History of Short-Term Rentals Filled With Arrogance and Missed Opportunities


Skift Take

The phrase "listen to the customer" is a cliche. But in the early days of the vacation rental business, the smart move was to listen to what the marketplace was saying rather than force feed it the opposite.

Looking back at the history of short-term rentals coming online starting in the mid-1990s, it's easy to see how arrogant thinking and missed opportunities left their mark, and swayed the sector's trajectory.

That's an easy takeaway from Skift's recently published three-part Definitive Oral History of Short-Term Rentals because this theme of opportunities seized and lost permeates the piece.

Expedia Looked at Vacation Rentals Through a Hotel Lens

In Part 1 of the series, Expedia founder Rich Barton and HomeAway co-founder Brian Sharples talked separately about Expedia's flawed early approach to vacation rentals, and how HomeAway nearly embarked on a similar path.

Barton recalled how Expedia acquired vacation rental startup VacationSpot in 2000. Expedia purchased the vacation rental aggregator, co-founded by a couple of Microsoft/Expedia alums, for $82 million in stock.

But Expedia's vision for Vacationspot, as Barton recalled, was to wire up the home inventory for online bookings just as Expedia was busy doing for hotels. The problem for Expedia was that vacation rental owners weren't ready to cede control of their homes to a third party, and the companies that were really gaining a foothold in the sector — such as VRBO in Colorado and Holiday Rentals in London — used a classified ad model that left reservations as a matter solely between homeowner and guest.

"I would say we took a little bit of a flawed approach instead of coming at it like VRBO did," Barton said in the oral history. "We looked at b