Whimstay

Whimstay is a company that specializes in offering discounted last-minute vacation rentals across the US, Canada, and Mexico by aggregating unsold vacation rental properties. The company offers a webpage and mobile app catering to travelers that book their trips within the last three weeks before their departure. Whimstay works with property managers to fill their vacancies during off-seasons, shoulder seasons, and other booking windows that usually have lower occupancy rates and RevPAR. The company negotiates exclusive discounts with property management partners, offering travelers up to 60% discounts for last-minute stays. Bookable property types include cabins, lodges, apartments, and condos. Rental properties offered include amenities such as accessibility options, household appliances, climate control, indoor fireplaces, fully equipped kitchens, parking facilities, fitness centers, hot tubs, swimming pools, workspaces with Wi-Fi, and flexible house rules allowing pets, events, smoking, and children. Rental prices range from ~USD 1,500 to USD 54,000 per month, with the company guaranteeing up to USD 1.3 million for accidental damages to property managers and guests. Whimstay also provides two tools: TripChat and Split It. TripChat enables travelers to chat with friends and family directly from the Whimstay app or website. It allows users to share properties, react to messages, and collaborate on planning a group trip without leaving the platform. The Split It feature enables travelers to split the total payment for their trip among multiple individuals. Users can invite fellow travelers during the checkout process to split payment and confirm the reservation by paying their share.

Whimstay generates revenue by charging a 5%–10% traveler service fee and a 3%–5% host fee based on the rental price.

In Mach 2024, Whimstay added over 30,000 resort rentals to its platform

Key customers and partnerships

The company is the exclusive last-minute distribution partner in North America to property management companies Vacasa and Turnkey and also provides travel insurance via its partnership with Generali Global Assistance. As of April 2023, Whimstay received over 100,000 customer downloads of its app and has partnered with over 680 property management companies to list last-minute stays. In February 2023, the company partnered with Google to integrate Whimstay’s 150,000 rental properties into Google Travel’s search function.