The vacation rental startup Wander is using AI to power a next-generation concierge service.

Wander, which manages and rents out dozens of high-end vacation homes across the country, aims to deliver the same level of reliable luxury as a top-of-the-line hotel chain. And to eliminate some of the confusion people can experience navigating idiosyncratic rentals booked through platforms like Airbnb or Vrbo, Wander enables guests to control features like door locks, lighting, and temperature through one smartphone app.

And because Wander manages each of the homes it rents, rather than simply acting as a marketplace or travel agent, it can provide a comprehensive home manual documenting other features, from how to stargaze through in-home telescopes to how to heat up grills and hot tubs. In addition to browsing those manuals directly, guests can chat with an AI-enabled concierge loaded with site-specific data, so it’s able to answer questions from where to find the TV remote to where to go for dinner. 

The automated concierge can also field maintenance requests if there’s a problem at a property—or, if need be, transfer questions to a human operator, says founder and CEO John Andrew Entwistle.

“If for whatever reason you seem frustrated, then it’ll automatically transfer to a human, to make sure that you’re getting the best quality of care,” he says.

AI also plays a hand in dispatching tasks to local vendors if there’s a problem like a leaky faucet, automatically creating a service ticket and assigning it to a Wander-approved contractor. Approving a final quote for the repair is still handled by a human—”We don’t have the AI spending money for us quite yet,” Entwistle says—as is interviewing and onboarding the local vendors in the first place. But enlisting the help of AI helps make it possible to manage properties across the country at scale, he says.

“Historically, you would have to have literally dozens of property managers, basically calling and managing and scheduling and all those different things,” he says. “Our thesis at Wander was, could you use software to automate large swaths of the industry, from the actual scheduling to the vendor payouts to the ticket systems.”

So far, the company is expanding rapidly, ending last year with about 30 rentals and expected to finish 2024 with around 200. Entwistle projects the company could have more than 600 locations under management by the end of next year.

“I think the other companies in the space have failed at the higher end,” says Joshua Browder, the CEO and founder of DoNotPay who’s also an early Wander investor. “I think they’re going to take a serious chunk of this higher end of the market.”

To be sure, Wander rentals aren’t cheap, with some properties renting for thousands of dollars per night and minimum stay length requirements in place. Indeed, the company boasts of its high-end clientele on a web page recruiting property owners to place their houses under Wander management.

“70% of Wander guests are affluent, with net worths exceeding $1M,” according to the web page. “Wander’s audience is primarily composed of CEOs, founders, executives, software engineers, and individuals working predominantly in the tech sector.”

But Entwistle emphasizes that friends, colleagues, or business partners sharing a house can split the bill, so prices aren’t necessarily that much higher per person than other rentals or hotel options. The company also uses AI and data science to scour real estate listings for available rentals it makes sense to manage, estimating potential revenue and highlighting eye-catching properties.

“It’s certainly made what you would expect to be an unfathomable, needle-in-a-haystack task, something that now software can do,” Entwistle says.

Wander does have to work with municipalities to make sure it’s compliant with short-term rental laws and paying applicable taxes, though Entwistle says Wander’s large, luxury rentals are less likely to be affected by regulations aimed at preserving affordable housing in tight real estate markets. The company also doesn’t operate in urban areas, where restrictions are tighter and, Entwistle says, hotels typically have the market locked down.

But, Entwistle says, the AI concierge is likely to continue to gain new capabilities, including helping users book dinner reservations, flights, and rental cars, meaning it may come to assist travelers even when they’re not staying in a Wander rental.

“My real goal is for everyone to have this AI travel agent right in their pocket,” he says.