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Now that Expedia Group has its tech stack in order, Vrbo plans to launch sponsored listings, and Expedia is likely to follow. Vrbo listings on Expedia are operating at a $1 billion annual run rate.

Vrbo thinks the sponsored listings will be a substantial financial “unlock” for the group. Airbnb, meanwhile, has talked up sponsored listings, but hasn’t launched them to date. It’s only a matter of time before Airbnb gets around to it, as well.

WEX + SKIFT

Airlines' payment infrastructure is becoming a key growth bottleneck. Without updating it, airlines risk falling behind on global expansion and digital retail ambitions.

EDITOR’S PICKS

Vrbo Is Launching Sponsored Listings — with Expedia.com Placements to Come

June 10, 2026

Vrbo and Expedia are seizing an obvious opportunity in vacation rental sponsored listings. Airbnb will get there eventually too.

Skyscanner CEO on Agentic Booking and the Future of Flight Metasearch

June 8, 2026

Given Skyscanner's leading global footprint in flights, it isn't hard to envision an LLM extracting it from Trip.com Group to accelerate building a travel vertical.

Booking.com CTO: The New Bottleneck Is Teamwork

June 3, 2026

Many of the pressing issues in AI implementation are organizational, not technological.

Expedia Tech Exec on Build Versus Buy: Keep Customer Data Close

June 3, 2026

Acquiring a shiny company to boost your AI ambitions may seem appealing, but buying can sometimes set a company back.

After Sonder’s Collapse, Francis Davidson Returns With an AI Travel Agent

June 2, 2026

Another AI travel agent might not be news. One built by the founder of Sonder, with something to prove, is.

Expedia Names Ex-Pinterest Exec to Lead Ads. The Pitch: Real Bookings, Not Intent.

June 1, 2026

Expedia's advertising program has one thing that Google and Meta can't offer — confirmed bookers. As such, advertisers can target travelers with set plans and try to entice them to book additional products.

Jamie Dimon Says Moats in Banking Are Temporary. Sounds Like Travel.

May 29, 2026

In travel, as in banking, the moat you're defending today is probably shallower than you think. And it's likely someone is already digging around it.

Expedia x IShowSpeed: Why Brands Are Doubling Down on Creators

May 27, 2026

Expedia's IShowSpeed partnership is another signal that creator marketing has moved from experiment to core strategy among travel brands — though it’s not yet clear how its social media impressions are converting to bookings.

Airbnb Invests in WeRoad — and Hired Its CEO to Lead Hotels

May 27, 2026

Airbnb has struggled to scale experiences. Investing in WeRoad — and hiring its CEO — is Chesky's preferred move: partner first, potentially acquire later.

Airbnb Names Booking.com Veteran in Hotel Leadership Shakeup

May 26, 2026

The hotel leadership shuffle represents somewhat of an about-face for Airbnb as it opts for a leader with online travel agency experience rather than a hotel brand track record. Still, these are early days for Airbnb hotels, and there is plenty of time to get things right.

SKIFT PODCAST NETWORK

In this clip, Vipul Hingne explains Booking’s core principle for AI (and any tech at scale): shipping is not enough. If you deploy something without the ability to operate it, it won’t work.

SKIFT TRAVEL 200

How are public travel tech companies performing around the world? The Skift Travel 200 pulls the data you need to know to understand the market. Paid subscribers get full access here.