Last-Minute Vacation Rental Platform Raises $1.5 Million From Retail Investors

Something is better than nothing — especially if you’ve invested in a vacation rental that isn’t always rented. 

More than half of vacation rental properties are empty each night, resulting in billions of dollars in lost earnings. 

But San Francisco-based Whimstay Inc. eases the pain of vacant vacation rentals for owners as it gives spur-of-the-moment travelers deep discounts on properties they otherwise might not be able to afford.

Whimstay aggregates unsold vacation rental properties and provides last-minute deals in the rapidly growing vacation rental market. The company created a marketplace for travelers wanting an Airbnb and VRBO experience but at an affordable price. 

But Whimstay’s approach is different and gives those acting on a whim to get out of town a more affordable option.

The company negotiates exclusive discounts with its property management partners and guarantees that if a traveler can find a lower advertised price on any of the major sites, it will pay for their trip — it’s had zero payouts so far.

EasyTo Use

Whimstay travelers report having positive experiences using the company’s website and app. 

“Excellent service,” Whimstay traveler Jim wrote. “Way better than VRBO and Airbnb in my experience. Everything from booking [to] payment went seamlessly.”

“Excellent app, easy to use, great deals!” Whimstay traveler Erica wrote. “I’ve been using Whimstay to book all of my vacation rentals. I find the best deals, and it’s so easy to find what I’m looking for.”

The global vacation rental market size was valued at $74.64 billion in 2021 and is expected to expand at a compound annual growth rate of 5.3% from 2022 to 2030, according to Grand View Research. 

Whimstay’s growth has outpaced that of its competitors. Within 1½ years, its app has been downloaded more than 100,000 times, and the company has listed more than 131,000 properties without spending a dime on marketing.

This year, the company released new proprietary tools on its web and app platforms: TripChat and Split It. 

TripChat lets travelers chat with friends and family directly from the Whimstay app or website. It gives them the ability to share properties react to messages and collaborate on planning a group vacation without leaving the platform. 

The Split It feature allows travelers to split the total payment for their trip between several people. 

Whimstay also makes it easy for owners of vacation rentals to list their properties on the site by filling out a form. 

Whimstay is running a crowdfunding campaign on StartEngine. So far, it’s raised $1.5 million of its $5 million goal, with 822 investors contributing a minimum investment of $249.

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