Building a Brand with Large Group Short-Term Rentals on the Kentucky Bourbon Trail, with Andrew Llewellyn

How do you scale short-term rentals into a hospitality brand for large groups—and use bourbon tourism to keep your calendar full?

In this episode, Brian Hamrick talks with Andrew Llewellyn, founder of Super Stays, about how he's turning old office buildings into boutique-style short-term rentals that host bachelor parties, weddings, and corporate retreats of 8 to 42 people along the Kentucky Bourbon Trail.

Andrew shares:

• Why large group stays outperform traditional Airbnbs

• How to brand and differentiate your STR business from the competition

• The power of upsells: private chefs, curated bourbon tastings, and luxury vans

• How bourbon tourism fuels consistent demand and high occupancy

• Lessons from scaling his first 15-bedroom property and building his next one

• The role of AI automations in streamlining guest communication

If you're exploring short-term rental investing, hospitality branding, or large group travel, this episode is packed with practical strategies and inspiration.

Find out more:

https://superstaysstr.com/

https://andrewllewellyn.com/

Instagram & Linkedin: @IamAndrewllewellyn

Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area.

https://www.livegreenlocal.com

And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and medicare benefits.

https://www.rcbassociatesllc.com