Short Term Rental Management

On this week’s episode of Short Term Rental Management, Luke sits down with David to unpack his journey from a full-time engineering career to owning six short-term rentals and managing more than 35 units for other investors. David shares how he leveraged disciplined investing, systems, and team building to scale, why pricing and operations matter more than hype, and what it really takes to leave a W-2 job for long-term freedom through real estate. The conversation dives deep into property management realities, software stacks, staffing, and why adaptability and honest pricing are essential in today’s STR market. How to connect with David: Website: https://shorttermconnections.com Direct booking brand: https://865vacations.com Instagram & TikTok: @865Vacations How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke explains how short-term rental success often depends on balancing two different mindsets: the creative right brain and the analytical left brain. He breaks down how creative operators excel at design, guest experience, and listings but often struggle with pricing and numbers, while analytical operators thrive on spreadsheets and projections but may overlook presentation and communication. Luke’s key takeaway is that understanding your natural strengths—and intentionally shoring up your weaknesses—is critical to running a profitable, sustainable STR business. How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke breaks down two recent SOP failures—when a deadbolt and backup lockbox both failed—and explains why that kind of catastrophic access breakdown is preventable with better systems. He shares practical fixes like replacing unreliable push-button lockboxes, tracking deadbolt install dates and lockbox details in a spreadsheet, and implementing a semiannual lockbox function test so you’re never scrambling during guest check-in. How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week's episode of Short Term Rental Management, Luke sits down with bookkeeper and real estate investor Ben Day of Lionshare Bookkeeping to demystify bookkeeping for short-term rental owners, from when you actually need a bookkeeper versus just a CPA to what clean books should look like. They dig into pricing for bookkeeping services, the difference between simple landlord books and complex trust accounting for property managers, and the tech stack Ben recommends—including tools like Tally Breeze, Get Clearing, Relay Financial, and QuickBooks Online to streamline STR finances and owner statements. How to connect with Ben: https://lionsharebookkeeping.com/ How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke digs into why you should always assume user error first when guests report that something is “broken,” using real-world examples like HVAC issues and TV/Roku remotes to show how basic property knowledge and calm troubleshooting can save you time, money, and stress. He also talks about why a quick phone call can turn a frustrated guest into a satisfied one, and how presenting yourself as a professional operation (even with just one property) helps you handle problems more smoothly. How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke dives into “The Word Yes” and how a simple mindset shift can dramatically improve your guest experience and reviews. Reflecting on the post-COVID era, Luke explains why hosts can no longer afford to say no to small requests like paper towels or detergent, and how embracing flexibility pays off in long-term success.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week's episode of Short Term Rental Management, Luke breaks down why he believes “repeat guests are for suckers” and why obsessing over getting people back to the same property is usually a poor use of time. He contrasts the heavy effort of building repeat-guest lists, direct booking systems, and loyalty-style incentives with simply leveraging platforms like Airbnb and Vrbo, which already spend massive amounts on marketing to bring in an endless stream of new guests. Along the way, Luke shares personal stories about travel habits, Disney trips, gas-price frugality, and mindset, all to drive home the point that your house isn’t that special, you’re a landlord first, and your energy is better spent finding new guests than clinging to the same ones.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke reflects on why nobody will ever care for your property quite like you do. Through stories from his own recent rehab project, he highlights the tension between perfectionism, delegating to contractors, and learning to let go when it comes to rental standards. The takeaway: focus on what matters most and don’t get bogged down by chasing flawless details.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke Carl hosts a Disney-market roundtable to compare on-property vs. off-property stays, demystify Disney Vacation Club, and spotlight resort-style STR communities near the parks where proximity and guest experience drive bookings. The panel shares practical playbooks on theming, pricing against Disney hotels, HOAs and amenities that meet Disney-level expectations, and current deal-making realities around Kissimmee/Orlando.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke unpacks three key money habits that can make or break your financial future. From everyday choices to long-term planning, he highlights simple but powerful shifts that can help hosts build lasting wealth instead of staying stuck in survival mode.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke explains what really happens when you sell an Airbnb or VRBO property. Drawing from his own recent sale, he walks through how Airbnb assigns a case manager to help rebook existing guests, while VRBO’s new policies now prohibit renting if the property is listed for sale unless strict conditions are met. Luke breaks down the challenges of transferring bookings, the risks if a buyer’s closing falls through, and why he believes sellers should keep things simple by providing buyers with a listing link and letting guests decide whether to rebook.    How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke recaps BiggerPockets Conference 2025 in Las Vegas—highlighting his and Avery’s sold-out STR bootcamp, a lively panel he participated in and why the city felt unusually packed and pricey. He shares quick takeaways on today’s demand and strategy—skip costly amenity overhauls and double down on service and operations—closing with a cautiously optimistic outlook for the STR market.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke explains why guests with eight to ten prior reviews often bring the most friction, while new guests with no reviews are usually fine, and reminds hosts that shoulder-season travelers have more options and can be pickier—so tighten systems and stay patient   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke shares why booking too far in advance (like next Summer) could be a costly mistake for hosts. He dives into how the market is shifting, what platforms are rewarding right now, and the timing strategies that can make or break your calendar performance. Tune in to hear how Luke approaches pricing and availability to stay ahead of the competition.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke breaks down his “Month Math” method—a no-nonsense approach to evaluating whether your nightly rates are realistic or simply driven by ego. He urges hosts to calculate what an entire month of bookings would gross and compare it to their monthly expenses. If your pricing implies a huge profit but you’re sitting vacant, it’s time to lower your rates. Luke emphasizes value, humility, and adapting to today’s market conditions.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week's episode of Short Term Rental Management, Luke breaks down recent jobs-report revisions, what they might mean for the Fed’s pending rate move, and how mortgage rates could wiggle in the short term even as the broader trend points down. He shares a strategic take on “sideline buyers,” why inventory may dip before bouncing back, and answers listener questions.     How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke shares a Disney/Universal trip debrief as a barometer for U.S. travel, noting lighter morning crowds, busier afternoons, and a stark contrast in customer service. He ties those observations to today’s market—rates likely easing, Main Street feeling pinched—and advises STR operators to prioritize competitive nightly pricing over splashy amenities, consider temporary cleaner-fee adjustments, and focus on delivering a clean, reliable guest experience.    How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke breaks down his strategy for maximizing bookings through the end of the year. He stresses the importance of having September and October at least 50% booked, holding October rates until September 8 before discounting, and treating early November and December as slow periods while enforcing five- to six-night minimums over Thanksgiving, Christmas, and New Year’s. Luke also shares why he believes travel demand will rebound as interest rates ease, why the idea of “market saturation” is meaningless, and how this season is the perfect time for deep cleans, maintenance, and refreshing your property photos with tasteful holiday decor.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

This week Luke is coming to you with a bonus episode he is calling Short Term Shop News! Luke breaks down Airbnb’s move to a single 15.5% host-only service fee starting October 27 and what it means for pricing, advising PMS users to raise Airbnb rates ~15.5% to keep payouts flat. Joined by Chuck Kramer and Avery Carl, the crew weighs consumer sentiment and competitive dynamics (VRBO’s lower take vs. potential price moves), plus cautions hosts to watch accounting on bookings straddling the change and consider “all-in pricing” as a short-term marketing edge.   How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode of Short Term Rental Management, Luke welcomes Tim Grillot back to the show—a real estate investor, car enthusiast, and now vacation rental photographer—who shares his journey from corporate life to STR ownership and creative entrepreneurship. They dive deep into the evolution of Airbnb photography, the technical side of staging and lighting, and how Tim and his wife are helping STR owners showcase their properties through immersive, guest-focused imagery. The episode also touches on vacation-town living, hospitality mindsets, and why answering your phone can set you apart.    Check out Scroll Stopper Photography: scrollstopperphotography.com    How to connect with Luke: The Short Term Shop - https://theshorttermshop.com/ Follow us on Instagram  Follow us on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon