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SkyRun's Mission Statement

We find new and better ways to let second home owners get the most out of their properties and let guests get the most out of their vacation experiences.


Our Story

In 2004, Barry Cox and Steve Falk created SkyRun Vacation Rentals, a single location property management company in Keystone, Colorado. Barry had a tech and business consulting background, whereas Steve's background was in legal and market development. They both shared a vision and values while offering complementary skills to one another. As they would later discover, this was a recipe for success.

Before they knew it, it was 2007, the company was growing and the industry was booming. This was an era Barry likes to refer to as the ‘powder days.’ In the mountains, powder days are the days when you get a foot plus of light fluffy new snow, when the fun and ease of being on the mountain is magnified one-hundred times and everyone calls in sick to work.

Throughout that era, Barry and Steve acquired knowledge from three years of professional property management and networking with their peers at conferences and decided that SkyRun's future belonged to multi-location property managers. So, Barry and Steve decided to license their brand, process and systems and enable local entrepreneurs to serve vacation guests and property owners the way the industry has for decades. Locally. As Robert Frost would say, Barry and Steve's decision “has made all the difference.”

Currently, SkyRun is a rapidly growing multi-location organization with six-hundred properties in twenty-five locations. We have created the sweet spot in vacation rental management by combining the advantages of local ownership and management with the efficiencies, power and support of a national brand. We also never forget that guests don’t just want to stay like a local, they want to play like a local and SkyRun ensures that happens.


Our Promise to Owners

Respect. We are stewards of our property owners’ precious homes. We embrace the unique concerns and aspirations each owner has for their home.

Integrity. We do what we say we are going to do. We communicate honestly even when the conversations are difficult.

Friendliness. We are grateful for the communities in which we operate. Our clients and partners are our neighbors and friends. We treat them as such.


Our Promise to Guests

Value. Before, during and after your vacation, you’ll feel that every penny of your money was well-spent and the perks were icing on the cake.

Local touch. With the advice of your vacation host, you’ll experience your destination in ways that you would otherwise never have known.

Fun. Your vacation will be a time of relaxation, entertainment, discovery and escape.

Featured SkyRun Properties

104 Willows Way

Bring the family and enjoy this Downtown Winter Park townhome with plenty of space and one of the hottest locations available. Downtown Winter Park is the ultimate family getaway with access ...

104 Willows Way

Colorado, Winter Park, Winter Park Town
3BR/3.5BA | Townhome | Shuttle Bus | Sleeps 7
Starting at
per Night
2130 The Pines

Huge two bedroom with panoramic views of the golf course and 10 mile mountain range of snow capped peaks. New HDTV's! Sleeps as many as 11.

2130 The Pines

Keystone, West Keystone, The Pines
2BR/2.5BA | Condo | Shuttle Bus | Sleeps 11
Starting at
per Night
1633 Quicksilver

-- Hiking trails are located right outside your door -- Access to the Quicksilver pool and hot tub -- Private grill -- Great for families

1633 Quicksilver

Keystone, West Keystone, Quicksilver
2BR/2BA | Condo | Shuttle Bus | Sleeps 6
Starting at
per Night