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This fast-growing S.F. vacation rental startup is staking a claim on last-minute travelers

- By Alex Barreira

17 Nov 2021

A young Bay Area hospitality startup for booking last-minute vacations is hitting a growth spurt, adding 10,000 new listings each month and a new headquarters in San Francisco while positioning itself for hosts as a no-brainer add-on to Airbnb.

Whimstay, which settled into offices on California Street last month, has just 13 full-time employees but more than 107,000 properties on its platform and 100,000 smartphone app downloads, CEO Ben Jamshahi says. He and co-founders Alex Alioto and Kamesh Jasani founded the company in 2018 around the simple premise that short-term rental properties are inefficient — they are occupied less than half of their available nights on average — and hosts would be happy to offer a last-minute discount to avoid an empty room.

All vacation rentals on the platform are only bookable 21 days or less before the date of stay. Whimstay offers travelers an exclusive discount on the stay, pre-negotiated with the property owner, and takes a 3% to 5% commission from each.

Occupancy was an issue Jamshahi encountered himself trying to monetize vacation homes in Maui and Truckee on platforms such as Airbnb, VRBO and Booking.com, and finding "the best I could do was 50%." According to short-term rental analytics firm Link AllTheRooms, the average occupancy rate of an Airbnb in the U.S. was just 48% prior to the pandemic in 2019.

"They haven't been able to solve this issue of the overstock model," he said, of existing vacation rental platforms. "Once that day is expired you can't bring it back."

Whimstay acts as the "merchant of record" in the transaction, collecting travelers' vacation deposit in escrow and transferring it to the property host within 24 hours of guest check-in. It becomes a "win-win" for everyone, the CEO told me, when guests save as much as 60% off their stays and hosts have more rooms filled.

"We believe in the gift of spontaneity," Jamshahi said. "We want to bottle the thrill of last-minute adventures and ship it to the masses."

And perhaps the best part of Whimstay from the perspective of property owners is its lack of exclusivity — property owners don't need to take their listings off other platforms to have a Whimstay listing available, a kind of contingency against unbooked rooms, and an invitation to cost-conscious travelers (hello, Gen-Z?) that may feel priced out of hotels and Airbnb.

After starting 2021 with around 18,000 listings and growing the company through word-of-mouth, Whimstay struck oil this year via integrations with websites such as TurnKey Vacation Rentals and property management systems Streamline VRS, Escapia, V12.net, and "everyone and anyone we could," Jamshahi said, ballooning the portfolio by another 90,000 by the end of October.

Jamshahi said the company has raised some private capital (declining to disclose the amount) but that the company's goal has been to achieve critical mass — listing about 20% of U.S. vacation rental homes on the platform — before more aggressively pursuing venture funding. Still, this month Whimstay has raised more than $369,000 on equity crowdfunding platform StartEngine, with a target goal of $1 million.

All this, the CEO says, is only the beginning. Whimstay plans to debut a new feature on the platform in January which the company has recently patented. Jamshahi declined to elaborate on what it entails but said, with characteristic enthusiasm, "I promise you this — it's going to change the way people approach booking. Not just vacation rentals, but other things."

About Whimstay

Whimstay is the leading marketplace dedicated to last-minute vacation rental deals. Whimstay provides property managers a new sales channel to liquidate expiring inventory, increasing occupancy and income. Our website and app are a destination for travelers to book last-minute vacation rentals on thousands of properties throughout the United States at significant discounts, typically saving hundreds of dollars per booking. Whimstay was founded in 2018 and is based in Wilmington, DE. To learn more, visit whimstay.com.

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