Short Term Rental Management

On this week’s episode of Short Term Rental Management, Luke Carl sits down with Sam and Jay, the founders of HostBuddy AI, to break down how their property management journey led them to build an AI tool that automates guest communication. They share how scaling to 30–40 units exposed the nonstop demands of messaging, late-night guest issues, and operational burnout—ultimately pushing them to create a solution that handles 85–90% of guest communication automatically. The conversation dives into how AI can replace VAs, improve response times and reviews, personalize guest messaging, and help operators scale without sacrificing their time or sanity, while still emphasizing the importance of strong SOPs and human oversight. How to connect with Jay and Sam https://www.hostbuddy.ai/ @sam_mayes @jay_ullrich_ 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 discusses competition and the fear of “market saturation” in the short-term rental industry. He explains why competition is actually a positive sign that a market is working, encouraging hosts and entrepreneurs to focus on improving their service, amenities, and operations instead of worrying about other listings entering the market. Luke also shares broader entrepreneurial advice, emphasizing that success comes from maintaining integrity, working harder than competitors, and constantly refining your business to stand out. 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 talks with Annie, co-founder of HelloHost, about how her early Airbnb hosting experience led to building an AI platform designed to automate guest communications for short-term rental operators. Annie shares the story behind acquiring and renovating a 16-unit lakeside retreat in Canada, the operational challenges that inspired her company, and how AI can help property managers handle repetitive guest messaging while still maintaining strong guest experiences. The conversation also explores where automation fits in short-term rental operations and how hosts can balance technology with human service. How to connect with Annie: Email: [email protected] Website: https://hellohost.ai 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 breaks down a quiet but important policy change from Airbnb that now allows hosts in the United States to set a minimum age requirement for the booking guest up to 25 years old. He walks through the details of how the rule works, including disclosure requirements, ID verification limitations, and the fact that the age restriction only applies to the person making the booking, not the rest of the group. Luke also shares his perspective as a long-time operator, explaining why he personally plans to continue allowing 18+ bookings and why many hosts may be overestimating the risk of younger guests. 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 how hosts should think about spring break guests and why fear around parties is usually a sign of being new to short term rentals. He explains recent changes to Airbnb’s age limit policy, how to set clear expectations around age, noise, occupancy, and vehicles, and why most bad guests will reveal themselves upfront if you do your job properly. Luke shares real world examples of why spring break guests are often cleaner and more cautious than hosts expect, and why the real goal is not avoiding spring break, but renting the house responsibly. The episode reinforces the importance of strong rules, proactive messaging, and confidence in your systems so you are not micromanaging or panicking during one of the most profitable seasons of the year. 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 is joined by Steven Bolt to talk through the realities of building a short term rental property management company in the Poconos. Steven shares how he and his wife got started investing out of state, what they learned from their first STR experience, and how those lessons shaped their decision to manage homes for other owners. They discuss growing from a single property to managing more than a dozen units, the importance of professionalism, systems, and design in standing out in a crowded market, and the operational challenges that come with scaling responsibly. The conversation also touches on pricing tools, PMS changes, outsourcing revenue management, balancing growth with quality, and how Steven thinks about long term goals, family priorities, and building a sustainable business without losing what matters most. How to connect with Steven: https://www.poconolodging.co/ 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 kicks off a 2026 tips and tricks session covering everything from finding real estate deals in a shifting market to leveraging AI and optimizing pricing strategies. He and the team discuss why patience and persistence are key when making offers in today’s slower vacation markets, how tools like Host Buddy and PMS-integrated AI can dramatically reduce guest messaging time, and why VRBO payment terms and promotions can make or break your booking volume. The conversation also dives deep into PriceLabs seasonal profiles, competitor tracking, Booking.com promotions, and tactical ways to stay competitive as we head into spring. 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 is joined by Chuck for a rapid fire year end “clean out the computer” conversation covering a wide range of operational lessons and mindset shifts for hosts. They talk through managing guest expectations, why some guests arrive looking for problems, and how much of that behavior is created by hosts themselves through messaging and processes. The episode also covers practical systems like handling broken hot tubs, pricing decisively instead of making incremental changes, navigating the end of the new host boost, and knowing whether you actually want to rent your property or just keep it pristine. Along the way, Luke and Chuck emphasize biting your tongue with guests, letting go of emotional attachment to properties, being proactive with cash flow and cleaners, and focusing on systems that reduce stress while protecting reviews and long term performance. 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 is joined by Erica for an end of year recap focused on guest experience, pricing strategy, and operational improvements. They discuss how Airbnb’s changing amenities and interface updates can quietly impact listings and why it is important to regularly audit settings and messaging. Erica shares how reviewing guest feedback helps identify both strengths and recurring friction points, including how proactive communication can reduce common complaints before they happen. The conversation also covers year end pricing adjustments using PriceLabs, setting higher baselines for the new year, and how small but memorable amenities like Erica’s Nerf gun wall can help a property stand out while supporting repeat and direct bookings. 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 smaller, more affordable short-term rental homes are often easier to keep booked than large, high-dollar properties. He walks through the psychology of guest demand, noting that two and three bedroom homes tend to book faster because they fit more travelers’ budgets and search behavior, even when priced similarly to larger homes. Luke also ties this back to a long-term rental mindset, emphasizing that at the end of the day, it’s “just a house,” and steady, consistent demand often beats chasing premium amenities or oversized properties. 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 Airbnb’s new “date-specific cancellation policies” rollout, which lets hosts set different cancellation rules for different dates on the calendar (with the policy determined by the guest’s check in date). He walks through how the feature works and why it matters. Luke also briefly reviews Airbnb’s current cancellation policy options and notes this is Airbnb-only for now, with hopes it eventually becomes manageable through PMS tools via the API. 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 a candid and unfiltered story about getting fired by a long-term property management company—and the hard lessons that came with it. He walks through red flags like inexperienced managers, poor inspections, inflated rehab estimates, and conflicts of interest, while owning his own mistakes around communication under pressure. The episode serves as a real-world reminder of why vetting managers, setting expectations, and staying involved in asset oversight matter just as much as choosing the right 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 is joined by Libby of Co Host Oklahoma to unpack what it really takes to scale a co-hosting and property management business to 45+ units. They dive into balancing owner expectations with guest experience, navigating a high-profile $16,000 damage claim, and building scalable systems using tools like Hospitable, PriceLabs and custom automation. The conversation also explores branding, networking, co-hosting vs. property management, and why quality, simplicity, and strong relationships matter more than over-the-top amenities. How to connect with Libby: Website: https://cohostoklahoma.com Direct booking: https://hostlahoma.com Instagram & Facebook: @CoHostOklahoma 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 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