portfolio that generates passive income for years to come. With vacation rental usage and ownership surging over the last several years, vacation home ownership is becoming one of the most popular avenues for real estate investing. This guide … Read more

Elevating the Guest Experience: Our Trusted Local Partnerships

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At SkyRun Aspen, delivering an exceptional guest experience goes far beyond providing beautiful homes—it’s about seamless service, thoughtful details, and trusted local expertise. That’s why we’re proud to partner with Wild Path Transport and Lykke & Ro Concierge, two premier Aspen-based businesses. These partnerships allow us to offer our guests a truly integrated, white-glove experience from arrival to … Read more

Your Complete Guide to Aspen Mountain Resort: The Ultimate Holiday Escape

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If you’re dreaming of a winter getaway that feels straight out of a snow globe, Aspen Mountain Resort is where holiday magic becomes real. With world-class skiing, festive events, luxury dining, and a downtown that glows all season, Aspen is the kind of place you visit once and immediately start planning your next trip back. … Read more

SkyRun Aspen Hits the National Stage on The Price Is Right

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Imagine flipping on The Price Is Right and—surprise!—one of SkyRun Aspen’s gorgeous vacation rentals is front and center as the ultimate dream getaway. That’s exactly what happened this past fall when our Aspen property was featured in the legendary Showcase Showdown. For decades, The Price Is Right has been delighting audiences with exciting prizes, and … Read more

SkyRun Named Among Top New & Emerging Franchises

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SkyRun is proud to announce we’ve once again been named one of Entrepreneur magazine’s Top New & Emerging Franchises for 2025. Only 150 franchisors earn this distinction each year, and we’re honored to be named among the other successful franchisors who have also earned a spot on this year’s list. As shared by the Entrepreneur team, companies named to … Read more

aspen things to do

Head to Aspen This Summer for a Jam Packed Summer of Events

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Aspen Food & Wine Classic: A Culinary ExtravaganzaAspen Food & Wine Classic is the premier culinary event of the year, bringing together world-renowned chefs, winemakers, and food enthusiasts. Taking place from June 20-22, this three-day festival is a feast for the senses, featuring cooking demonstrations, wine tastings, and exclusive dining experiences that celebrate the best … Read more

Short-Term vs. Long-Term Rentals

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Which is the Best Option for Your Second Home? If you own a second home, chances are you’ve considered renting it as a way to earn extra income. But with that thought comes a lot of questions – first and foremost is whether to rent it on a short-term basis or on a long-term basis. … Read more

The Top U.S. Vacation Spots in 2025

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The Best Destinations to Visit in Every Season of 2025 As we settle into 2025, it’s the perfect time to set your sights on new vacation adventures and dream-worthy destinations. No matter what type of vacation you’re craving – a warm beach escape or a tranquil mountain hideaway – the U.S. has a destination to … Read more