A groom-to-be was scammed out of £1,500 after Booking.com's artificial intelligence assistant told him to pay for a non-existent holiday villa by bank transfer.
Alfie Learmouth, 27, booked a five-day romantic trip to Positano on Italy's Amalfi Coast to propose to his girlfriend of nine years, Jordan Bland.
Before departing on September 3, the sales project manager received a message claiming to be from the villa host demanding full payment in advance via direct transfer.
Concerned about fraud, Mr Learmouth consulted Booking.com's AI Trip Support chat tool, named Dot, to verify whether the payment method was genuine.
The automated agent, which introduced itself as "still learning", advised him that "yes, the property requires full payment via bank transfer before your arrival".
Reassured by the official support tool, he transferred the £1,500 balance, only to receive a message on the morning of their flight claiming a burst pipe had flooded the villa and cancelled their stay.
When the couple travelled to Positano and tried to locate the property, they discovered it did not exist.
Mr Learmouth, from Bexley, south-east London, said: "It was absolutely horrendous and one of the most stressful things you could ever go through.
"I looked on Booking.com and I found this really nice private villa and it had verified reviews, all looked really good so I went ahead and booked it.
"An hour before we left home bags packed, ready to go and just about to call a cab to head to the airport, I get an email from the property saying 'we can't host you anymore due to a burst water pipe'.
"It was then when I was like 'this is a scam'.
"I'm on the phone to Booking.com saying exactly what's happened and they lead with 'oh no, you've just cancelled it'.
"We were frantically trying to book somewhere just before we leave."
Their disruption worsened upon arriving at Naples Airport, where British Airways staff informed passengers that luggage had been left behind.
"We landed on a full BA flight and there's an announcement from the captain to say a few bags haven't made it and I just knew it was going to be us with all the luck we had," Mr Learmouth said.
"We get off the plane and five bags come out of a 300-person flight."
The couple had to spend around £600 on replacement clothing, makeup, and essentials, including a £75 taxi ride to a shopping mall in Pompeii.
"Luckily I had the engagement ring in my hand luggage," he added.
"We essentially wasted our whole first day going back and forth to the airport and buying clothes.
"We actually tried to find the accommodation because we were staying in Positano and it doesn't exist.
"We had dinner at the restaurant opposite where it should be and spoke to the owner of the restaurant.
"We showed him pictures and he said to us 'someone was here a month ago with the exact same photos in your same situation'."
Despite the ordeal, Mr Learmouth proposed as planned during a private boat trip on September 5, and Miss Bland accepted.
"I'd booked a boat to go on as a surprise," he said.
"I popped the question and that was amazing for the rest of the evening, the rest of the holiday was really, really good.
"This just put a massive dampener on the whole holiday. I'm not asking for compensation, I'm asking for the bare minimum of my money back.
"It's not a couple hundred quid, it's thousands and thousands of pounds that they owe me not because of any fault of my own."
Booking.com apologised for the experience and confirmed it has removed the listing and begun issuing a refund.
A spokesperson for Booking.com said: "We were sorry to hear about this customer's experience.
"On the day of the cancellation, we worked with the customer to help resolve the situation, with the trip beginning on the same day, as planned.
"Should a customer have any concerns about a payment message, we encourage them to review the payment policy in their booking confirmation.
"In this case, the confirmation explained that payment would be taken by card rather than by bank transfer.
"We can confirm that we are processing a full refund, and the property is no longer listed on our platform."
A spokesperson for British Airways said: "We've apologised to our customer for their experience and were in touch to swiftly resolve the issue to ensure they were not left out of pocket."
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