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Expedia may have taken on its biggest challenge yet with this morning’s announcement that will acquire vacation rental business HomeAway for USD3.9bn in cash and stock.

“We have long had our eyes on the fast growing ~$100 billion alternative accommodations space and have been building on our partnership with HomeAway for two years,” said Expedia CEO Dara Khosrowshahi

“Bringing HomeAway into the Expedia, Inc. family and adding its leading brands to our portfolio is a logical next step.

” We look forward to partnering with them to accelerate their shift from a classified marketplace to an online, transactional mode.”

And there’s the challenge.

HomeAway is a mish-mash of technology, a reflection of the large number of acquisitions that have been made over the past few years to create the present company.

Live, real-time property bookings remain an elusive goal for HomeAway, which is essentially a holiday rental listings business, albeit a very large one with 1.2 million properties on its sites.

In contrast, sector leader Airbnb offers is very tech savvy connecting its homeowners directly to consumers.

Brian Sharples, Chief Executive Officer of HomeAway,  said HomeAway “has been moving toward a fully online bookable marketplace and closer to the type of transactional business model with which Expedia has tremendous experience.

“We’re eager to benefit from Expedia’s distribution, technology and expertise,” Mr Sharples said.

The transaction is expected to close in the first quarter of 2016.

The HomeAway portfolio includes HomeAway.com, VRBO.com and VacationRentals.com in the United States; HomeAway.co.uk and OwnersDirect.co.uk in the United Kingdom; HomeAway.de in Germany; Abritel.fr and Homelidays.com in France; HomeAway.es and Toprural.es in Spain; AlugueTemporada.com.br in Brazil; HomeAway.com.au and Stayz.com.au in Australia; Bookabach.co.nz in New Zealand, and Asia Pacific short-term rental site, travelmob.com.

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