AI is becoming a practical advantage for vacation rental revenue teams. Property managers are working through shifting demand, owner expectations, pricing decisions, market data, and portfolio performance every day. The real challenge is turning all of that information into clear, confident action. In this clip from our first Revenue Reality…
Getting guests to your website is only half the job. The bigger question is whether your website gives them enough clarity and confidence to take action. In this episode, we sit down with Chris Walker, Owner of Luxury Homes of Hilton Head and CEO of Direct Booking Tools, to talk…
Many vacation rental operators are working to grow direct bookings, but the real opportunity is not just driving more traffic to their website. It is understanding what happens once guests get there. In this episode, we are joined by Chris Walker, Owner of Luxury Homes of Hilton Head and CEO…
AI is changing the way travelers search, and hospitality brands are having to rethink what visibility really means. In this clip, Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide, shares why traditional digital marketing is being disrupted by AI, from SEO and keyword search to the way…
Property management software is often seen as something operators adopt later, once the business is bigger or more established. In this clip, Pierre-Camille Hamana, founder and CEO of Hospitable, explains why the right tools should help operators get there sooner. For many smaller operators, the hesitation is understandable. Software can…
Loyalty is not built through one booking. It is built through every touchpoint that gives guests and owners a reason to stay connected. In this episode, we welcome back Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide, for a conversation on how one of the biggest names…
In this episode, we welcome back Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide. Mike shares what brought him back to the industry, what his new role looks like, and how Marriott Vacations Worldwide is approaching loyalty, customer experience, owner engagement, and long-term value. The conversation looks…
Revenue management comes with a lot of moving pieces. Events shift demand, acing changes quickly, owner questions need clear answers, and sometimes, getting to that answer means digging through more dashboards than anyone would like to admit. In this clip from our first Revenue Reality Check episode presented by Beyond,…
Why are so many vacation rental operators still managing without software? In this episode, Pierre-Camille Hamana, founder and CEO of Hospitable, shares why software adoption in the short-term rental industry still has a long way to go. Tools like CRMs, payroll systems, and accounting platforms are widely used by small…
Revenue strategy does not happen on autopilot. Markets shift, booking windows move, owners ask harder questions, and guests become more price sensitive. For vacation rental managers, the strategy that worked last month may need a second look today. That is the focus of Revenue Reality Check, a 6-part bimonthly series…
Does vacation rental software still have room to grow? In this episode, we’re joined by Pierre-Camille Hamana, founder and CEO of Hospitable, to talk about why many hosts and operators still hesitate to adopt property management software and how Hospitable is working to make these tools more accessible to operators…
In this episode, Alex & Annie sit down with Pierre-Camille Hamana, founder and CEO of Hospitable, to talk about the evolution of vacation rental software and why adoption across the industry still has so much room to grow. Pierre-Camille shares how his own experience as an Airbnb host in Brussels…
Pets? Always welcome. 🐾 Hot tubs? Proceed with caution. High-tech homes? Great, until someone needs a manual. Alex & Annie share their take on what enhances the guest experience and what might add more friction than value. Where do you land? Drop your take in the comments. #vacationrentals #shorttermrentals #strindustry…
STR Hot Takes, cold weather edition 🔥❄️ What makes a guest trust a host before they book? What should operators think about when designing a vacation rental? And what are travelers really anxious about when choosing a stay? Alex & Annie share their take on the small details that can…
Vrbo’s 2026 Vacation Rentals of the Year are out, and in this episode, Tim Rosolio shares what goes into selecting the homes that earn that recognition. Tim explains how the program highlights properties that consistently deliver a high-quality guest experience, whether they are run by an individual host or a…
What makes a vacation rental stand out? In this episode, we sit down (by the fire) with Tim Rosolio, Vice President of Vacation Rental Partnerships at Expedia Group, for a true fireside chat about Vrbo’s Vacation Rentals of the Year and the standards behind the recognition. Recorded at Lakefront Escape…
In this special episode, Alex & Annie sit down with Tim Rosolio, Vice President of Vacation Rental Partnerships at Vrbo, for a behind-the-scenes look at Vrbo’s Vacation Rentals of the Year program and what it takes to earn that recognition. Recorded on location at Lakefront Escape on Squam Lake, New…
In this episode, Amanda shares some of the horror stories Safely has seen across the short-term rental industry. Some are surprising, some are extreme, and some are genuinely difficult to hear. But they reflect a reality that operators know well. When something goes wrong at a property, the impact can…
In this episode, Amanda Martins of Safely explains why requiring at least ID screening is such an important step for operators. She shares that guest screening is not only useful for verification. It can also help deter certain guests the moment they see there is a process in place. While…
Not every guest stay ends with a five-star review. Some leave behind a mess. Some turn into a serious operational headache. And some become the kind of story you talk about for years. That’s exactly why we’re excited to launch Pour Decisions: When Stays Go Sideways, a new special series…
Have a story to share? We want to hear your worst guest stories. If you have a stay that went completely sideways and a lesson to go with it, submit it for a chance to be featured on a future episode of Pour Decisions. Bonus points if you bring your…
Growth is exciting, but not every new property is the right fit. In this episode, Jakob Dwyer, CEO of Awayday, shares why inventory selection plays such a critical role in long-term performance. Adding more homes may grow the portfolio, but adding the wrong ones can create operational strain, weaken brand…
In this episode, Jakob Dwyer, CEO of Awayday, shares why empowering local teams is essential to building a stronger vacation rental business. He explains why the people closest to the market are often the ones with the clearest view of what drives performance, from revenue opportunities and owner relationships to…
What does it take to grow a vacation rental company without losing the local identity that made it successful in the first place? In this episode, we’re joined by Jakob Dwyer, CEO of Awayday, to talk about how the company is scaling through local leadership, shared support, and strong operational…
