Field Notes

Demand is softer than it was at our recent high point, 2022. Supply has grown. Booking windows are compressing. If you've been watching your calendar this spring and feeling the urge to drop your rates — I understand the instinct. But that instinct is costing you more than a slow week. It's the most expensive habit in STR management, and it tends to run quietly in the background until you look at the numbers and wonder where the year went. The panic discount is a learned resp

I want to be careful here, because this is not an argument against dynamic pricing tools. PriceLabs, Wheelhouse, Beyond — these are good tools. I use them with my clients every day. They do many things no human brain can do at speed and scale. But there's a belief that's become so widespread in this industry that it's almost invisible now: the belief that activating a dynamic pricing tool is the same thing as having a revenue strategy. It isn't. And the gap between those two

So full disclosure. I'm not a soccer follower. But even I know that the 2026 FIFA World Cup is the largest sporting event in the world. It's being hosted across sixteen cities in the United States, Canada, and Mexico — with the US hosting the majority of matches across cities including New York, Los Angeles, Dallas, San Francisco, Seattle, Miami, and Philadelphia. So kind of a big deal in the hospitality world. The demand tailwind this creates for short-term rentals in those

The tools are getting smarter. But the operators who understand what the tools can’t do will have the edge. The conversation around AI in the STR industry has moved fast. A year ago, the question was whether operators should use AI tools. Today, the question is which ones and how. According to Buildium’s 2026 Industry Report, the number of property management companies using AI tools tripled in a single year — jumping from 20% to 58%. The operators who aren’t using these tool

Tighter rules are reshaping the STR landscape. The operators who understand this will have an advantage. If it feels like the regulatory environment around short-term rentals has gotten more complicated in the last twelve months, that’s because it has. The rate of STR regulation changes positive and negative are starting to gain speed. Cities and states across the country are moving quickly, and the changes are not uniform. Some markets are tightening. Some are loosening. And

When the world shifts, the data shifts with it. Here’s what operators need to know. If you’ve been watching the news, you already know the Middle East is in the middle of a significant conflict. What you might not have had time to consider is what it means for the STR industry — and specifically, what it means for operators who are paying attention to where demand moves when a major travel region suddenly becomes unreachable. The short answer: a lot is shifting; shifting dema

New data from the FY2025 earnings reports for both Airbnb and Booking highlights an interesting trend in the vacation rental industry: let's look at the numbers of Booking.com vs. Airbnb Booking.com is closing the gap with Airbnb faster than many people expected. In fact, Booking.com 's alternative accommodations segment now books about 84% as many nights as Airbnb , despite having less than half the number of vacation rental listings . That raises an important question for

If you follow short-term rental forums or marketing advice online, you’ve probably noticed a lot of conversation lately about new approaches to writing listing descriptions . Airbnb listing copy is changing. Many of the suggestions focus on making listings feel more emotional, experiential, and lifestyle-driven rather than purely functional. Examples include: experience-focused headlines storytelling descriptions highlighting unique amenities hyper-local recommendations using

Airbnb released its Q4 and full-year 2025 financial results, and while the headlines talk about strong growth, the real implications for hosts are more nuanced.

Why This Matters Travelers increasingly expect flexibility and lower upfront barriers before committing to travel. Reserve Now, Pay Later reduces friction for guests who: Don’t want to pay upfront Are coordinating travel with others Are balancing cash flow or timing Are comparing multiple options This means that booking decisions may occur earlier in the planning process, with less financial commitment required right away. What Airbnb Reserve Now, Pay Later Means for Hosts (

My take on AirDNA's 2026 Hottest Markets Report

Here's the problem they solve: flexible cancellation policies drive more bookings—but they also expose you to major revenue loss when guests cancel at the last minute. “You should switch to a flexible cancellation policy,” they said. Meanwhile, the forecast shows rain at the mountain… and your inbox starts filling with cancellations. Roam gives you income protection that lets you offer flexible cancellations  without  eating the cost when guests back out. You get reimbursed e