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Ashley Regan

Head of Global Marketing

After earning her degree in International Business and Spanish from the College of Charleston in 2015, Ashley built a successful corporate marketing career while traveling the world. She later transitioned into the vacation rental industry, serving as Head of Global Marketing for one of the largest U.S. property management companies before launching her own portfolio of rentals in domestic and international markets. With deep industry expertise, she’s passionate about creating memorable guest experiences through trusted, standout brands. Outside of work, Ashley enjoys hiking, skiing, spending time on the water, and being with her family and bernedoodle, Kala. Her local favorites include Xao Biscuit, Felix, Chubby Fish, and Chico Feos.