New Control Options for Hospitable Users Hospitable users can now disable all reviews in Settings > Hospitable Settings with a single toggle. This is especially helpful if you have hundreds of reviews and prefer to manually curate which ones display. What this means for you: Full control over your social proof. Highlight your best feedback without being overwhelmed by volume or outdated reviews.
The vacation rental industry has reached an inflection point. While platforms like Airbnb and Vrbo continue to dominate guest acquisition, savvy property managers are discovering that long-term success requires a more balanced approach—one that doesn’t leave your entire business vulnerable to algorithm changes or commission increases. Building a scalable direct booking strategy isn’t about abandoning online travel agencies (OTAs) overnight. It’s about creating a sustainable revenue model that gives you control, flexibility, and direct relationships with your guests. Start With the Foundation: Your Digital Presence The first step in any direct booking strategy vacation rental managers should implement is establishing a professional web presence that actually converts visitors into bookings. Your website isn’t just a digital brochure—it’s your most valuable marketing asset. Many property managers make the mistake of settling for generic PMS-provided templates that lack customization, load slowly on mobile devices, and fail to capture the unique character of their properties. These cookie-cutter solutions often convert at dismal rates because they weren’t designed with guest experience in mind. Instead, focus on creating a mobile-optimized booking experience that showcases your properties beautifully. More than half of your potential guests will visit from their phones, so if your site isn’t fast and intuitive on mobile, you’re losing bookings before the conversation even starts. Show Image The Guest Lifecycle Approach The most successful direct booking strategies treat guests as long-term relationships, not one-time transactions. This mindset shift fundamentally changes how you approach marketing. Consider the lifetime value of a guest who books directly. They might stay with you once this year, refer a friend who books twice, and return annually for the next five years. That single guest relationship could represent tens of thousands in revenue—far more valuable than the initial booking. To nurture these relationships, implement a systematic approach to guest communication: Email marketing remains one of the highest-ROI channels for vacation rental operators. Past guests already trust you and know the quality of your properties. A simple monthly newsletter keeping them engaged can drive significant repeat bookings. Leverage Your OTA Presence Strategically Here’s a truth many direct booking advocates don’t emphasize: OTAs can be powerful tools in your direct booking strategy vacation rental businesses use successfully. The key is to view them as guest-acquisition channels, not your entire distribution strategy. Think of OTAs as your marketing department. They spend billions attracting travelers and putting properties in front of potential guests. Your job is to deliver such an exceptional experience that those guests want to book directly next time. This requires a delicate balance. You can’t explicitly tell guests to “book direct next time” while they’re on an OTA platform—that violates terms of service. But you can create memorable experiences that naturally lead guests to search for you independently. Exceptional hospitality, thoughtful touches, and genuine connection make guests remember you. When guests do find you organically after an OTA stay, be ready with an incentive to book direct. This might be a 10% discount, a free night after multiple stays, early check-in flexibility, or personalized upgrades you can’t offer through OTA channels. Content Marketing That Actually Drives Bookings One of the most underutilized tactics in direct booking strategy vacation rental managers overlook is content marketing. Creating helpful, search-optimized content positions you as a local expert and captures guests in the research phase—well before they’re ready to book. Consider the search behavior of someone planning a trip to your area. They’re not immediately searching for “3-bedroom rental in [your city].” They’re asking questions like: By creating genuinely helpful content around these topics, you capture potential guests early in their planning journey. When they’re ready to book, your properties are top of mind because you’ve already provided value. This approach compounds over time. Each piece of content continues attracting potential guests long after you publish it. Unlike paid advertising that stops the moment you stop spending, and authority in your market. Measure What Matters The difference between property managers who succeed with direct bookings and those who struggle often comes down to measurement. You can’t improve what you don’t track. Essential metrics for your direct booking strategy vacation rental business should monitor: These metrics reveal where to focus your efforts. If your website traffic is strong but conversion is weak, you need to improve your booking experience. If conversion is solid but traffic is low, invest more in visibility—whether through SEO, paid advertising, or content marketing. Many property managers assume they need equal revenue from all channels. That’s not realistic or even desirable, especially when starting out. Set incremental goals: move from 5% direct bookings to 15%, then 25%. Each percentage point represents less dependency on third-party platforms and more revenue flowing directly to your business. Technology as Your Competitive Advantage The vacation rental landscape has changed dramatically. Technology that was once only accessible to large hotel chains is now available to independent operators. The property managers who thrive in the coming years will be those who leverage modern tools to deliver experiences that feel personal and professional simultaneously. Travelers increasingly prefer booking directly with properties when the experience is seamless and trustworthy. Your technology stack should eliminate friction at every step—from property search to availability checking to secure payment processing. The right platform integrates deeply with your property management system, automatically syncing availability and rates so you never have to worry about double bookings. It should provide fast-loading, mobile-optimized templates that actually convert visitors. And it should include the analytics you need to understand what’s working and what needs improvement. The Long Game Wins Building a successful direct booking strategy vacation rental operators can sustain takes time. It’s not about flipping a switch and instantly replacing all OTA revenue. It’s about systematically building assets—your website, your email list, your content library, your guest relationships—that compound in value. The property managers who succeed with direct bookings share a common trait: they think in years, not months. They understand that every guest relationship nurtured, every piece of helpful content published, and every website
“The goal is to automate the annoying so you can focus on the amazing.” In this episode, Gil sits down with Sean McGregor, founder of NoCodeSTR.com, to explore how vacation rental hosts can reclaim their time without sacrificing guest experience. Sean has hosted over 5,000 groups on Airbnb while maintaining a 4.98★ rating since 2018—all while traveling through 40+ countries with his family. What’s his secret? A powerful combination of no-code automation tools and AI that handle the repetitive tasks most hosts dread. From guest communication to review management, Sean shares exactly how he maintains a 100% five-star rating even during a 3.5-week road trip through the Balkans. If you’ve ever felt chained to your phone answering the same guest questions or wondered how to scale without burning out, this conversation will show you a better way. Sean breaks down the tools, mindset, and systems that let hosts run professional operations from anywhere in the world. Summary and Highlights 🎯 About Sean McGregor Sean McGregor is the founder of NoCodeSTR.com, where he teaches vacation rental hosts how to automate the tedious parts of their business using no-code tools like Zapier, Airtable, and AI. Since 2018, he’s maintained a remarkable 4.98★ rating on Airbnb while hosting more than 5,000 groups—proving that automation and exceptional guest experience aren’t mutually exclusive. What sets Sean apart is his 5★ Guarantee: he doesn’t take commission if a guest leaves anything less than a five-star review. This bold promise reflects his confidence in the systems he’s built, which handle everything from pre-arrival communications to post-checkout follow-ups. Sean’s approach isn’t theoretical. He’s built his business while working remotely from over 40 countries with his family, demonstrating that proper automation creates true location independence. His free 5-day course at NoCodeSTR.com has helped hundreds of hosts discover what’s possible when they stop doing everything manually. 🔑 Key Highlights: Building a Five-Star Business on Autopilot The “Automate the Annoying” Philosophy Sean’s entire approach centers on one principle: identify the repetitive, time-consuming tasks that drain your energy and automate them. For most hosts, this means the same guest questions, check-in instructions, and review requests that repeat with every booking. “The goal is to automate the annoying so you can focus on the amazing,” Sean explains. This isn’t about cutting corners—it’s about redirecting your limited time toward high-impact activities like improving your property, building relationships with direct booking guests, or actually enjoying the lifestyle that drew you to hosting in the first place. The mindset shift happens when hosts realize that guests don’t care how they get information—they just want it quickly and accurately. Whether an answer comes from you personally or a well-designed automation makes no difference to guest satisfaction. No-Code Tools That Cost Nothing Per Listing One of the biggest misconceptions Sean addresses is that powerful automation requires expensive software or technical expertise. The tools he relies on—Zapier, Airtable, and Make—can be implemented at zero cost per listing for most hosts. These platforms connect your existing systems (PMS, email, calendar) and create workflows that run automatically. For example, when a new booking comes in, an automation can instantly send personalized welcome messages, add the guest to your communication sequence, and update your team’s task list—all without you lifting a finger. Sean emphasizes that the learning curve isn’t as steep as most hosts imagine. “If you can set up an Airbnb listing, you can build these automations,” he notes. The key is starting with one annoying task and building from there, rather than trying to automate everything at once. For hosts focused on growing their direct booking channel, these same no-code tools integrate beautifully with website forms and inquiry systems, creating a seamless guest experience from first contact through checkout. AI as Your 24/7 Guest Experience Manager The real game-changer in Sean’s systems is how he’s integrated AI—not as a replacement for genuine hospitality, but as an enhancement. His AI-powered tools handle routine questions, provide instant responses outside business hours, and even anticipate guest needs based on patterns in previous conversations. During his recent Balkans road trip, Sean’s automations and AI systems maintained a 100% five-star rating without any human intervention. Guests received immediate answers to questions about WiFi passwords, local recommendations, or check-in procedures—all delivered in a natural, helpful tone that reflected his brand. “The technology has reached a point where guests genuinely can’t tell they’re interacting with automation,” Sean shares. But he’s quick to clarify that AI works best when it’s trained on your voice, your property’s unique features, and your approach to hospitality. This is particularly powerful for hosts managing multiple properties or building a portfolio. Instead of multiplying your workload as you scale, properly implemented AI and automation mean your systems scale without requiring proportional increases in your time. The Five-Star Guarantee: Confidence Through Systems Perhaps the most striking aspect of Sean’s business model is his willingness to offer a 5★ Guarantee—he only collects commission when guests leave five-star reviews. This isn’t just a marketing gimmick; it’s a direct result of the confidence he has in his automated systems. “When you’ve systematized every touchpoint in the guest journey, you know exactly what experience they’re getting,” Sean explains. His automations ensure consistent communication timing, complete pre-arrival information, and timely follow-up after checkout—all the factors that influence whether a guest leaves a glowing review. This approach also creates a virtuous cycle: because Sean’s systems are designed to generate five-star experiences, he attracts clients who are serious about quality and willing to invest in proper automation. The guarantee becomes a filter that aligns everyone’s incentives toward excellence. For hosts considering professional website implementations or upgrading their booking systems, this principle applies equally: when your infrastructure is solid, you can make bold promises about the experience you deliver. Location Independence Without Compromise Sean’s lifestyle proves that automation isn’t just about saving time—it’s about creating genuine freedom. He’s worked from 40+ countries with his family while maintaining his 4.98★ rating, demonstrating that the right systems let you run a professional operation
“As long as you’re providing value, hopefully your marketing will be mostly perceived generously and people will want to receive it.” What if the key to competing with major OTAs wasn’t just about building a better website—but capturing data from every single guest who stays at your property? Arthur Colker, Founder & CEO of StayFi, discovered this truth while helping a New Orleans property manager escape 99% OTA dependency. In this episode, he shares how a WiFi-based data capture solution evolved into a full guest marketing platform powering direct bookings across vacation rentals, boutique hotels, and hospitality brands. Arthur reveals why guest data ownership is the biggest missed opportunity in short-term rentals, how diversifying channels matters more than eliminating OTAs entirely, and the groundbreaking StayFinder meta-search tool launching soon that will let travelers compare direct booking prices against major platforms. Whether you’re managing 2 properties or 200, Arthur’s insights on guest data strategy and the evolving hospitality tech landscape will reshape how you think about building an independent brand. Summary and Highlights 🎯 Meet Arthur Colker Arthur Colker is the Founder and CEO of StayFi, a guest marketing platform that started as a WiFi data collection tool and evolved into a comprehensive solution for vacation rentals, boutique hotels, and independent hospitality brands. Since 2018, Arthur has been helping property managers capture guest data and build independent booking channels that reduce reliance on major OTAs. Before StayFi, Arthur worked as a marketing consultant across various industries. His entry into short-term rentals happened almost accidentally when he took on a vacation rental operator as a client and discovered they had zero guest data despite managing 200 properties. That gap became the genesis of StayFi—a platform now used by thousands of operators who understand that guest data ownership is the foundation of a resilient, profitable hospitality business. Arthur is passionate about helping independent operators compete with major platforms, not by undercutting them, but by building their own brands and creating direct relationships with guests. His latest project, StayFinder, aims to make direct booking discovery as easy as booking through an OTA—while delivering real savings to travelers. 💡 Key Takeaways ✅ Guest data is the most overlooked asset in short-term rentals — Most operators collect names and emails only from bookers, missing everyone else in the reservation✅ Direct booking isn’t about replacing OTAs — It’s about channel diversification and building a resilient business that isn’t dependent on one platform✅ Marketing works when it delivers value — Position direct booking as a “secret” that saves guests money, not just a way to avoid fees✅ Your property needs to rank on Google — If someone searches your listing name and can’t find your direct site on page one, you’re losing bookings✅ Unique property names matter for SEO — Generic names like “Cozy Creek Cabin” make it nearly impossible to rank and be discovered✅ Founders need conviction, not just optimism — Arthur calls it “delusional self-belief,” but you also need to listen when customers tell you what’s not working🏠 How StayFi Started: Solving One Client’s Problem Arthur didn’t set out to build a hospitality tech company. He was doing marketing consulting for various businesses when he landed a short-term rental operator called Heirloom, managing around 200 properties across New Orleans, Boston, and Scottsdale. Their goal was simple: build a brand identity and figure out how to get guests to book directly. The challenge? They were 99% dependent on Airbnb for bookings and had zero guest data. No names, no emails, no phone numbers. Arthur realized that acquiring new guests is expensive and trust-dependent. The easiest path to direct bookings would be marketing to people who already stayed and loved the properties. But how do you market to ghosts? He looked for existing solutions—captive portal systems used in cafes, airports, and hotels. Nothing worked well for single-family vacation rentals. So he built a custom solution using white-labeled hardware and a basic splash page that collected marketing consent when guests logged into WiFi. V1 of StayFi was scrappy. No customer portal. No self-service. Arthur manually configured everything for each client. But it worked. And when he looked around the industry, he realized the problem was universal. That’s how StayFi was born. 📈 The Evolution: From WiFi to Full Guest Marketing Platform The early years were a grind. Through 2019, StayFi was still a part-time project. Then Arthur went full-time—right as the hardware partner got acquired and pricing became unfeasible. He had to rebuild the tech stack while simultaneously dealing with COVID shutting down his 10-15 paying customers overnight. But instead of folding, Arthur used the downtime to build StayFi’s first self-service portal and flash page builder. By the time short-term rentals roared back in 2021, the platform was ready to scale. Timing couldn’t have been better—hosts were angry at Airbnb for how they were treated during the pandemic, and the industry was hungry for tools that reduced OTA dependence. Fast forward to today, and StayFi has evolved far beyond WiFi data collection. The platform now includes: 🔹 Homepage Tool — A link-tree-style page for guests that consolidates all the resources they need during their stay🔹 Email Marketing Software — Purpose-built for vacation rentals, not generic tools like MailChimp🔹 PMS Integrations — Pulling data from property management systems to create a unified guest database🔹 Upsell Amplification — Helping operators present offers like early checkout, mid-stay cleans, and local experiences to all guests, not just bookers The guiding principle? Collect guest data from every touchpoint, then help operators monetize that data—whether through rebookings, upsells, or entirely new revenue streams. For property managers who also run real estate businesses, tour companies, or retail shops, StayFi has become a powerful cross-marketing engine. Guests who stay in vacation rentals are often the same people who later buy properties in that market. The data becomes invaluable. 🔍 StayFinder: The Next Frontier in Direct Booking Discovery Arthur’s newest project, StayFinder, tackles a different problem: guest discovery. Most direct booking tools focus on converting existing traffic
Now Live for All Users Your property pages now display correct meta information when shared via Facebook and other social networks—no more broken previews or missing images. Why this matters: First impressions happen before guests even click. Clean, professional social previews increase click-through rates and build trust from the very first interaction.
Here’s the question that trips up most new vacation rental hosts: “Should I build a direct booking website right away, or wait until I’m more established?” The answer might surprise you: Build it on day one. Use it on day 365. I know what you’re thinking. Why invest in a direct booking site when 90% of your bookings will come from Airbnb for the next 12-24 months anyway? Isn’t that wasted money? Not if you understand what successful hosts know: your direct booking site isn’t about immediate bookings—it’s about building infrastructure while OTAs do the heavy lifting 🏗️. The Email That Changes Everything 📧 Picture this: It’s month 14 of your vacation rental journey. A guest who stayed with you six months ago sends you a message: “Hey! We loved your cabin. Planning to come back next month. Can we book directly with you instead of going through Airbnb? We’d love to save on those fees.” Now you have two choices: Option A: You scramble. You don’t have a website. You manually check your calendar across multiple platforms. You send them a payment link through Venmo or Zelle. You write up a rental agreement in Google Docs. It takes you 3 hours, feels unprofessional, and the guest gets nervous about whether this is legitimate. Option B: You reply with: “Absolutely! Here’s our website: [yourpropertyname].com – you can see real-time availability and book instantly. Thanks for being a returning guest! 🎉” See the difference? Option B took you 30 seconds. Option A cost you time, credibility, and possibly the booking. The infrastructure-first strategy means you’re ready when opportunity knocks 🚪. Year One: OTAs Are Your Marketing Engine (And That’s Perfect) 🚀 Let’s be clear about something: if you’re launching your first vacation rental, Airbnb and VRBO should absolutely be your primary booking channels for Year 1. Why? Because they’re providing something you can’t buy: instant distribution to millions of travelers actively searching for places to stay. Without these platforms, it would take years to build enough organic traffic to sustain your mortgage. They handle the marketing, the trust-building, the payment processing, the review system—all the infrastructure that makes guests comfortable booking with a stranger. But here’s the strategic play most hosts miss: while OTAs are filling your calendar, you’re building the foundation for independence. Every guest who books through Airbnb isn’t just revenue. They’re: You’re not competing with OTAs in Year 1—you’re using them to build your direct booking engine for Year 2 and beyond. The Math That Sells the Day One Strategy 🔢 Here’s why having your direct booking site ready from day one makes financial sense: Scenario 1: No Website (Most Hosts) Scenario 2: Infrastructure-First (Smart Hosts) The difference? The second host captured 2-3x more direct bookings because the infrastructure was ready when guests wanted to use it 💰. The Email Multiplier Nobody Talks About 📬 Most hosts think email collection means getting one email per booking. That’s leaving money on the table. Tools like Stayfii capture emails from every person who connects to your WiFi—not just the person who booked. If you have a property that sleeps 10 people, you’re potentially collecting 8-10 emails per stay. Let’s do the math on Year 1: By the end of Year 1, you could have a database of several hundred qualified leads who’ve already experienced your property. But here’s the key: you need somewhere to send them 🎯. Your direct booking website isn’t just a place to book—it’s the hub of your entire marketing ecosystem: Without it, you’re collecting emails with nowhere to send people. Why PMS Websites Don’t Cut It (Even Though They’re Free) 🚫 Almost every property management system offers a “free” direct booking website. So why not just use that? Because there’s a massive difference between a booking checkout page and a marketing website. PMS websites are designed for one scenario: a guest who already knows you and trusts you needs a place to complete a transaction. They work great for that. But they don’t: Think of PMS sites like a cash register—functional but not compelling. You need a storefront that actually sells. The E-Commerce Playbook That Changed Everything 🛒 Here’s an unfair advantage most vacation rental hosts don’t know about: the e-commerce industry already solved this problem a decade ago. Think about the parallels: In e-commerce, no serious seller relies 100% on Amazon anymore. They use Amazon to build awareness and collect customers, then convert them to their Shopify store for higher margins and customer data. Sound familiar? 🤔 The tools that e-commerce pros use work just as well for vacation rentals: Want to learn advanced marketing tactics? Don’t search “vacation rental marketing”—search “Shopify email marketing” or “how to run Facebook ads for e-commerce.” You’ll find thousands of free, detailed tutorials that translate perfectly to vacation rentals. The Three-Year Timeline (But Start Today) ⏱️ Let’s set honest expectations. Here’s what the realistic timeline looks like: Year 1: Foundation Phase Year 2: Activation Phase Year 3-4: Momentum Phase Notice what’s different here? Your website is built in Year 1, but it’s actively working for you across all three years 📈. The hosts who wait until Year 2 to build their site? They’re always playing catch-up. The hosts who build on day one? They’re ready to capture demand the moment it appears. The Pool Cabin Lesson: Buy for the Numbers, Market with the Brand 🏊♂️ Here’s a story that illustrates the power of having your infrastructure ready: One host bought their first cabin—a four-bedroom property in a valley. No mountain views, nothing Instagram-worthy. It performed okay but wasn’t a home run. For a year, they obsessed over optimization instead of scaling. Their second property? A pool cabin with a massive basement converted entirely to an indoor pool with a 100-inch theater system. This property became their star performer, generating more revenue at lower operating costs. But here’s the key: both properties were marketed through the same direct booking website. When guests loved the first cabin, the website showcased
We’ve refined the details that make your site feel truly yours. From how your properties appear when shared on social media to giving you more control over reviews and introducing new ways to organize your portfolio—these updates put the finishing touches in your hands. What this means for you: Your brand shows up consistently across every channel. Whether a guest discovers you through Facebook or browses collections on your site, you control the narrative and presentation.
Technology is transforming short-term rentals—but are we losing the heart of hospitality in the process? In this episode, Jessica Gillingham, CEO of Abode Worldwide and author of “Tech-Enabled Hospitality,” challenges the notion that automation and personalization can’t coexist. As a strategic advisor to transformative technology companies across the global hospitality sector and host of the Pillow Talk Sessions podcast, Jessica brings a unique perspective on building category leaders. From revealing why 90% of hosts only use 30-40% of their PMS capabilities to explaining how Netflix-style personalization could revolutionize guest experiences, Jessica shares insights from interviewing over 30 industry leaders. Whether you’re managing one property or a hundred, you’ll discover why the future of hospitality isn’t about choosing between technology and human connection—it’s about using one to amplify the other. Summary and Highlights 👤 Meet Jessica Jessica Gillingham is the CEO of Abode Worldwide, a strategic public relations agency specializing in elevating the profile of transformative technology solutions across the global hospitality, lodging, and living sectors. Abode sits at the heart of the developing intersection between work, life, and play in real estate and hospitality, partnering with brands playing a lead role in this transformation. A regular industry speaker, author, and adviser, Jessica is also the host of the Pillow Talk Sessions podcast and author of “Tech-Enabled Hospitality” (Kogan Page, August 2024). Drawing on interviews with over 30 industry leaders, her book examines how technology is transforming every aspect of hospitality operations and the guest experience. She’s also the creator of the Abode Worldwide Short-Term Rental Index, now in its third edition, which catalogs over 200 tech companies and trends shaping the STR industry. 🎯 Why This Episode Matters Most property managers are sitting on goldmines of untapped potential. Jessica reveals a startling reality: operators typically use only 30-40% of their existing technology’s capabilities. This isn’t just about underutilization—it’s about missing the fundamental shift happening in hospitality. While other industries, such as e-commerce, have seamlessly integrated digital experiences into every touchpoint, vacation rentals remain “clunky” and fragmented. This episode cuts through the noise of endless tech solutions to address the real question: How do you leverage technology without sacrificing the warmth and personalization that defines true hospitality? Jessica’s perspective, informed by years working with both hotel and vacation rental technology companies, offers a rare bird’s-eye view of where the industry is heading and what operators need to do now to stay competitive. 💡 The Mindset Shift: Investment vs. Cost One of the most powerful insights Jessica shares is the divide she observed while researching her book: successful operators view their tech stack as an investment that enhances their business, while struggling operators view it as a necessary expense. This mindset difference determines everything—from which tools you adopt to how you implement them. Operators who treat technology as an investment actively seek to understand its full capabilities, integrate systems to create seamless experiences, and continuously optimize their digital guest journey. Those who see it as a cost often implement the bare minimum, leaving powerful features dormant. The gap isn’t just philosophical. As Jessica points out, guests now expect the same frictionless digital experiences they get from booking doctor appointments, ordering food, or shopping online. Everything in our lives has been digitalized—except, often, the hospitality booking journey. <a href=”https://craftedstays.co/blog/”>Property managers who fail to bridge this gap</a> risk being left behind as the industry consolidates and guest expectations continue rising. 🔍 The Education Gap: Why Hosts Aren’t Using Their Tools Jessica identifies a critical problem plaguing the industry: operators often lack awareness of their own knowledge gaps. Most hosts and property managers can’t identify where automation could help them because they haven’t clearly defined their operational gaps. Even more challenging, they don’t fully understand what their existing software can do. This creates a vicious cycle. Without understanding your problems, you can’t evaluate solutions effectively. Without understanding your solutions, you can’t leverage them to solve problems. Jessica compares this to any software we use—”We’re on Riverside right now,” she tells Gil, “I bet you don’t use the whole caboodle of what Riverside can do for you.” The solution? Strategic education. Before adding another tool to your stack, invest time in understanding what you already have. Map your operational pain points. Then systematically explore whether your current PMS, guest communication platform, or pricing tool already addresses those challenges. As Jessica emphasizes throughout the conversation, <a href=”https://craftedstays.co/blog/”>the most successful direct booking strategies</a> start with understanding your foundation before building upward. 🏨 The Accidental Entrepreneur Problem Jessica makes a crucial distinction that many hosts overlook: “Most hosts are accidental hosts. You don’t go to university thinking I’m going to be a professional property manager.” This creates unique challenges because running a short-term rental business requires three distinct skill sets that rarely come naturally together: Hospitality expertise – Understanding guest needs, creating memorable experiences, and maintaining service standards Business acumen – Managing finances, hiring teams, scaling operations, and strategic planning Real estate knowledge – Property selection, market analysis, and investment strategy Unlike long-term rentals or commercial real estate, which have established frameworks and educational pathways, vacation rental operators often stumble into the business without realizing they’ve started a 24/7 hospitality operation. As Jessica notes, “It’s always on. Property managers tend to be extremely hardworking, putting in a lot of hours into their businesses.” The path forward involves recognizing these gaps and actively seeking education. Whether through podcasts like Booked Solid, industry conferences, or peer mastermind groups, successful operators treat learning as a core business function rather than an occasional activity. 🤝 Technology + Hospitality: Not an Either/Or Perhaps the most important theme Jessica emphasizes is captured in a single quote from Ryan Killeen, CEO of The Annex in Toronto: “The future of hospitality is hospitality.” Despite all the discussions about AI, automation, and efficiency, the winners in this space will be those who use technology to enable hospitality, not replace it. “Hospitality doesn’t always have to be in person,” Jessica explains. “It can be delivered through digital methods. It’s
Most vacation rental operators treat guest acquisition like a transaction. They optimize their listings, adjust their pricing algorithms, and wait for platforms to deliver bookings. But there’s a fundamental flaw in this approach: you’re building someone else’s business, not your own. 🏠 The reality is that successful direct booking strategies don’t start with marketing tactics—they start with a mindset shift. When you view your vacation rental as a standalone brand rather than an inventory item on a marketplace, everything changes. Your focus moves from competing on price to competing on experience, from one-time guests to lifetime relationships. ✨ The Long Game of Direct Bookings 🎯 Many operators expect immediate results from direct booking efforts. They launch a website, run a few ads, and wonder why the bookings aren’t flooding in. This expectation reveals a misunderstanding of how brand loyalty actually develops. Direct booking success operates on a different timeline than OTA performance. While platforms can deliver immediate visibility through their established traffic, building your own booking channel requires patience and consistency. The first nine months typically focus on relationship building and brand establishment. Real momentum comes when those guests return for their second, third, and fourth stays—all booked directly with you. 📈 Properties that achieve 70-80% direct booking rates don’t get there through shortcuts. They get there through sustained effort over multiple years, treating each guest interaction as an investment in future revenue. Marketing Begins Before the Stay 🎬 The guest journey doesn’t start at check-in. It starts the moment someone books with you, and how you handle that crucial period determines whether they’ll remember you when planning their next trip. Consider what happens psychologically after someone makes a large purchase: buyer’s remorse sets in. They’ve committed significant money to your property, and now they’re second-guessing that decision. Your job is to eliminate that doubt immediately. 💭 A simple personalized video message sent within hours of booking can transform that anxiety into excitement. The message doesn’t need to be polished or professional—authenticity matters more than production value. Acknowledging the guest by name and reassuring them that you’ll take excellent care of them addresses their concerns directly. Following up with a physical touch point, like a refrigerator magnet with your property branding, keeps your property top-of-mind during the weeks or months before their arrival. Every time they pass their refrigerator, they’re reminded of their upcoming vacation. When friends visit and ask about the magnet, your guest becomes your marketer. 🧲 The Power of Strategic Simplification 🎨 Attempting to personalize every aspect of the guest experience sounds appealing, but inconsistency kills brand building. Trying different welcome gifts, varying your communication style, or changing your amenities based on guest preferences creates operational chaos and dilutes your brand identity. Successful operators identify signature elements that can be replicated consistently at scale. Whether it’s a specific food item, a welcome ritual, or a communication cadence, consistency builds recognition and expectation. Guests come to associate that specific experience with your brand. 🍪 This doesn’t mean eliminating personalization entirely—it means creating systems that allow personalization within a consistent framework. Your core offering remains the same, but you can adapt around the edges based on guest needs. Extracting Actionable Guest Feedback 💬 Most operators rely solely on post-stay reviews for feedback, missing critical opportunities to understand guest needs and prevent problems. Strategic feedback collection happens at multiple touchpoints throughout the guest journey. Pre-arrival surveys serve dual purposes: they help you prepare for specific guest needs and they demonstrate attentiveness. Asking where guests found you provides attribution data for your marketing efforts. Asking about their vacation goals allows you to proactively share relevant local information. Offering to answer property-specific questions creates an opening for personal connection. 📋 In-property comment cards capture real-time feedback while guests can still remember details. This feedback often prevents negative reviews by giving guests a private channel to share concerns you can address. Asking about their best memory provides positive content for future marketing. Post-stay communication reinforces the relationship and opens the door for referrals—but only after you’ve demonstrated the quality of your product. Requesting referrals before someone has experienced your property puts the cart before the horse. ✉️ Content Creators as Strategic Marketing Partners 📱 Working with social media content creators represents a form of advertising, not free promotion. Approaching these partnerships with clear business objectives prevents wasted effort and disappointing returns. The critical factor is audience alignment. A content creator with 50,000 followers provides no value if their audience doesn’t match your ideal guest profile. Geographic location, family composition, income level, and travel preferences all matter when evaluating potential partnerships. Finding the right creators requires actual research. Geographic-specific searches on Instagram combined with demographic filters help identify creators whose audiences overlap with your target market. Traditional Google searches can surface local media coverage of content creators in your area. 🔍 When launching new properties or features, content creators can generate immediate awareness and social proof. A single weekend stay can produce content that reaches hundreds of thousands of potential guests, filling your calendar faster than organic growth alone. The Competitive Advantage of Being Small 🏆 Larger property management companies often view scale as an inherent advantage. More properties mean more revenue opportunities and operational efficiencies. But scale also creates constraints that smaller operators can exploit. Personalized guest communication becomes mathematically impossible at 50+ properties. Writing individual welcome videos, sending handwritten notes, and making personal phone calls simply doesn’t scale. This creates an opening for smaller operators to compete on relationship depth rather than portfolio breadth. Review data consistently shows that smaller operators maintain higher guest satisfaction scores. The reason isn’t mysterious: they can deliver authentic, personalized service that guests recognize and value. In an increasingly automated world, human connection stands out. 🤝 Owning Your Business Model 💼 Every vacation rental operator makes a fundamental choice: build your business on rented land (OTA platforms) or build your own foundation. Platforms provide convenience and immediate access to millions of travelers. But that convenience comes
Review Sync Improvements for Hostaway & Hospitable Users We’re enhancing how guest reviews sync to your CraftedStays site. Reviews now pull automatically, and we’re actively working on editing capabilities so you can curate which reviews display most prominently. Coming soon: Full review management tools to help you showcase your best guest feedback and build even stronger social proof.
