Recently, I covered vacation rental platforms to keep an eye on in 2026.
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My top contenders are Airbnb, Booking, VRBO, Vacasa, and Houfy. However, there’s a new (private rental) sheriff in town that you should know about.
Welcome to Whimstay, a platform that offers last-minute savings on short-term vacation rentals from popular sites like Airbnb and VRBO. The marketplace-style setup lets you connect with hosts who need to fill in the rental gaps on their calendars.
You can book stays on Whimstay across North America, the Caribbean, and even Europe. Whimstay even locked in a partnership with Wyndham Destinations, letting you save on select hotel bookings through its vacation clubs, resorts, and timeshares, too.
By working directly with property owners, you can save between 10-60% on rates. (The average is around 25%.) I also love that Whimstay as real customer support agents ready to speak with you any day of the week, helping you hammer out any problems.
You can get started by searching for your destination and dates—but what else do you need to know about how to use Whimstay to your fullest advantage?
Alex Alioto, co-founder of Whimstay, let me dig into the details during a recent interview.
How to use Whimstay to save on private rentals like Airbnb
The best rates are within 30 days of check-in
Whimstay works by connecting you to property managers and hosts who want to fill their rental calendars. That means the best deals are the last-minute. Alioto points out that the best rates are for rentals within 30 days of your check-in date—but you can also find even cheaper, more last-minute deals, if you’re really bargain-hunting.
Off-peak days (Sunday-Thursday) offer the steepest savings
Because more travelers build their trips around weekends, you can find even better Whismtay deals during the week. Sunday through Thursday, according to Alioto, are the peak days for savings. In general, mid-week offers have the highest discounts. (Flights and car rentals are also often cheaper during weekdays.)
The Split It feature makes group bookings a breeze
Whimstay has a unique Split It feature that lets you divvy up the private rental rate based on the total number of guests. That’s a handy feature for large groups—especially if no one wants to volunteer their credit card for the full payment. Instead of the hassle of figuring out how much each person owes and to whom, the Split It feature automatically splits the bill for you.
Couples can search for properties by amenities like hot tubs & fireplaces
Groups, couples, and solo travelers can use Whimstay to find their ideal rental. Just select how many guests you are, and the types of rental amenities you need. For couples, Whimstay makes it easy to find an effortlessly romantic property. Just search for amenities like hot tubs, fireplaces, water views, and more—just like you would on Airbnb or VRBO.
No need to wait for special deals or promos
Usually, travel deals and discounts are organized around seasonal holidays—but Whimstay lets you shop around for deals year-round. Once again, you can find savings up to 60% on private rentals within a 30-day period or less. No need to wait for price drop alerts. Shop when you’re ready to plan your next adventure—no matter the time of year.
Alioto says these destinations are taking off on Whimstay…
I asked Alioto which destinations in the United States are ‘heating up’ on Whimstay. Here’s what he shared:
- City bookings in Chicago, New York, Boston, and Seattle are trending
- Beach destinations like Destin, Myrtle Beach, Gulf Shores, and San Diego regularly list some of Whimstay’s lowest rates
- Cabin bookings in mountainous areas like Denver, Broken Bow, and Gatlinburg are also popular with travelers
