Brad Callahan and Vantage Vacation Rentals

One owner's experience selling his vacation rental business to Vacasa.


Before choosing to sell the business he built from the ground up, and before the internet changed the short-term rental industry forever, Brad Callahan fell in love with a beach.

Ocean City was the place to be when I was growing up,” he says. “It was a summer highlight to go there for a day, a weekend, or the occasional week. In college, I worked in Ocean City for two summers, making lifelong friends and deepening my love of the community.”

After studying the local rental scene, Brad saw an opportunity to pioneer a new standard of secondary accommodations in the legendary Maryland vacation spot.

“I was underwhelmed by the customer service I had seen at the variety of rental companies I’d worked with over the years,” he says.

So, in 2007, Brad founded Vantage Vacation Rentals. The business built its reputation by blending thoughtful services—like delivering daily newspapers and gym access—with next-gen software. Eventually, he grew Vantage to serve over 500 homes in this beachfront community.

A change of the tide

But as much as he loved collaborating with his talented team, inconsistent vendors and staffing challenges were persistent headaches. And all the while, he had to keep up with the revolutionary changes in the vacation rental market online.

“The key to our operation was to ensure that the vacation rental amenities were equivalent to what people have at home,” he says. “In other words, I didn’t want people to feel like they were sacrificing anything by being on vacation. Lately, that means Smart TVs, keyless check-in options, a better online presence, and more communication with homeowners and guests.”

Through the Vacation Rental Management Association, Brad noticed that Vacasa was increasingly becoming a major player in the ever-more-demanding industry.

“[I’ve] been impressed by how Vacasa stayed true to the mission of growth through acquisition—getting stronger and stronger. They’ve added some top-tier talent to the team and the acquisitions have gotten bigger and smoother,” he says.

“But when the original offer came over from Vacasa, I rejected it. I wasn’t sure this was the right fit for my staff, for my homeowners, or for me.”

His concern?

“It was important to me that my reputation from building Vantage not be squandered in a transition,” he says. “I was very proud of what we were able to do with Vantage—I still see tons of opportunity in the market. Someone needed to continue to drive the improvement that the OC market hungers for.”

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When I analyzed what Vacasa brought to the table, they checked a lot of the boxes for services that I wanted for my homeowners. I am so confident that Vacasa is on the right track that I volunteered to be the first Vantage homeowner to list my properties with them.
—Brad Callahan, owner of Vantage Vacation Rentals

Uncharted waters

Still, Brad decided to continue the conversation with our team at Vacasa. And as he saw more of the business, he understood that joining forces with Vacasa could help Vantage deliver in the long run.

“I was at a crossroads to either sell or reinvent Vantage—new website, new software, and new services,” he says. “When I analyzed what Vacasa brought to the table, they checked a lot of the boxes for services that I wanted for my homeowners. I am so confident that Vacasa is on the right track that I volunteered to be the first Vantage homeowner to list my properties with them.”

So, he took the leap and hired a broker to help him negotiate the sale.

“[The broker] helped ease my mind on the right sales price, partner, and transition terms,” he says. “Vacasa is a great buyer, but I wasn’t ready to be a good seller until the broker stepped in.”

Vacasa’s transition team exceeded his expectations. He felt he could count on solid communication from our HR support team and acquisitions manager.

“The trust was strong enough to trigger a deal,” he says. “Vacasa was thoughtful in the employee transition process and gave everyone the opportunity to meet, discuss, and move into the Vacasa framework. I’m also impressed with the owner relations team. They have been patiently talking to each homeowner to address questions and concerns.”

And great communication on Vacasa’s end was doubly important—especially during the unpredictable pandemic rental market.

“We saw a ridiculous uptick in vacations during the second half of 2020. And that blistering pace continued for the first three months of 2021, right up to the day of our transaction. Each week, our marketing, reservations, and leadership teams would get together and marvel at the record-setting pace for bookings,” he says. “The staff is in for an extremely busy summer, and the support and processes with Vacasa should be a win for the team.”

New horizons

Now, Vantage homeowners are settling into management with Vacasa. And while some of his homeowners miss a few aspects of old Vantage, most are looking forward to enjoying the benefits of partnering with Vacasa—Brad included.

“Vacasa has a strong online and SEO presence,” he says. “[We] really appreciate the owner portal and the ease of finding details and data on individual properties. Changes like no marketing fee, shifting to guest-paid cleaning fees, and a free photo package were all benefits that owners were very excited to receive.”

But more than the benefits he’ll enjoy as a Vacasa homeowner, Brad’s looking forward to getting back to what matters most: his family.

“COVID had me spending more time inside of Vantage than ever before—and it had a dramatic impact on my time away from family,” he says. “Once the sale was complete, I was able to reconnect and thank my wife and the kids for their patience over the last year.”

Thinking of selling your business? Brad offers this advice:

“Whether you use a broker or not, it has to start with your motivations—why are you in the business? If you are contemplating a sale, visualize your ideal outcome and then structure the deal carefully to achieve your objectives,” he says. “My goal was to simplify my life. And selling Vantage to Vacasa has certainly done that.”

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