Your property setup wasn't right. Booking.com settings were off. By the end of the month, your occupancy tax is a mess. 😖 Serena V. ran into those exact errors in her own portfolio. That is why she built the fix. Having managed up to 50 rentals, Serena started Hostvisors to take on the compliance headaches operators deal with every month. They built an integration with Guesty that pulls every reservation and checks occupancy tax in real time. If a channel setting is wrong or taxes are undercollected, operators know immediately instead of waiting for a month-end surprise. Serena spoke with us about tightening regulations across the US, the UK, and Europe, and why catching errors early is the only way to stay compliant at scale. Hear her story below 👇

Management agreement, revenue share, or master lease? Get it wrong and you find out mid-contract, when occupancy dips. Victor Chen, Jeff Baars, and Dror Rasin put real numbers to all three. Simon Lehmann moderates. Free webinar, October 28, 2pm ET: guesty.com/event-lp/what-it-…

Changing your PMS during peak season is the one rule operators never break. When Cascadia Getaways knew they were about to grow rapidly, they did not wait. They made the switch to Guesty right in the middle of their busiest months. As an early team member at Vacasa, R. Gerard Lester, already had a clear standard for what large-scale operations need. What convinced him to make the move was seeing Guesty actively build out the capabilities his team needed, especially the tools essential for homeowners. From seeing the product roadmap up close to having hands-on support through a high-stakes migration, Guesty has been a terrific partner from day one. Hear why they made the move, and why finding the balance between AI and real human communication is the real priority for 2027. 🎥 Watch the interview with Jonah Mandel below 👇

Adding four major booking channels in 12 months usually breaks internal teams. The team get buried in sync errors, owners panic over calendar clashes, and operations spends the week firefighting instead of planning. For James Shaw, Chief Commercial Officer at Forge Holiday Group, expanding the Forest Holidays brand across Booking.com, Airbnb, Expedia, and Vrbo proved it does not have to be that way. The move delivered a huge uplift in bookings and revenue across the UK, Ireland, and New Zealand. But the back end stayed calm. The reason was not just the platform. It was the human alignment behind it. Daily and weekly check-ins with their dedicated Guesty account team kept every handoff tight, while GuestyPay handled the financial complexity so the team could focus on their guests and owners. As James explains, robust software gives you reach, but consistent team alignment makes that scale durable. Hear how James and the team built for global scale 👇

Tuesday, 9:21am. A three-star review lands: “The boiler barely worked.” 9:22am. Maintenance task opened. The repair window is blocked across every channel. Wednesday, 4:02pm. Job done. Task closed. Dates back on sale. And in the background, a weekly sweep catches two more blocks that were never lifted. Two forgotten weekends, flagged for cleanup. The boiler got fixed. Everything else? Already done. ⚡

Your listings have a new place to show up. 👀 Say hello to Stay Inc. , now connected to Guesty®. A vacation rental marketplace built for professional property managers, Stay gives travelers another way to discover your properties and get to know the business behind them. Connect directly with Stay 👉️ app.guesty.com/distribution/…

Growing a property portfolio changes the job of the person running it. Where do you learn that part? Simon Lehmann built the STR Academy to help property managers make the move from operator to CEO, drawing on more than 20 years of experience in the industry. We're proud to back it as the exclusive property management software partner, alongside Beyond, Pikl, and Breezeway. Built for operators managing 30 to 200 properties, the academy offers nine self-paced modules with practical tools to put the learning to work in your own business. Our community has plenty of ambition. Helping operators build the knowledge to match it is something we're glad to support. Explore the academy 👉️ simonlehmann.net/academy

Co-hosting or property management: which one actually builds wealth? Steve Schwab points out we build businesses to build wealth. That means the assets we invest in, like properties, and the value of the operations we run. In a co-hosting business, the contracts, the listings, and the assets belong to the owners. There's nothing to sell. 📄 With property management, you build contracts and accounts that go with the business 🔁 Put those contracts together properly and they can be assignable, depending on the state 📈 That's how you exit for real multiples So, as Steve puts it "why would you ever build a co-hosting business and then have to give it away for nothing when you're done?" This was a great battle live on stage between Steve and Bill Faeth at GuestyVal, hosted by Kate Cox. Check out the full Co-host vs Pro debate 👉️ youtu.be/8-ANUZL5VMM?si=kU0d…

Everyone's talking about what AI can do. But figuring out what it should actually do in your business? That's a different story. And no, you don't need to overhaul your entire operation to get started. Vered Raviv Schwarz, President & COO at Guesty, breaks it down into five steps: 🔍 𝗔𝘂𝗱𝗶𝘁. Forget job titles for a second. What does your team actually spend its day doing? 🧩 𝗗𝗲𝗰𝗼𝗻𝘀𝘁𝗿𝘂𝗰𝘁. Break those tasks into smaller skills and steps. You might be surprised how much goes into one seemingly simple task. ⚖️ 𝗖𝗹𝗮𝘀𝘀𝗶𝗳𝘆. What needs human judgment, empathy, or trust? And what's better handled by AI's speed, consistency, and scale? Some things need both. 🤝 𝗗𝗲𝘀𝗶𝗴𝗻 𝘁𝗵𝗲 𝗵𝗮𝗻𝗱𝗼𝗳𝗳. When work passes between AI and a person, who's responsible for what happens next? Don't leave that part to chance. 🧪 𝗣𝗶𝗹𝗼𝘁 𝗼𝗻𝗲 𝘀𝗸𝗶𝗹𝗹. Start small, see what works, and build from there. No need to reinvent everything overnight. The goal is to figure out whether humans or AI should own each part of the work, and make sure nothing falls through the cracks.

A very literal Sign of the Times. 🎟️ Harry Styles announces a New York residency. Tickets go on sale. Booking behaviour jumps 10X. Not on the concert dates. On the day people could finally make the plan real. Sally Henry of KeyData pulled up the spike at GuestyVal, and it’s a good reminder for operators: demand can move the second an event becomes bookable. So the question is less “what’s happening in my market?” and more: Where are guests going next, and what just gave them a reason to book? 🎥 Watch Sally's full data session from GuestyVal: youtu.be/AjS61NWv9tQ

“What do you actually want your day to look like?” Before automating more of the business, Landon Smith Founder and CEO of AirINN put that question to his team. They’d switched to Guesty because of the API, and used that flexibility to build around a few simple questions: 🤖 What can we automate? 🤔 What should we automate? 🧑 What do we want to keep human? That approach has helped them grow 5X with a team of three. Guesty gives them the product and API to keep building around the way they actually want to work. 🎥 Watch the full Guesty Live session from GuestyVal: youtu.be/hcQ92c4k4Po

You are never going to deliver the same quality with 500 properties as you did with 50. And you need to be okay with it. Dennis Goedheid ❤️ said it plainly on the Past 150 panel. When you were doing everything yourself, you knew: 🤝 The owner relationships 📈 The revenue management 🧹 What happened with the cleaning three weeks ago when that owner called At scale, some of that disappears. The job is to keep quality as high as possible, while being realistic about what changes. So what do you add back in? 📊 More sophisticated revenue management 🛠️ More services 💰 Better pricing 🏠 More value for the owner in different ways As moderator Brandy Canaley put it, sometimes a little healthy realism is useful. 🎥 Watch the full Past 150 panel from GuestyVal: youtu.be/QtCQHY5XMUs

A smaller building can sometimes be the smarter bet. Jeff Baars’ take on Master Leases: if you’re putting your own capital on the line, one of the best ways to de-risk the move is to start smaller. Ten, 15, maybe 20 units can teach you a lot about a market without betting the business on one huge building. HMAs shift the risk, but they don’t make it disappear. Your capital may be safer, but your brand is still on the line. And with a large asset, getting it badly wrong can hurt a lot more. 🎥 Watch the full urban STR panel with Simon Lehmann, Jeff, Dror Rasin and Victor C. from GuestyVal: youtu.be/OUSiqkEEQHk They discuss... 🏢 When Master Lease makes sense, and where it can go wrong 🤝 Why owner incentives matter so much in HMAs 📉 The ramp-up, rent increases and CapEx costs people underestimate 📍 Why knowing a market beats chasing scale for scale’s sake 🏷️ How brand matters differently with owners, corporates and guests 🧮 The advice for anyone underwriting an urban deal today

One set of property details. A bookable listing, guest guide and custom website out. Powered by the Guesty API. George Voutsis showed how Holihouse is taking the information they already collect about a property and using it to produce a lot more than a listing: 🏡 Bookable listings 📖 Guest guides 💻 Custom websites ⚙️ More of the setup work that used to be done by hand Once the property is understood, the same information can keep working across the business. 🎥 Watch the full Guesty Live: Under the Hood session with Simon Lehmann from GuestyVal: youtu.be/VhWjVk-z4Qs

Your bank account is about to get a lot closer to your PMS. Today, Guesty and Column are partnering to bring purpose-built banking to property managers. For eligible Guesty customers, that means deposit and trust accounts designed around how this industry actually handles money: owner funds, operating funds, permissions, approvals and all the complexity that comes with managing both. Guesty already knows the reservation, the owner, the payment and what should be happening in the books. Column knows what’s happening at the bank. And because both platforms are built on open APIs, those two sides can work much more closely together. 🔄 Automated bank reconciliation ⚡ Faster owner distributions 🏦 Banking built around the financial workflows property managers already run Guesty x Column 🤝 ordnl.link/wqKHR54

How often do you get a presentation that was clearly made entirely by Claude, and start wondering what the real thinking behind it was? Your guests and your owners will feel the same way. That was Jeremy Gall, founder and CEO of Breezeway, at GuestyVal. A year or two ago, automated replies felt like magic, to us and to our guests. Now everyone's used to it. Guests want predictability, owners want predictability, but repeat guests come from a relationship, and that takes the right balance between calculated optimisation and the human touch. 🤝 You won't be able to fool your owners 👥 And you won't be able to fool your team 🎥 Watch Jeremy's full session from GuestyVal: youtu.be/Dddo1NhXBY0

💡 They never post a photo of a property. Only the beach, the surf, and the food. This is the example James Varley founder and CEO of Host Planet, used at GuestyVal to explain what laser focus on your audience looks like: Beach Retreats in Cornwall sells the experience, not the house. His second story: a host who wanted corporate bookings from a refuse collection company put stickers on the bins. Go where your customers are, make the content they want. 🎯 Start. Then be laser focused on who you're speaking to. 🏄 Sell the experience, not the property. 📍 Go where your customers already are. 🎥 Watch the full Power of presence panel from GuestyVal: youtu.be/rTYTDwmMkBM

If you're a luxury VR operator: are travel advisors in your growth plan yet? 👀 Rachel Alday of Abode Luxury Rentals thinks they should be. The travel advisor world has grown fast, and in luxury vacation rentals, that shift is starting to have more sway. A few years ago, it wasn’t necessarily a channel operators were building around. Now? ✈️ Advisors are influencing where luxury guests go 🏡 Vacation rentals are a much bigger part of that conversation 🤝 And operators need to think about how they build those relationships If you’re serving the luxury guest, this is one channel worth watching closely. 🎥 Watch the full luxury panel with Rachel, Dawn Yeskulsky, Sarah Breitlander, and Kelly Ritch at GuestyVal: youtu.be/-fexkq4XVsc ✨ Why luxury is no longer just about the property 🤝 Working with travel advisors and reaching the luxury guest 🏡 When the wrong owner can make even the right property a bad fit 📆 Shorter booking windows, and how to manage owner expectations around them 🧘 The amenities luxury guests now expect, from wellness spaces to outdoor kitchens 📖 Why every property still needs its own story 🤖 Where AI helps in luxury hospitality, and where the panelists really don’t want it

How do you make an upsell something your guest is thankful for? That's the question Damian Sheridan put to Francois Gouelo 🔵 Gouelo, co-founder and CEO of Enso Connect 🔵, on the Revenue race panel at GuestyVal. Francois's answer starts with one question most operators never ask: why are you travelling here? His favourite example is an operator with 17 listings generating about $10,000 a month. He collects the usual details, then asks the travel reason, and treats an AI escalation as an opportunity rather than a problem. If the reason matches a package he can build, someone on the team curates it: romantic, birthday, wedding. That's about $5,000 to $6,000 a month from 17 listings❕️ ❌️ Not a store of options. ❌️ Not Ryanair-style forced steps. ✅️ Understand why the guest is coming, then curate. 🎥 Watch the full Revenue race panel with James Shaw and Jasper Ribbers from GuestyVal: youtu.be/OsGjm9w81sg

Where does the owner fit into revenue management? Right in the middle of it. Eduardo Botelho Miranda’s point at GuestyVal was simple: owners are one of the most important clients a property manager has. So if you lower the rate, change strategy, or a property is underperforming, the job isn’t finished when the change is made. You need to explain the why. That context can be just as valuable as the pricing decision itself. 🎥 Watch the full Guesty Live session with Simon Lehmann from GuestyVal: youtu.be/lhQrwZ7_i6c