Why I Stopped Trusting Airbnb Alone for Last-Minute Bookings (and did THIS) | Alex Alioto

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0:00 – Introduction & The Last-Minute Booking Strategy
0:14 – Meet Alex Alioto & The Whimstay Story
0:43 – Understanding Gen Z and Millennial Travelers
1:00 – Jason’s Hosting Background & Market Trends
2:18 – Why Whimstay? Filling the Last-Minute Gap
6:00 – Booking Windows & Demographic Shifts
12:01 – Comparing VRBO, Airbnb, and Whimstay Customers
14:08 – How Whimstay Pricing and Discounts Work
19:09 – Extending the Shoulder Season & Off-Season Bookings
21:09 – Integration, Operations, and Avoiding Double Bookings
24:43 – Adapting to New Travel Behaviors
28:54 – Payment Processing & Merchant of Record
29:29 – Expanding Whimstay’s Reach in the Northeast
30:42 – Closing Thoughts & Guest Plugs


Can Last-Minute Bookings Actually Boost Your STR Revenue?


Last-minute bookings aren’t just a backup plan anymore—they’re becoming a key revenue strategy for short-term rental hosts. In this episode, we sit down with Alex Alioto, co-founder of Whimstay, about how shifting traveler behavior—especially among Gen Z and millennials—is reshaping the way hosts think about occupancy, pricing, and calendar gaps.


Alex shares how Whimstay helps property owners capture value from expiring inventory, extend the shoulder season, and stay ahead of modern travel trends. The conversation dives into how hosts can adapt their strategies to meet rising demand for flexibility, while still delivering standout guest experiences.


Whether you’re a seasoned host or just exploring the STR space, this episode offers fresh insight into the future of vacation rental booking behavior—and how to make it work in your favor.


Things we discussed in this episode:


The strategy and benefits of filling last-minute gaps in vacation rental calendars.


How Gen Z and millennial travelers are driving the trend toward shorter booking windows.


The founding story and unique value proposition of Whimstay as a last-minute rental marketplace.


The importance of a diverse distribution strategy for property owners.


Differences in traveler behavior and expectations across generations.


The impact of remote work on travel patterns and booking flexibility.


Operational challenges, such as integration with property management systems and avoiding double bookings.


Pricing strategies, including last-minute discounts and dynamic pricing tools.


The potential to extend the shoulder season and increase off-season bookings.


The role of guest experience and local touches in attracting modern travelers.


Get in touch with Alex:


Instagram - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/whimstay/⁠
LinkedIn - ⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/company/18786646/admin/dashboard/⁠
Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.whimstay.com/ ⁠


#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals
#VacationRentals #LastMinuteBookings #TravelTrends
#Whimstay #GenZTravel #MillennialTravel #PropertyManagement #DynamicPricing #GuestExperience


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