Specialised Channel Manager for Whimstay

List and Manage Vacation Rentals Automatically on Whimstay

Whimstay is the leading vacation rental marketplace for travelers looking to book last-minute stays at a great value. Whimstay offers a best-in-class user experience via our app and website and provides hosts with top-notch support and an intuitive platform which makes filling unsold nights easy.


Benefits of connecting to Whimstay via Rentals United


Automatic Upload

Complete sync to add properties effortlessly


Automatic Update

Sync calendars, prices, photos & property info


Advanced Options

2-Way connection and more

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Service Features

  • Integration to multiple property management systems
  • A fraud check on cc before making a reservation
  • Exclusive last-minute deals
  • Whimstay is the merchant of record
  • Whimstay accepts multi-unit inventory
  • Whimstay works with instant Bookings
  • Your minimum stay will be synchronized

Key Info

Category Vacation rental site
Service Release Date 2018
Headquarter Location Wilmington, US
Minimum properties required 1
Website Visit now
Pricing model Commission based
Commission 3-5% from the rates received via Rentals United
What is synced Rates, Availability, Bookings, Photos and Property Info
Onboarding time 30 minutes - 1 hour
Minimum requirements No minimum requirement

How the Channel Manager for Whimstay works

  1. Signup via your Rentals United Dashboard.
  2. Whimstay will approve your request.
  3. Whimstay will set up a quick meeting to go over your listings.
  4. Whimstay will make sure your screening process is optimized for their website.
  5. Whimstay will publish your listings!

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.

Frequently Asked Questions

What sets Whimstay apart from other vacation rental platforms?

Whimstay focuses on last-minute vacation rental bookings. By specializing in the niche segment, the company complements rather than competes directly with industry giants and offers a dedicated channel for property managers to fill vacancies and generate incremental revenue.

How does Whimstay benefit property managers and hosts?

Whimstay provides property managers and hosts with a platform to book nights that would have otherwise gone unrented, often during periods of lower occupancy or shoulder seasons. The strategy generates incremental bookings, revenue, and profitability while offering better economics, more control over the customer experience, and reduced dependency on larger, more expensive channels.

What kind of travelers does Whimstay cater to?

Whimstay’s target audience is the spontaneous, experience-seeking Millennials and Gen Zs who prioritize unique adventures, local immersion, and flexibility.

How does Whimstay ensure a seamless booking experience for guests?

Whimstay has implemented advanced search capabilities, integrated dynamic pricing, loyalty programs, and a unique split payment feature allowing travelers to divide the cost of stay among multiple parties at checkout. Whimstay verifies travelers through partnerships with companies like SuperHog, ensuring property managers receive quality guests.

What is Whimstay’s growth strategy and plans?

With a recent $10 million equity financing round and a successful integration into Google Vacation Rentals, Whimstay is poised for rapid growth. The company plans to continue developing new products and features for enhancing the search experience, guest engagement, dynamic pricing, flexibility, loyalty programs, and ancillary financial products to generate more bookings for property managers during lower occupancy periods.