Can Airbnb redefine travel again?

Now, the company is trying to do something similar with what people do when they travel. If successful, it could be a key to boosting Airbnb stock, which has been on a roller-coaster ride for five years. But this time, the model is proving thornier and harder to scale.

Airbnb is making a renewed push into what it calls Experiences and Services—its second attempt after a 2016 effort failed to gain traction. In a major app overhaul in May, Airbnb redesigned its interface to spotlight these two categories framed by sleek visuals and trusted reviews—encouraging travelers to spend more of their trip money through the platform. Options range from surf lessons in Hawaii to foraging for truffles outside Florence to ordering a massage at your rental home.

“It’s probably one of the biggest changes in Airbnb since our founding," Chief Business Officer Dave Stephenson said in an interview. The broader goal is to turn Airbnb into a platform for the entire trip—and eventually, as co-founder and chief executive officer Brian Chesky has said, an everything app for everyday life. A former CFO at Amazon, Stephenson is playing a key role in Airbnb’s transformation—one that echoes his old employer’s evolution from an online bookstore into the everything store.

What you do on a trip is often what makes it unforgettable. A trip to Iceland, for instance, isn’t defined by the rental car. It is about the hot spring you soak in or the unforgettable whale-watching boat ride. In theory, the market is huge. Travel site Skift estimates the global tours-and-activities market is worth more than $250 billion annually.

But there are good reasons why even companies like Amazon haven’t successfully branched out into services. Unlike home rentals, which can be booked hundreds of times a year with minimal involvement, services often require someone to physically show up each time. That makes them harder to automate, standardize, or scale—and often less profitable. Hosts may also lack the proper incentives: some are resisting the idea of turning their homes into storefronts for third-party providers.

It is also rarely the first thing travelers book. Travelers tend to lock in their flight, car and accommodation early, while planning their experiences much later. This means the opportunity to capture the consumer while they are planning their trip isn’t as easy. Nils Chrestin, chief financial officer of GetYourGuide—a competitor in experiences—says the attach rate, or the share of travelers who book an experience alongside their flight or lodging, is extremely low.

Experience platforms such GetYourGuide and Viator (owned by Tripadvisor) have been in the space for decades, but scaling up has proven to be a gradual process. Bringing thousands of mom-and-pop operators online, for instance, often requires one-on-one outreach. Margins are also very thin. Last year, Viator made about $840 million in sales—but its profit margin was less than 4%, based on earnings before interest, taxes, appreciation and amortization.

Greater scale should improve profitability for the industry, as it requires fewer marketing dollars to attract recurring customers, Chrestin of GetYourGuide explains.

Stephenson says Experiences and Services could eventually be multibillion-dollar businesses, which would be a significant addition to Airbnb’s roughly $12 billion lodging business. But it will require time and sustained focus. Kevin Kopelman, an analyst at TD Cowen, notes that investors aren’t giving much credit to these new ventures yet, partly because of Airbnb’s struggles with experiences in recent years.

To draw attention to the new release, Airbnb rolled out high-profile offerings under the “Airbnb Originals" banner—celebrity-themed experiences such as a football clinic with Patrick Mahomes or an anime event curated by Megan Thee Stallion. These are designed more to generate buzz than bookings. They reinforce the brand, but they aren’t scalable businesses.

The new business is part of Airbnb’s effort to create emotional resonance, positioning itself as the antidote to the cold efficiency of Booking.com or Expedia. By layering services onto its platform, the company also hopes to capture more market share from hotels, given that many travelers still choose professional lodging for amenities like massages or on-site dining. “If we can make it easier and round out these additional capabilities for people, that’s one more reason they’ll want to stay in an Airbnb versus going elsewhere," says Stephenson.

Bob Hanlon, who runs pizza tours in New York, is part of the vision. The idea to offer tours came to him during a 2018 pizza crawl in Brooklyn. “One of the pizza bakers came out and asked us if we were on a professional food tour," he said. “That was kind of a lightbulb moment." He then turned to Airbnb to get started. It isn’t a huge profit center for him—he still maintains a separate marketing business on the side. But it is personally rewarding, he said. It adds personality to the Airbnb brand; it isn’t something a traveler might find so easily elsewhere.

That is the branding pitch. But branding only gets you so far on Wall Street. Airbnb’s brand is already a major reason its stock trades at a roughly 25% valuation premium to Booking Holdings, one that many investors are questioning as trade tensions threaten to cool the travel market.

Airbnb is betting the payoff will come in loyalty and market differentiation, and eventually power its earnings. That is a reasonable bet. But it will require patience—from travelers, from hosts, and especially from investors.

Write to David Wainer at david.wainer@wsj.com