The OG Women of Vacation Rentals: Honoring the Trailblazers that Shaped the Future of the Industry

In an industry that’s evolved rapidly in the last few decades, it’s easy to forget that vacation rentals weren’t always a tech-powered, data-driven business. Before booking engines, dynamic pricing tools, and automated check-ins, the vacation rental world was built on spiral notebooks, whiteboards, and—most importantly—people with vision.

In our latest episode, we had the absolute privilege of sitting down with three of those visionaries: Jeanne Dailey (Newman-Dailey Resort Properties), Valerie Hawkins (Perdido Key Realty), and Audrey Miller (Cottage Connection of Maine).

These women aren’t just successful business owners, they’re pioneers who helped lay the foundation for the short-term rental industry as we know it today.

Starting From Scratch—Literally

One of the most striking themes of the conversation is just how hands-on and scrappy the early days were. Reservations were tracked with handwritten charts and masking tape. Marketing involved color flyers, local connections, and mimeograph machines. Cell phones were bulky, the internet didn’t exist, and industry-wide technology was decades away.

Each of our guests built their businesses from the ground up with little more than intuition, creativity, and a deep love for hospitality.

Leading in a Male-Dominated Space

Another powerful takeaway: these women were carving out space in an industry and era where leadership was almost exclusively male. Rather than shy away from the challenge, they leaned into it.

Whether it was keeping a partner's name in the company to be taken seriously or making bold decisions that redefined guest experience, their stories show us what resilience and quiet confidence can build.

Innovators, Even Before Innovation Was a Buzzword

Long before “tech stack” was part of the vocabulary, these leaders were pushing boundaries. They were among the first in their markets to build websites, offer online booking, adopt property management software, and develop operational systems that could scale.

Even when the tools didn’t exist—they created them.

Advocacy with Purpose

We also dove into a topic that’s increasingly critical in our industry: advocacy. Each of these women has fought hard to protect the integrity of short-term rentals in their communities, whether on the Florida Panhandle or the coast of Maine. Their leadership reminds us that being part of this industry means taking responsibility for its future.

A Legacy of Impact

Perhaps the most moving part of this episode is hearing how each woman defines success not in units or revenue, but in relationships. Guests who became friends. Employees who became leaders. Communities are made stronger because of their presence.

Watch the full episode here: