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2026 SkyRun Annual Conference

SkyRun Locations Gathered in Puerto Rico to Share Ideas and Celebrate Successes

This year, we took our annual SkyRun conference to a sunny island locale. SkyRun franchisees and their key employees gathered in San Juan, Puerto Rico with other industry leaders from across the short-term rental space to discuss new ideas, strategies, and tools to help them succeed in the industry.

While sharing ideas and tips was a main focus of the event, it was also a time for us to celebrate all the wins we’ve had over the past year. We ended the week with an awards dinner to congratulate our locations on all the hard work they put in to grow their businesses. Read on to see which of our locations took home top honors this year.

Fastest Growing Locations

Locations with the highest revenue growth over the previous year

New Category – Less than 2 Years in Operation
SkyRun Galveston

Beth Harp, Owner

Emerging Category – 2 to 4 Years in Operation
SkyRun Denver

Sebastien Guite, Owner

Established Category – More than 5 Years in Operation
SkyRun North Lake Tahoe

Steve Schmidt, Owner

Guest Satisfaction Excellence

Awarded based on guest review scores

New Location

New Category – Less than 2 Years in Operation
SkyRun Twin Cities

Craig & Theresa Schaefer, Owners

Emerging Locations

Emerging Category – 2 to 4 Years in Operation
SkyRun Big Bear

Phil & Serena Chap, Owners

Emerging Category – 2 to 4 Years in Operation
SkyRun Grand Junction

Wayne & Wanda Cooley, Owners

Emerging Category – 2 to 4 Years in Operation
SkyRun Kona Coast

Rich & Toni White, Owners

Emerging Category – 2 to 4 Years in Operation
SkyRun North Naples

Kimberly Layton, Owner

Established Locations

Established Category – More than 5 Years in Operation
SkyRun North Lake Tahoe

Steve Schmidt, Owner

Established Category – More than 5 Years in Operation
SkyRun Park City

Michael LeClerc, Owner

Established Category – More than 5 Years in Operation
SkyRun Phoenix

Peter & Maria Vlahos, Owners

Established Category – More than 5 Years in Operation
SkyRun Rocky Mountain National Park

Larry Whitty, Steve Falk, & Lukas Krause, Owners
Connor Dolan, General Manager

Best New Location

Awarded to the new location that has established the strongest foundation for growth.

SkyRun Whitefish

Whitney Elenbaas, Owner

Most Innovative Location

Awarded to the location that has improved guest and owner experience through new ideas and processes that can be used across the SkyRun brand

SkyRun Kiawah

Matt Demirjian & Michael LeClerc, Owners

SkyRun Best of Brand

Each year at our annual conference, we also award the best of the best in the SkyRun family with our Best of Brand contest. Our Best of Brand program is a friendly competition among our locations awarding those who go above and beyond to grow their portfolio, engage with SkyRun initiatives, and deliver superior service. Check out who took home top prizes in this contest in our dedicated Best of Brand blog post.

Special Thanks to Our Sponsors

Our annual conference could not take place without the support of our wonderful sponsors from across the vacation rental industry. We want to thank them for taking time out of their busy schedules to join us in Puerto Rico to connect and discuss this industry we all love so much. Working together is the best way to find new solutions and continue delivering unforgettable experiences for guests. Thanks to Booking.com, Besty AI, Dimaco Direct Mail Company, Dry Fly Digital, Homes & Villas by Marriott Bonvoy, HostGPO, Minoan, Rental Guardian, Sojo, Track, Virturance, and Vrbo.