Booking Holdings Plans $100 Million for Second AI Startup, Vayo

Booking Holdings has launched a second AI-native startup, Vayo, aimed at travellers who book across many brands, including Booking's competitors.

Vayo opened in private beta on October 14 with a waitlist at vayo.com. Booking plans to invest $100 million, subject to continued product progress and market conditions. It follows Lola, another internally funded AI venture unveiled about two weeks earlier. Booking has given both a "greenfield" mandate to build businesses beyond its established brands.

Vayo is meant to be where a traveller manages an entire trip, including reservations made elsewhere. It starts by connecting to a user's inbox and pulling in confirmations from any brand, Expedia and Booking.com among them. It builds a profile of how the person travels, watches bookings for price drops, flags gaps in an itinerary and warns when a flight change puts a hotel check-in or dinner reservation at risk.

CEO Mike Fridgen described the target user as a high-frequency leisure planner who organizes trips for family and friends with spreadsheets and documents. Vayo's research puts this group at a single-digit share of travellers but 27% to 30% of spend.

At launch, Vayo organizes and monitors trips rather than booking end to end. OpenTable reservations work inline, and Fridgen said direct booking should begin within weeks through integrations. For now, most of what Vayo surfaces sends travellers elsewhere to transact.

Booking is also running AI work inside Booking.com, Priceline, Agoda and Kayak. It frames the approach as portfolio experimentation rather than a single bet on one AI interface. Skift reported the details.

For operators, the question is who owns the guest relationship once an assistant sits above every booking. A tool that sees confirmations from all channels could shape where travellers rebook, and Vayo's move to direct booking is the step to watch.