Vacation Rentals at Whimstay

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Whimstay is a relatively new player in the online vacation rental space, among the likes of Airbnb, Vrbo and others. Where Whimstay sets itself apart is in offering last-minute deals to travelers looking for a vacation home without planning ahead.


What Is Whimstay?

Launched in San Francisco in early 2019 by founders Ben Jamshahi, Alex Alioto and Kamesh Jasani, Whimstay is an online travel agency (OTA) that partners with property managers of vacation homes and condos to sell last-minute reservations for vacation rental properties.


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Whimstay builds partnerships with the property management companies that represent individual property owners. If a property isn't rented within three weeks of an open date, it is listed exclusively on and offered to last-minute travelers at a discounted rate.

What Whimstay Offers Property Owners

Last-minute vacation rentals may become available because the original person who booked them requested a cancellation or backed out late in the game. Now, the property owner has a rental available soon, and the property management company has a small window to find a new vacationer.


Enter Whimstay.

Through Whimstay, the property management company wins by having an avenue to rent out vacation properties that may have otherwise gone vacant. The property owner wins by boosting the visibility of their property and increasing occupancy rates.


On the news page of, the company regularly announces new partnerships, which means new properties added to the site.

What Whimstay Offers Travelers

Easy access to last-minute stays and spur-of-the-moment getaways is the first obvious advantage of Whimstay for travelers. Next, there are the exclusive deals that help your vacation fund go further. The price you pay and the price you could have paid are posted on each property listing.


All property listings have high-resolution photos, detailed descriptions of the unit and traveler reviews. Whimstay only works with professional property managers, so travelers can be assured that the rental properties are consistent with their listings and held to high standards.

The booking platform's search features are easy to use. Once you select a destination, you can filter by distance, features and amenities or house rules. If you're traveling with someone else, you can search together by activating the "Trip Chat" and collaborating on the plan. Planning a group trip to a national park? Set up Trip Chat and invite your fellow travelers to explore and discuss potential properties right on the Whimstay platform.


Because there is no individual property owner or host in the mix, Whimstay has instant booking. You don't have to wait for someone to agree to your reservation. Once you secure your stay with a credit card, the date is yours.

Be warned, though: because Whimstay's entire platform is based around date-sensitive properties, you may not change the date of your reservation once it is booked.


Whimstay Payment Options and Refunds

One of the new features of Whimstay that greatly enhances the user experience is the ability to split payments at checkout. If you are traveling with others and splitting the bill, you no longer have to work through a third-party banking app to chase down everyone's share. Instead, within 24 hours of the initial reservation, each traveler can log into and pay for their portion of the bill.


The refund policies are spelled out clearly on Whimstay's FAQ page. When booking, you may choose the 100-percent refundable option for an additional fee during checkout. If you choose the non-refundable option, the rental is final, and no refund will be issued. Review the booking app's full terms of service for complete details.


Travelers can use the online booking platform or download the iOS iPhone or Android Whimstay App.

Easy access to last-minute stays and spur-of-the-moment getaways is the first obvious advantage of Whimstay for travelers.


How Much Do You Save?

Whimstay's calculated savings are based on how much you would spend to stay in comparable, professionally managed accommodations in that same market during that same time period. The price you see on a property listing is the average nightly rate for that rental property for the next three weeks.

When you choose your dates and click "Book Now," you will see the specific rates, including taxes and any fees. Many property owners charge one-time fees for cleaning and other expenses related to your stay.

Overall, Whimstay prices tend to be 20 to 40 percent lower than market price and sometimes as much as 60 percent off, depending on the location, dates and property. That kind of savings on vacation lodging is one way to help your fun budget stretch a little further!