Discounts on Last-Minute Short-Term Rentals Could Be the Next Big Thing

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Will startup Whimstay be the next Hotwire or Priceline in offering last-minute rates at a discount for vacation rentals?

That speculation is premature, for sure, but the problem Whimstay is solving will indeed find a significant niche in the short-term rental sector.

Ben Jamshahi, co-founder and CEO of Whimstay, a San Francisco-based startup, said the company contracts exclusively with hundreds of property managers to offer discounted rates of 15-60 percent, usually within 21 days of the stay. He said in some cases guests can book just one day before starting their trips. 

Whimstay also offers much longer booking windows, but without discounts as significant as in the 21-day timeframe. “Within 21 days is the sweetest,” Jamshahi said.

Whimstays’ publicly disclosed partners for reduced rates on expiring inventory include Vacasa, Inntopia, Natural Retreats, and Best Beach Getaways. In addition, Whimstay, which also offers vacation rentals at more traditional retail rates, has integrated with a variety of property management systems, including Escapia, V12.net, Streamline VRS, and Hostfully. 

It remains to be seen what kind of traction Whimstay might eventually command. Property manager Evolve, which has been around for more than a decade, had seven times Whimstay’s website traffic last month, for example, according to SimilarWeb. It was 672,000 visits for Evolve versus 104,000 for Whimstay.

Founded in 2018, Whimstay officially launched this year in January, Jamshahi said, and so far it has only a half-dozen employees and is bootstrapped with friends and family money.

Regardless of Whimstay’s ultimate fate — and more importantly — what’s clear is that the selling of distressed inventory — or providing discounts on vacation rentals that would otherwise go unoccupied at full retail rates — should have a bright future in this hot sector.

Unlike Hotwire and Priceline’s rest-in-peace Name Your Own Price bidding for hotels, Whimstay doesn’t need to do much to shield vacation rental partners from the embarrassment of dealing with Whimstay offering their vacation rentals rates at lower prices than the property manager or owner’s own websites. That’s because there are relatively few branded vacation rentals these days so few consumers would easily see that the same property on Airbnb or Booking.com might be selling for $300 per night while Whimstay might be selling it for $200.

Given the growing popularity of vacation rentals among families, couples, singles, and digital nomads in particular, the lure of a good deal via discounted last-minute rates — what Jamshahi repeatedly called the Overstock model —should be able to find an important place in the sector.

We took an admittedly limited look at Whimstay’s value proposition when viewing three vacation rental stays within a couple of weeks from last weekend in Hilton Head, South Carolina; Martha’s Vineyard, Massachusetts; and Pigeon Forge, Tennessee. 

In all but one instance — the property manager’s own website in Pigeon Forge, Tennessee — Whimstay offered discounts compared to nightly rates on Vacasa, Booking.com, Airbnb, Expedia, Homes & Villas by Marriott International, and Tripadvisor ranging from around 8-29 percent.

In that Tennessee example, Whimstay’s total rate for the 2-bedroom Stone’s Throw cabin in Pigeon Forge for a June 15-17 stay was $766 and the property manager, Bear Tootin Rustic Vacations, had the place for roughly the same rate. However, Whimstay’s rate was 24 percent lower than Tripadvisor’s and 29 percent lower than Expedia’s on the same dates.

Whimstay’s rate of $1,370 for vacation home Harbourside #7123 on June 5-11 in Hilton Head, South Carolina was $1,370, and that was lower than on Vacasa.com (by 8 percent), Booking.com (16 percent), and Homes & Villas (19 percent).

In Oak Bluffs, Massachusetts on Martha’s Vinyard, you could book the 2-bedroom Island Inn #41G for today (May 31) through June 3 for $1,374 on Whimstay. That would be a savings versus Vacasa (8.2 percent), Homes & Villas (24 percent), and Airbnb (27 percent). 

Although Whimstay indeed provided savings for last-minute bookings compared with the vast majority of websites, I didn’t find Whimstay’s excessive boasts about the amount of purported savings particularly useful — or true.

The website touts that you can use to “save up to 60% on last-minute rentals.” We didn’t see anything even approaching that amount. 

Whimstay’s website stated that the $1,374 rate for the Martha’s Vineyard 2-bedroom “saves $746.10” when it was merely a $113 savings versus Vacasa, and $374 lower than Airbnb for the same place on the same dates. Whimstay uses a complex formula to calculate those alleged savings. Although the hyperbole might convince more people to book, Whimstay’s credibility takes a hit.

Whimstay, which only offers properties from professional managers for now, has a few features beyond discounted nightly rates that help it stand out. 

For a fee, prospective guests can turn what would have been nonrefundable bookings into refundable ones for maximum flexibility. It also has a Tripchat feature to enable a group to text together about their trip, and another feature enables guests to split the cost of the stay.

Jamshahi said Whimstay is on target to reach its first $1 million in revenue in the next 60 to 90 days, and that the business is getting “insane” traction after having really done its consumer launch at the beginning of the year.

“Whimstay is pursuing an interesting niche,” said Brian Egan, co-founder and CEO of property manager Evolve. “They face a significant challenge in establishing differentiated value for both sides of the market. Consumers have to see enough high quality inventory available last minute at steep enough discounts to change behavior. Likewise, suppliers have to believe those bookings are truly incremental to what they can generate by leveraging sophisticated revenue management on established OTAs (online travel agencies) and direct brand sites. That’s a high bar.”

Egan said it’s an “open question on whether it will work, but I view their effort as another promising sign of mainstreaming in our category.”

Whimstay might have advantages as an early mover in the category, but it’s hard to see how they would be daunting to a larger and more amply resourced competitor.

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