In This Episode

His tenant stopped paying rent. When he went to investigate, he found guest books, five-star reviews, and a listing on VRBO — for his own home.

That's how Corey Jones stumbled into vacation rentals. No business plan. No grand ambition. Just a house he couldn't sell in 2009, a tenant who saw an opportunity before he did, and a New York Times travel feature he never knew existed — about a property he owned.

That accidental beginning became Lucky Savannah, now one of the largest vacation rental management companies in one of the South's most beloved destinations, with over 400 properties across the city.

We sat down together in one of those properties — a three-story home built in the 1760s, the oldest masonry brick structure in the state of Georgia, where George Washington once stayed. It's been a colonial meeting house, a law firm, and now a meticulously restored luxury vacation rental that just won one of VRBO's top homes of the year.

In this episode, we explore:

• How a rental gone wrong became a 400-property portfolio — and why saying yes to everything was the right move early on
• What "historic luxury" actually means, and how Corey's team blends 18th-century architecture with modern amenities
• Why Savannah's hotel-first culture forced his team to operate at a higher standard from day one
• How he's thinking about AI — including a dedicated budget line item for 2026
• The case for casting a narrow net in an industry that rewards specialization
• And why the operators who stayed disciplined through the post-COVID hangover are the ones getting the calls back

Fifteen years in, Corey hasn't expanded into new markets or chased the hotel trend. He's betting that going deeper — not broader — is how you win in the long run.

A special thanks to my friends at Expedia and the VRBO team for inviting me down to Savannah to capture Corey's story in person.

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About Behind The Stays

Behind the Stays is brought to you by Journey — a first-of-its-kind loyalty program that brings together an alliance of the world’s top independently owned and operated stays and allows travelers to earn points and perks on boutique hotels, vacation rentals, treehouses, ski chalets, glamping experiences and so much more.

Your host is Zach Busekrus, Head of the Journey Alliance. If you are a hospitality entrepreneur who has a stay, or a collection of stays with soul, we’d love for you to apply to join our Alliance at journey.com/alliance.