Multiply Yourself with AI: Building a Smarter Short-Term Rental Business with Ana Shapiro

What if AI could help you grow your short-term rental business without removing the very thing that makes hospitality feel human?

In this episode of the STR Sisterhood, I’m joined by Ana Shapiro, a real estate investor with nearly two decades of experience and the founder of Chillin Away, a collection of family-friendly short-term rentals designed around connection, comfort, and creating memorable experiences.

After years of managing the moving pieces that come with short-term rentals, Ana realized something important: the biggest limitation in her business wasn’t the properties, the capital, or even demand.

It was that everything depended on her brain.

That realization changed the way she thought about AI. Instead of using it simply as another tool—or trying to automate herself out of the business—Ana began building specialized AI agents to support different functions like revenue management, operations, guest experience, marketing, and financial intelligence.

In this episode, we talk about:

Why short-term rentals are anything but passive when you’re the one operating themHow Ana uses AI to multiply herself rather than replace herselfTurning the knowledge in your head into systems that can support different areas of your businessWhy AI still needs guardrails, quality checks, and human judgmentUsing “useful AI” to solve real operational problems and surface issues before they become bigger onesProtecting the human side of hospitality while using AI to remove unnecessary chaosWhy the systems behind your property are what create consistency, scalability, and growth without burnout

Because the goal isn’t to automate every single thing you do.

Hospitality still requires judgment. It requires taste. It requires understanding the people who are trusting you with their vacations, celebrations, families, and time away.

Ana’s approach is a reminder that technology should create more room for those things—not replace them.

Use AI to remove the chaos. Keep the heart. And create more space to lead the business instead of carrying every part of it inside your head.

HIGHLIGHTS AND KEY POINTS:[00:50] A short introduction about our guest Ana Shapiro, and her background in real estate, transition from long-term to short-term rentals, and how she built Chilling Away