Specialised Channel Manager for Whimstay

The Birth of an Idea

The seeds of Whimstay were sown in 2017 when founder David Weiss noticed a recurring problem with his vacation rental properties. Despite being located in prime destinations like Hawaii and Lake Tahoe, Weiss’ properties were experiencing low occupancy rates, often hovering around 50%. Unsatisfied with his property manager’s explanations, Weiss embarked on a six-month journey to find an overstock model platform that could help him fill those vacant nights.

Much to Weiss’ surprise, no such platform existed. Undeterred, Weiss rallied a team of like-minded individuals, including Alex Alioto and Jim Rossiter, and in late 2018, Whimstay was born. The company’s mission was to generate incremental bookings, revenue, and profitability for property managers by focusing on last-minute vacation rental bookings.

A Complementary Approach

Whimstay’s strategy has been to complement rather than compete directly with industry giants. By specializing in last-minute deals, the company serves a distinct segment of travelers with unique needs.

Whimstay’s model provides incremental revenue for property managers and hosts by capitalizing on expiring inventory. The complementary channel fills a gap left by other platforms, offering peace of mind that the entire distribution strategy is covered.

Catering to the Spontaneous Traveler

The Millennial and Gen Z demographics seek multiple micro-vacations per year, preferring unique adventures and destinations like a historic farm stay in the Shenandoah Valley or a modern home tucked into the high desert of Joshua Tree.

Studies show that younger travelers prioritize experiences over traditional life milestones like buying a home or starting a family. Millennials and Gen Zs crave authenticity and local cultures, which short-term rentals provide. Unlike a conventional hotel room, a rental allows travelers to live like locals, adding depth to the overall travel experience.

Whimstay’s value proposition taps into the need for spontaneity, value, and flexibility. By offering last-minute deals, the company enables spontaneous adventures while providing significant savings on vacation rentals across North America.

Embracing Authenticity and Adaptability

Whimstay’s strengths are adapting and responding to market changes with agility. The company recognizes that nimbleness and responsiveness are keys to success.

Going beyond just business strategies, Whimstay’s approach is about being genuine in the platform’s mission and approach.

Weiss says that the platform’s alignment is the result of understanding its audience deeply and crafting a business model that aligns with their values and needs.

Collaborative Partnerships for Mutual Growth

Whimstay’s commitment to complementing rather than competing has led to strategic partnerships with industry leaders. One notable example is the company’s recent collaboration with Wyndham Destinations, one of the largest destination brands in the world.

Along with several other premiere resort brands, collaborative efforts have allowed Whimstay to add over 30,000 resort listings, some of which cannot be found on any other major platform. The mutually beneficial relationship expands Whimstay’s inventory and provides property managers and owners with a dedicated channel for last-minute bookings.

Robust Technology and Customer-Centric Features

Underpinning Whimstay’s success is a proprietary marketing engine and a suite of innovative product features designed to enhance the user experience. From advanced search capabilities to integrated dynamic pricing and loyalty programs, the company’s technology is geared toward generating more bookings for property managers during periods of lower occupancy.

Whimstay’s commitment to customer-centricity is further exemplified by integrating with Google Vacation Rentals. The company has implemented a unique split payment feature, too, allowing travelers to divide the cost of stay among multiple parties at checkout and eliminating the need for third-party payment splitting apps.

A Promising Future

Whimstay has a recent $10 million equity financing round and a 7-fold increase in year-to-date bookings compared to the previous year. Weiss attributes Whimstay’s success to the resilience and caliber of his team, the differentiated product offering, and the quality of partner and customer relationships.

Plus, with a $60 billion market opportunity for last-minute vacation rentals, the company is set to create a win-win scenario for travelers and property managers.