545. The New Rules of Buying Short-Term Rentals in 2026

The short-term rental market is shifting—and what worked even a few years ago won’t cut it anymore.In this episode, we sit down with Kenny Bedwell to break down the new rules of buying short-term rentals in 2026. From changing demand patterns to increased competition and rising guest expectations, we’re unpacking what’s actually happening in the market—and how to adapt.Kenny shares how he’s still finding profitable deals across the country, why average properties are falling behind, and what it takes to create a top-performing listing today.They get into:Where STR investors should be looking right nowWhy drive-to markets are outperformingThe biggest mistake people make when analyzing dealsHow to identify the right guest and design for themWhat separates top 10% properties from the restHow the industry is evolving and what to expect nextIf you’re thinking about buying—or trying to stay competitive—this episode will help you rethink your strategy and move forward with clarity.

Are you lowering your nightly rates because your calendar looks empty? If so, you might be panic pricing and leaving money on the table.In this episode of Thanks for Visiting, Sarah and Annette break down one of the most overlooked metrics in short-term rental pricing strategy: your booking window.Your booking window tells you when guests actually start shopping and booking their stay. If you don’t understand this data, you may be discounting too early, waiting too long to adjust pricing, or reacting emotionally instead of strategically.The hosts share the two biggest pricing mistakes they see hosts make, how to identify your booking window, and a simple framework to divide your calendar into zones so you can make better pricing decisions.If you’ve ever stared at an empty calendar and felt tempted to slash your prices, this episode will help you replace panic with data and turn your calendar into a revenue tool.Remember: there is cash in your calendar, you just need the right strategy to mine it.

If you’re hosting in 2026, chances are you’ve asked yourself at least one of these questions:Am I underpriced if my calendar is filling faster than everyone else’s?Should I switch to midterm rentals during the slow season?Why is my listing cheaper than the competition but still not getting booked?In this episode, Sarah and Annette break down three real questions from hosts inside the Priced and Profitable Bootcamp VIP coaching sessions—questions that many hosts are quietly struggling with right now.They unpack what these questions reveal about pricing strategy, market positioning, listing trust, and the mindset shifts required to actually build a profitable short-term rental business.You’ll learn why being the most booked property isn’t always a win, how slow seasons should really be approached, and why lowering your price can actually hurt your bookings instead of helping them.If you’re serious about optimizing your STR business in today’s market, this episode will help you ask better questions—and make better decisions.

If your cleaner controls your calendar… this episode is for you.Today, we’re breaking down how to actually hire a five-star cleaner (not reactively, not desperately, and definitely not based on price alone).Because here’s the truth: You are not hiring a cleaner. You are hiring the guardian of your five-star brand.In this episode, we walk you through:The four hiring questions you must answer before posting a jobHow to turn operational pain into a magnetic job descriptionWhere to actually find professional short-term rental cleanersThe exact interview questions that reveal mindset, not just skillRed flags to watch for (even if they “clean beautifully”)How to incentivize and retain A-player cleaning partnersYour turnover team is the backbone of your business. If you get this right, everything else becomes easier.If you get it wrong? Chaos. Let’s fix it.

If you feel like you’re working harder than ever but not seeing the profit you want from your short-term rental, this episode is for you.Today, we’re breaking down the pricing mistakes we still see hosts making every single day and how those mistakes are quietly costing you thousands in missed revenue.We cover:Why seven-day pickup is the most underused pricing lever in your businessWhy your base rate is not “set it and forget it”Why relying only on Airbnb is putting your revenue at riskAnd the real reason pricing guilt is holding you backHere’s the truth: you are not “just an Airbnb host.” You are a business owner. And numbers are neutral.If you want more bookings, better guests, and a more profitable year, it starts with understanding your data and pricing with confidence.Stop under-earning. Stop guessing. Start charging what your market is already willing to pay.

The 2026 FIFA World Cup is coming to the United States, and for short-term rental hosts, this is not just another busy weekend.It is a multi-week, multi-city revenue opportunity.In this episode, we break down what is really happening behind the headlines, including those $17,000 Airbnb listings near MetLife Stadium, and what smart hosts are doing differently.This is not about price gouging. It is about understanding demand timing, fan behavior, booking windows, and strategic positioning.Whether you are in a host city, a drive-to market, or nowhere near a stadium, the strategies in this episode apply to any major event in your area, from concerts to conventions to college football.We cover:Why pricing only the final weekend is a massive mistakeHow to map match schedules and identify demand wavesTiered pricing versus one emotional rateWhy you should never be the first one sold outHow to optimize your listing for group logisticsThe operational blind spots that can crush your reviewsThe World Cup is a historic opportunity, but only if you approach it strategically.

Where you host matters, but how you operate matters even more.In this episode of Thanks for Visiting, Sarah and Annette break down what it really means to host legally and responsibly in today’s short-term rental landscape. From host-friendly states to high-risk markets, they explain why relying on outdated advice, spreadsheets, or assumptions can cost you everything.You’ll learn how state and city regulations differ, why Airbnb won’t protect you from illegal operations, and how professional hosts stay informed, compliant, and profitable long-term. This episode is a must-listen for anyone buying, operating, or scaling a short-term rental business.Resources mentioned:Thanks for Visiting Bootcamp: Join the waitlist!Mentioned in this episode:Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.

If the idea of hiring a virtual assistant feels overwhelming, or like something only “big hosts” do, this episode will change how you think about leverage.In this episode, we break down five practical ways short-term rental hosts can use virtual assistants to improve follow-through, stay organized, and grow their business without handing over the keys or losing visibility.Virtual assistants aren’t about stepping away from your business, they’re about staying focused on what actually matters. We share real-world examples, common mistakes hosts make when hiring VAs, and how to build a partnership that creates momentum instead of chaos.If you’re juggling too many tasks, dropping balls, or stuck doing work you know shouldn’t be on your plate anymore, this episode will show you where to start.In this episode, we cover:Why virtual assistants are a lever, not a luxuryThe daily, weekly, and monthly tasks VAs should ownHow VAs can support guest communication and salesUsing VAs to improve operational follow-throughHow VAs can help you stay accountable to your goalsWhy most VA relationships fail and how to avoid itResources mentioned: Thanks for Visiting Bootcamp: Join the waitlist!Mentioned in this episode:Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.

Many hosts say “I feel like my listing is buried.” But feelings don’t get bookings—data does.In this episode, we break down the four Airbnb metrics that actually impact bookings and show you how to use Airbnb’s Professional Hosting Tools to pinpoint exactly where guests are dropping off in your funnel.Instead of randomly tweaking photos, prices, or descriptions and hoping for the best, you’ll learn how to make one strategic change at a time, guided by real performance data, not guesswork.We also reveal a common mistake hosts make that quietly hurts bookings, even when they feel like they’re doing everything right.If you’re ready to stop reacting and start hosting strategically, this episode will show you where to look and what to fix.In this episode, we cover:Why Airbnb data is more reliable than host “gut feelings”How the guest booking funnel actually worksThe four metrics every host should be trackingWhat causes guests to stop clicking — or stop bookingHow to test changes without tanking your performanceThe mindset shift that separates reactive hosts from strategic onesResources mentioned: Check out the Thanks for Visiting YouTube ChannelMentioned in this episode:Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.

What if your short-term rental could make money without guests sleeping there?In this episode, Sarah and Annette break down unconventional — but proven — ways hosts are generating additional revenue by leveraging their properties during the day, shoulder seasons, or slower periods.From commercial photo shoots to coworking days, private events, pool rentals, and wellness experiences, this conversation challenges the idea that overnight stays are the only path to profitability.You’ll learn:How hosts are monetizing their properties without overnight guestsWhy commercial photography and content creation can be highly profitableHow day-use bookings attract entrepreneurs, teams, and creatorsWhere private events can make sense — and where they don’tWhy pools, outdoor spaces, and amenities can become revenue driversThe guardrails you must have in place before exploring these ideasThese strategies aren’t shortcuts — they require planning, boundaries, and intention. But for the right properties and markets, they can unlock meaningful new income streams.Resources mentioned:Thanks for Visiting Bootcamp: Join the waitlist!Mentioned in this episode:Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.Working hard but not making the money you should? Join us for our live Priced & Profitable Bootcamp.