Last Minute Vacation Rental Site Whimstay Gaining Traction

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Whimstay is the leading last minute vacation rental marketplace focused on providing exclusive discounts. Whether travelers want a deal, are on a budget, or are simply feeling spontaneous, Whimstay offers up to 60% off last minute getaways to prime destinations, and also offers huge savings anytime in the off-seasons across the U.S., Mexico, and Canada.

Whimstay is more than just another channel partner to the property managers and owners it serves. The company has established a first-mover advantage filling vacancies exclusively for the vacation rental segment (homes and condos), in addition to providing a more user-friendly alternative compared to the larger travel OTAs and travel marketplaces, resulting in incremental guests, more bookings, higher occupancy rates, increased revenue per home or condo, and increased profitability, all while maintaining its partners’ branding as much as possible.

Whimstay has grown exponentially over the past two years, integrating into most of the vacation rental software companies, contracting with hundreds of property management companies, increasing the number of properties listed on its site by over 300%, and achieving over 120,000 user downloads of its mobile app.

Whimstay is capitalizing on an $80 billion global market opportunity with the benefits of vacation rentals vs hotels well-documented. Over 50% of short-term rental properties go unrented each night, resulting in billions of dollars in revenue lost each year. In addition to booking last minute stays as well as increasing occupancy rates and RevPAR in the off-seasons, which the company is benefitting from as we transition to more normal seasonality and post-2021 rush back to travel, Whimstay is also benefitting from newer growth trends such as increasing remote work, and younger travelers now being twice as likely to book a vacation rental vs. a hotel.

Key Players

Ben Jamshahi, co-founder and CEO of Whimstay, has always been passionate about innovation and entrepreneurship, especially in consumer-based businesses. Ben grew up traveling and became introduced to the vacation rental industry early in his career. He conceived of the idea for Whimstay in 2018. Whimstay was founded to create a win-win outcome for travelers and property managers. Ben has owned numerous vacation rental properties over the past 20 years and understands the benefits of the sharing economy firsthand. Ben loves to surf, travel, and spend time with his three children outside work.

Whimstay’s newest team member, Chief Operating Officer David Weiss, has spent the past ten years helping OTAs, travel marketplaces, and payments companies scale operations, negotiate and manage partnerships, develop products that enhance end-to-end customer experience, and execute growth strategies including implementing global payment solutions. Prior to that, David spent 25 years advising companies, boards, private equity, and venture capital firms on a broad range of operating initiatives, M&A, and financing transactions across the following sectors: Travel & Hospitality, FinTech, PropTech, Sustainability, Diversified Technology, and Industrials.

Whimstay Technology Highlights

Whimstay uses unique data science and insights from its highly targeted audience and other proprietary sources to offer tailored search and pricing solutions for its travelers and the most efficient last minute booking channel to its property manager customers. Whimstay believes its customers deserve to find precisely what they are looking for, expect to be offered personalized recommendations, and rest assured that their payments and data are secure.

The last minute vacation rental marketplace, Whimstay, believes booking a last minute vacation should be easy and fun, and should not put any traveler under pressure nor create anxiety for guests searching for a great experience. The company designed its app with those objectives in mind, and with unique features and functionalities which enable travelers to search for listings on the go easily. It’s relatively early days for Whimstay, but the company sees its app becoming more popular, and believes it will be one of the apps commonly used by travelers as part of their daily routine.

Whimstay is continuously improving its differentiated end-to-end last minute vacation rental solutions by launching a more traveler-friendly search and booking experience, providing far better pricing than a traveler can get on another channel, generating more bookings by increasing conversions, as well as enhancing traveler communications with Whimstay and with our property manager partners. In addition, the company is extremely excited by a series of data science initiatives that will enhance everything it does across functions, is expanding into Europe, and lastly, will be introducing new features and functionality to make guests and its partners more secure from a risk management and safety standpoint.


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David Weiss is the Chief Operating Officer of Whimstay. Prior to Whimstay, David served as President at a travel and real estate payments business, growing the company from $70m to over $200m in revenue during his tenure. David also launched an advisory business focused on Travel & Hospitality, FinTech, and PropTech, serving marketplaces, OTA’s, SaaS businesses, private equity, and venture capital firms across a range of initiatives including payments strategy, partnerships, product development, scaling operations, go-to-market strategies, M&A, and financing.