Skift Take

Expedia and Vacasa see technology as key to improving both their businesses and the guest/owner experiences. They both face big challenges this year.

Expedia Group and Vacasa are both moving forward with tech investments to compete with other big players in the short-term rental industry. Executives from both public companies shared details about current projects during Skift’s Short-Term Rental Summit in New York on Wednesday. 

Expedia Group

Expedia Group’s existing short-term rental listing business is fragmented. For example, the Expedia website lists short-term rentals in multi-unit buildings. Vrbo, which is owned by Expedia, is a short-term rental booking site that has traditionally focused on standalone homes.

But the Expedia and Vrbo brands have separate technology stacks. Expedia Group is currently migrating Vrbo’s back-end technology onto the Expedia brand platform. The company argues that the transition will enable it to test things and iterate faster.

The brand migrated its technology to the Expedia platform last year and saw 20 percent growth in gross bookings in the first quarter of 2023.

“By being on one stack, it enables us to build things faster,” said Tim Rosolio, vice president of vacation rental partner success at Expedia Group.

Answering an audience question, he said hotels will eventually be able to sign a single contract with Expedia Group, replacing separate contracts for Expedia and Vrbo.

Expedia is already experimenting with generative AI as well, having released a chatbot recently to gather more data and the company is working to strengthen its use of the technology. 

“The important thing is we’re starting to get the learnings about how it works. Because I think the value isn’t necessarily just in the tool. It’s in how you harness the data for the tool to actually deliver something awesome for the travelers, which is hopefully the journey that we’re on,” Rosolio said. 


Rob Greyber, who joined Vacasa as CEO in 2022, has said Vacasa’s technology was lacking, and the company is addressing that with new products. 

Vacasa is a short-term rental property management company that sells about 70 percent of its inventory through third-party channels, such as Vrbo and Airbnb.

Vacasa handles short-term rentals on behalf of property owners, and Greyber said the company is working to ensure those clients have a better experience using the platform. 

“We’re obsessed … with our owner experience, and we think all of us in this industry have to be thinking about that important dimension.” 

The HomeCare product was released so homeowners can view more information about how Vacasa is caring for their homes. It includes data points like inspection reports and photos after cleaning jobs. The company plans to continue investment along these lines.

“We’ve seen terrific results from this, great engagement from it. And we’ll continue to invest behind this and other initiatives that we think make the experience of vacation rentals better for our homeowners, better for our guests, and better for our teams in the field,” Greyber said. 

Greyber is working to help Vacasa rebound from a from a lot of homeowner turnover. The company did two rounds of layoffs since Greyber became CEO. Nasdaq recently informed Vacasa that it faces delisting if its stock price remains below $1 per share for a certain period, but Greyber said that won’t happen.

Now, the company is focused on long-term improvements.

“I think there’s a hard problem in this industry to solve, and I think we are at the nexus of that,”  Greyber said. “And it’s a problem that is best solved with technology-enabled services, with the hospitality where you’re using the technology that’s available to help the people that are the closest to our guests and to our homeowners.”


Dwell Newsletter

Get breaking news, analysis and data from the week’s most important stories about short-term rentals, vacation rentals, housing, and real estate.

Have a confidential tip for Skift? Get in touch

Tags: artificial intelligence, expedia, expedia group, generative ai, short-term rentals, skift live, skift short-term rental summit, vacasa, vacation rentals, vrbo

Photo credit: Rob Greyber, CEO of Vacasa (left), and Tim Rosolio, vice president of vacation rental partner success at Expedia Group, joined a panel moderated by Dennis Schaal. Ryan Bourque / Skift

Up Next

Loading next stories