Building a Resilient Short-Term Rental Business

In this episode of the Hospitable Hosts podcast, we welcome Eli Stoughton, Owner of Lahaina Studio. A lawyer by training, Eli started his STR business 8 years ago. Now he self-manages his three vacation rentals in Lahaina, Maui, Hawaii, and uses Hospitable to streamline operations and save time.

In the episode, Eli shares how he got into the vacation rental industry, the lessons he has learned over years of hosting, and how he uses short-term rental property management software and AI tools to improve efficiency and grow a sustainable business.

Press Play now to discover how Eli turned his Airbnb side hustle into a full-time short-term rental business, and how Hospitable helps him run his business on autopilot.

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

How Eli Started His Short-Term Rental Business

Eli says he started hosting while he was a lawyer living in Chicago. He decided to rent out his “lovely apartment with a view of Lake Michigan” on Airbnb while he was traveling in the summer.

“I thought, it’s such a shame that this place is going to be vacant—why not make some money off of it as well? So I put it up on Airbnb, and I was very pleased by how smooth and easygoing it was, relatively speaking, and it was a good way to earn some money. I always had an eye on it as a possible exit plan, something to do with future investments. And once I got to a certain financial threshold, I decided to make the jump.”

In 2018, Eli got his first four short-term rentals in Lahaina. He also owned short-term rentals in Joshua Tree, California, and Stowe, Vermont. So he has experience running vacation rentals in different markets.

About Hospitable Community

Eli isn’t just a Hospitable user; he is an active member of the Hospitable Community, where hosts can ask questions, help others to get answers, share tips and best practices, and connect with hosts from around the world.

“I was probably one of the first or second individuals to invest in the company,” Eli explains. “So being an investor in Hospitable has given me a bit more buy-in when it comes to staying involved in the community.”

He believes the online Community is a great resource “that everybody should check out” if you have questions about Hospitable or running short-term rentals in general.

“It doesn’t require actual account access the way it would for a Hospitable Support member to help you with something. You’ll often get people, such as myself, who will answer questions pretty thoroughly and relatively quickly,” Eli emphasizes.

About Listing on Multiple Channels

Eli started his short-term rental business on Airbnb, but has now expanded to Booking.com and Vrbo. He emphasizes the importance of listing short-term rental properties on multiple platforms to reach a diverse audience and protect your business from risks like algorithm changes or shifting platform policies. “Whenever you're completely dependent on one platform, one little change in their algorithm or their focus could impact you tremendously,” Eli says.

“Airbnb is wonderful, but at the end of the day, they're running their own business,” he notes. “They have tremendous power, because they’ve done a great job of aggregating so much demand. But you really don’t want to be completely dependent on them. And the best time to act is now: if something changes a year or two from now that negatively impacts you, you'll want to have your properties listed on other OTAs, Vrbo, and Booking.com, and on a direct website as well. And you want it all operating for a while, so you have at least a few positive reviews there.”

Eli shares his experience of starting on Vrbo and Booking.com. He says that creating listings manually across different sites feels “tremendously complicated” because the sites have different settings. But for him, creating listings on Vrbo and Booking.com was easy because he did it through Hospitable.

“It’s never been a better time to take advantage of that software, because with the new Vrbo Partner Integration, things are going much more smoothly, I think. And with the Hospitable Essentials plan, which is the free plan, there’s no reason not to give it a try.”