Whimstay Is Redefining the Last-Minute Vacation Rental Market

By Robert White, Editor-in-Chief

In a crowded marketplace dominated by giants like Airbnb and VRBO, it can be challenging to carve out a niche. Yet, in 2018, Alex Alioto, along with his co-founders Ben and Jim, did just that with Whimstay—a unique travel marketplace focused on solving the problem of expiring inventory in the short-term rental market. What began as a solution for a problem faced by Ben, a successful entrepreneur who owned multiple short-term rental properties, has evolved into a disruptive force in the vacation rental industry.

Whimstay’s origin story is one of entrepreneurial spirit and the willingness to take risks. As Alex recalls, “Me, Ben, and Jim sat down at a small table, opened a computer, and the inbox was at zero! We literally started from zero. I personally had a huge wave of fear wash over me, but then out of nowhere, a flash of inspiration just hit me—‘contact the North Lake Tahoe Chambers of Commerce.’” This pivotal moment led to their first listings and set the ball rolling for Whimstay’s growth.

The core idea behind Whimstay is simple but innovative. Unlike traditional platforms that list properties far in advance, Whimstay caters to travelers looking to book accommodations within 30 days or less. This approach complements, rather than competes with, larger platforms like Airbnb and VRBO. “We take care of travelers that are doing 30 days or less,” Alex explains, highlighting how Whimstay fills a crucial gap in the market.

Whimstay's strategy of building strong relationships with professional property managers has been key to its rapid expansion. By focusing on these partnerships, Whimstay has been able to scale quickly. As Alex puts it, “If you are a host, we work with professional property managements. They use software to distribute their properties. They have more properties that they manage, so it was worth it to make one call and get 100 listings instead of having an individual host.”

The company’s growth has been further accelerated by strategic agreements with industry leaders like Expedia Group and Booking.com. These partnerships have added an impressive 250,000 new listings to Whimstay’s platform. “We have a supply department, and that team is the one that brought us these great agreements and got the listings that we wanted,” says Alex. These collaborations are a testament to the value Whimstay brings to the travel marketplace.

Looking to the future, Whimstay has ambitious plans. While expanding their listings remains a priority, the company is also focused on perfecting its product. “Experience is always on the roadmap,” Alex notes, “but right now, we want to project what we are doing and really focus on the product and making sure the engineering is perfect. Our focus is to get one million bookings a day.”

Whimstay's journey from a fledgling startup to a significant player in the vacation rental industry is a story of innovation, resilience, and the drive to solve real-world problems. As the company continues to grow and evolve, it remains dedicated to offering a unique and valuable service to both property managers and last-minute travelers. With its eyes set firmly on the future, Whimstay is poised to continue redefining the landscape of short-term vacation rentals.