Airbnb Wants to Be the “Amazon of Travel”, and It’s Spending Hundreds of Millions to Get There

Airbnb doesn’t want to be the app you open twice a year to book a place to sleep. CEO Brian Chesky is openly chasing something bigger: turning Airbnb into a one-stop shop for travel, an “Amazon of travel” where lodging is just the starting point.

To pull it off, the company says it will pour “hundreds of millions of dollars” into upgrading its app, expanding services and experiences, and pushing users to come back weekly, not just when they’re ready to hit “Book.” The pivot throws Airbnb into even more direct competition with travel giants Booking.com and Expedia, which have long sold travelers a bundled, end-to-end trip.

Airbnb’s pitch is different: less cookie-cutter, more personal. But as it tries to own more of the vacation planning process, the move raises familiar questions about quality control, the role of hosts, and the pressure short-term rentals can put on cities.

Chesky’s goal: from “twice a year” to “twice a week”

Chesky has acknowledged a hard truth about Airbnb’s business: most people use it “once or twice a year.” That’s great for big-ticket bookings, but it’s a weak position in a world where apps fight to become daily habits.

Airbnb’s new ambition is to become something closer to a reflex, an app people check “once or twice a week.” That means building reasons to open Airbnb before a trip, during a trip, and after a trip, not just at the moment someone needs a bed.

The company’s strategy mirrors the classic platform playbook: start with one core product, then expand outward until customers stop shopping around. Airbnb wants travelers to stay inside its ecosystem instead of bouncing between Google searches, guidebooks, messaging apps, and separate booking platforms for tours and activities.

Hundreds of millions more for experiences, add-ons, and a smoother app

Airbnb says it’s investing hundreds of millions of dollars to turn its booking app into a broader travel platform. That money is aimed at new features, tighter integrations, and the heavy technical lift required to make search, payments, customer support, and trip management feel seamless on mobile.

The most visible push is toward “Experiences” and other add-on services, things to do, moments to book, and travel-related services that can be layered onto a stay. The promise is convenience: fewer apps, fewer tabs, and fewer chances for travelers to drop out of Airbnb’s funnel.

Airbnb is betting its scale gives it an edge. The company says it lists about 4.5 million places to stay across 81,000 cities, and that more than 300 million travelers have used the platform. It also says hosts have earned more than $41 billion in supplemental income over the past decade, part of Airbnb’s argument that its model spreads money beyond traditional hotel chains.

But expanding beyond lodging also expands the ways things can go wrong. A rental can already spiral into disputes over cleanliness, keys, neighbors, or accuracy. Add tours, services, and other third-party offerings, and Airbnb has to enforce standards and resolve conflicts across a much wider range of problems, without breaking the “easy” experience it’s selling.

Booking and Expedia have millions of hotels; Airbnb has “a few thousand”

Airbnb’s shift is also an attack on the home turf of Booking.com and Expedia, two of the biggest online travel agencies Americans use to compare hotels and build trips quickly. Those platforms list millions of hotels with standardized amenities and easy side-by-side comparisons.

Airbnb, by contrast, is still a smaller player in traditional hotels, described here as offering only “a few thousand.” That means it can’t win a pure inventory war. Instead, it’s trying to compete by wrapping lodging in a broader travel experience and keeping customers engaged between bookings.

The difference shows up in how people plan a quick getaway. For a three-night city trip, Booking can serve up a long list of similar hotels with predictable services and flexible cancellation policies. Airbnb can offer standout homes and unique stays, but it has to work harder to reassure travelers on consistency, safety, and what happens when plans go sideways.

There’s also a brand risk: Airbnb built its identity on uniqueness. The more it scales and standardizes to compete with the big travel marketplaces, the more it risks sanding down the very quirks that made it feel different in the first place.

The real fight is attention, and who owns the trip-planning habit

Underneath the strategy is a blunt reality: attention is expensive. Travel companies flood TV, streaming, social media, and search ads to make sure their app is the first stop when someone starts dreaming about a trip.

An app people open once or twice a year is vulnerable. Airbnb wants to create more “micro-moments”, checking ideas, browsing activities, saving options, so travelers think “Let me look on Airbnb” long before they’re ready to pay.

If Airbnb succeeds, it could squeeze smaller players: local tour operators, niche activity platforms, even tourism offices that help visitors plan. Once a “super-app” becomes the default interface, with your account, payment info, and preferences already loaded, everything outside that ecosystem can become harder to find.

And there’s a bigger civic concern. A platform that makes it easier to stack activities and concentrate demand can also intensify tourism pressure on specific neighborhoods and hotspots. Airbnb has already been at the center of political fights in major cities over housing availability and short-term rental rules. Becoming more powerful, and more central to how people plan trips, could amplify those tensions.

Airbnb is selling a story, not just a room

Airbnb’s edge has always been emotional as much as practical: it sells the idea of a more memorable, more personal trip. The company leans into the “experience economy,” where what you’re really buying is the story you’ll tell afterward.

That’s why Airbnb keeps spotlighting unusual stays and highly produced, limited-time promotions designed to make the platform feel magical and distinct, more than a commodity marketplace for beds.

In France, the market for “unusual accommodations” has been cited as growing, with revenue estimated at about €430 million in 2023, roughly $465 million, across about 1.2 million overnight stays. Airbnb is using that kind of demand signal to justify expanding beyond rentals into experiences and services.

The challenge is threading the needle: keep the promise of authenticity while industrializing the product enough to compete with the biggest travel platforms on earth. If Airbnb can pull it off, it becomes the remote control for travel. If it can’t, it risks becoming just another crowded marketplace, bigger, busier, and less special.