The Secret to a 65% Repeat Booking Rate

In this episode of the Hospitable Hosts podcast, we welcome Keith Clarke, who is running Encinitas Bungalows, a collection of coastal vacation homes in the heart of Cardiff & Leucadia, California. Keith manages 10 properties and uses Hospitable to streamline operations.

Chatting with Miles, Keith shares how he got into the vacation rental business and started managing properties for others, the strategies he uses to build relationships with guests and win repeat bookings, and the challenges he faces managing multiple STR properties.    

Press Play now to discover how Keith grew a successful property management business and what strategies he uses to ensure a memorable guest experience, drive bookings, and build loyalty.

Do you prefer to read the highlights? We’ve got a summary of the key takeaways below.

How Keith Started a Vacation Rental Business

Keith reveals he started a vacation rental business about 11 years ago on a whim. “I didn't know anything about the business at all,” he says. That summer, Keith bought a property, which he wanted to convert into a vacation rental. Since he had no experience with vacation rentals, he decided to outfit the place the way he would if he were traveling.

“I put in nice appliances, quality furnishings, quality bedding, and built a business having no idea of what the business is like, never even staying in a vacation rental, but I built it knowing what I like when I travel.”

Keith started with two units in a duplex, which he managed himself. “I would meet every guest at the property and get to know their story and see where they were from,” he notes. “And I had multiple guests who would come back next summer. They wanted me to block specific days for them. And we started this personal relationship, and it just evolved on its own.”

Keith had some guests who stayed with him for five years in a row. They were thinking about buying a second home, and since they live in Arizona, they asked Keith to rent it out as a vacation rental when they’re not using it. “You furnish it. I'll run it my way. We set minimum prices, figured out a management fee, and started a partnership.”

Focusing on Guest Retention to Build a Sustainable Business

Now, Keith manages 10 properties, two of which he owns. Since Keith has a regular job, he hired his friend Stacey as his “frontline person” to oversee the guest experience. She meets every guest now, as Keith used to.

Keith focuses on guest retention and repeat direct bookings to secure sustainable revenue. He says he was looking for returning guests coming to the neighborhood for a family vacation, so he wanted to build a relationship with those guests, make sure they knew about all his properties, and give them the ability to deal with him directly outside the OTAs.

“We built this business with the thought of recurring guests. We screen every guest, since we accept Instant Booking—you don't know what you're going to get. We meet every guest because we want to size them up. Why are they here? Why are they traveling? What is their purpose here? And then, once they understand our product, we say we have a website with 10 properties on it.”

Keith says that their guests are typically older couples, younger families with children, and people traveling with pets. And because their cleanliness standards are high, they really want to meet their guests and ensure they understand their rules. Keith points out that about 65% of their revenue currently comes from repeat guests, a testament to their customer-centric approach.

“When I'm on the phone, trying to reach support, and get stuck in automation hell with an AI voice—that drives me nutty. I want to talk to a person. And I think in the vacation rental business, guests are looking for that same experience. They're not used to it because nobody does that. But we do it, it sets us apart. And it's the personal connection and hearing the stories of where someone's from and where they're traveling to that makes the connection.”