Short Term Rental Management

Fresh back from the Vacation Rental Management Association (VRMA) conference in Nashville, Luke recaps his first time attending the industry’s biggest property management event, now in its 41st year. His biggest takeaway is that every booth was built around AI and tech, and if you aren’t leaning in, you’re getting left behind. He shares practical ways he’s using AI in daily life, from a new AI calendar app to Spotify’s Discover Weekly to connecting Strava to Claude ahead of his marathon.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

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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

The Short Term Shop team shares a wide-ranging 2027 outlook for short-term rental investors. They discuss the buyer’s market in vacation destinations, interest rates and financing strategies, rental performance expectations, changing booking platform fees and policies, and the growing role of AI in guest operations and property research. CPA guests Matt and Amanda explain depreciation and the short-term rental tax strategy, including material participation and carrying unused losses forward. Agent Natalie offers guidance on using AI during the buying process: use it to research and organize information, while building understanding through conversations with local professionals. The team also reviews software developments in guest messaging, cleaning coordination, pricing, and property amenities, and closes with advice on keeping accurate, real-time records of time spent working on a rental.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

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Join theShort Term Shop Facebook group

Check out theShort 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

Luke shares his firsthand experience following a direct-hit Category 3 hurricane in the Destin and 30A area, discussing the realities of storm damage, the importance of inspecting and removing dead trees before disaster strikes, and why property managers should prioritize safety over profits when it comes to guest cancellations and refunds. He also reflects on the risks of owning beach properties, the costs of insurance and maintenance, and the resilience of coastal communities after a storm. His biggest takeaway for landlords and property managers: inspect your trees, plan ahead, and always put people’s safety first.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

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Join theShort Term Shop Facebook group

Check out theShort 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

Luke tackles one of the most common questions he gets: how do you find a plumber, roofer, or other vendor for your short-term rental? He explains that finding them is only half the battle, since tracking people down, following up repeatedly, and holding them accountable is a huge part of being a property manager. Then he does a live screen share showing how he uses AI to build a vendor list, from writing detailed prompts about location, recent recommendations, and review counts to refining results until he gets names and phone numbers. He also shares what he looks for in a vendor, like small operations that welcome rental work, and what to ask when you call, from availability to whether they can really show up when they say they will.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke explains how he’s using Vrbo ad campaigns to boost listing visibility, including how he’s offsetting advertising costs with guest fees, and shares why he ultimately decided to integrate Vrbo directly with Hospitable despite initial concerns about the new technology. Luke also breaks down the benefits he’s seeing from managing Vrbo listings directly through Hospitable, including improved customer support and a more streamlined workflow.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke shares how he’s using AI integrations and Chrome extensions to streamline property management. He covers practical applications like analyzing potential properties, managing VRBO ad campaigns, updating listing headlines, adjusting PriceLabs settings, monitoring property issues, and handling guest communications. He also discusses where AI still falls short—particularly with revenue and pricing data—and why hosts need to treat AI more like an employee that requires training, oversight, and clear instructions.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl gets candid about what guests are actually looking for when they book a short-term rental and why owners need to understand the experience they're selling. He explains how kitchens, privacy, space, and amenities can give STRs an advantage over hotels, while also emphasizing the importance of designing properties around how guests actually use them. Luke also shares practical lessons on building more durable rentals, including reinforcing bed frames, choosing furniture that can withstand heavy use, and avoiding unnecessary spending on expensive furnishings.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

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Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl explores the future of how guests discover and book short-term rentals, questioning why major real estate platforms like Zillow haven't embraced vacation rentals the way Google has with Google Vacation Rentals. He explains how the growing availability of property management websites, direct payment processing, and centralized calendars could make direct bookings increasingly common, potentially reducing booking fees for both guests and property managers. Luke predicts that over the next eight to ten years, consumers may increasingly find vacation rentals through major search platforms and then book directly through the property manager's website.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl demonstrates how he is using Claude's integration with PriceLabs to analyze his short-term rental pricing, compare his properties against market and competitor data, and identify opportunities to increase revenue. He walks through how AI can compare occupancy, average nightly rates, projected gross income, and custom seasonal base rates, while emphasizing that hosts need enough experience to ask the right questions and verify AI's recommendations rather than blindly trusting them. Luke also explores the potential for AI to eventually integrate with other STR software and function more like an AI property manager, making it easier for large property management companies to analyze data and manage their portfolios.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl is joined by Sally from Key Data to break down the current state of the short-term rental market and what the data says about the months ahead. They discuss how the unusual timing of Labor Day is shifting demand between August and September, why hosts shouldn't automatically slash rates when calendars look empty, and how understanding guest booking patterns, seasonality, and market data can lead to better pricing decisions. Sally also explains how metrics like RevPAR can help operators balance occupancy and rates, while emphasizing the importance of mystery shopping, monitoring cancellations, and adapting strategies for different types of last-minute and advance-booking guests.

How to connect with Sally:

keydata.co

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl discusses why investors should never rely on anyone to guarantee how much a real estate property will make, using the controversy surrounding Grant Cardone's real estate investments as a jumping-off point. Luke explains that while investors can make educated estimates using available data, there are too many variables—including market changes, interest rates, operating expenses, and an owner's own effort—to know a property's actual performance until it has been owned and operated for a meaningful period of time. He emphasizes that The Short Term Shop will never promise a specific revenue figure for a property and encourages investors to do their own homework, be conservative, and understand the risks before buying.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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 is joined by Richie Khandelwal, one of the founders of PriceLabs, to explore how the platform has evolved from manually entering thousands of nightly rates to becoming a powerful revenue management tool used by more than 700,000 homes worldwide. They discuss PriceLabs’ Listing Optimizer and its new AI integration, which allows hosts and property managers to connect PriceLabs with AI tools and use natural-language prompts to find data, analyze performance, and even take actions like adjusting rates or seasonal profiles. Richie emphasizes that AI can dramatically reduce the time spent managing pricing and portfolio data, but users should always verify its work and treat it like a highly capable intern rather than blindly trusting every answer.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl questions whether hosts have become too focused on asking guests for five-star reviews, arguing that constantly requesting feedback can come across as desperate and may even encourage negative responses. Using Disney's customer service as an example, he explains why delivering an exceptional guest experience should take priority over chasing reviews, and suggests that hosts be more selective about when they ask for feedback. Luke also encourages property managers to trust that genuine hospitality, thoughtful service, and authentic communication will naturally inspire guests to leave positive reviews without repeated reminders.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl explains why bad guest reviews are one of the most valuable tools for improving a short-term rental business, arguing that even unfair criticism often contains a lesson worth addressing. He discusses the importance of separating legitimate feedback from unreasonable expectations, reminds hosts that vacation rentals are homes—not hotels—and encourages property managers to use reviews as motivation to refine operations, strengthen the guest experience, and continually improve. Luke also reflects on how years in the business have taught him to respond with professionalism, focus on what he can control, and treat every review as an opportunity for growth.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl is joined by Holly from Killington Mountain Homes to discuss how she leveraged her background in the tech industry to build a high-performing short-term rental management company in Vermont. Holly shares how investing heavily in systems, staff training, in-house laundry operations, and owner communication has helped her properties consistently outperform the market, while explaining why genuine care, operational consistency, and a strong guest experience are the foundation for long-term success. The conversation also explores scaling a property management business, overcoming the challenges of a seasonal market, and building a brand that owners and guests can trust.

How to connect with Holly:

https://www.killingtonmountain.com/

@KillingtonMountainHomes on YouTube, Instagram, Facebook and TikTok

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl shares practical advice on planning and managing short-term rental rehabs, explaining why the offseason is the ideal time to tackle major projects and why new owners should resist renovating immediately after purchasing a property. He discusses the unique challenges of working with contractors in small vacation markets, encourages investors to learn their property before making costly upgrades, and emphasizes that patience, realistic expectations, and strong local relationships are essential for successful renovations. Luke also explains why starting with smaller projects can build confidence before taking on larger rehabs, while reminding listeners that consistent planning and organization are key to long-term success.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl explains why setting clear guest expectations—what he jokingly calls "guestspectations"—is one of the most important responsibilities of a short-term rental property manager. He argues that vacation rentals are homes, not hotels, and encourages hosts to communicate a property's limitations upfront, resist unrealistic guest demands, and avoid creating expectations that can't consistently be met. Luke also shares why online travel agencies should focus on being listing platforms rather than acting as property managers, while emphasizing that honest communication and proactive expectation-setting lead to better guest experiences and fewer conflicts.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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 continues his pricing series by explaining how to pair multiple base prices with customized minimum night stay profiles in PriceLabs to better match seasonal demand. He walks through how he adjusts minimum stays throughout the year, uses date-specific overrides for major holidays, and tailors orphan night strategies based on property size to maximize occupancy without sacrificing revenue. Luke also emphasizes that his recommendations are based solely on his own experience rather than affiliate partnerships, encouraging listeners to customize their pricing strategy to fit each property's booking patterns.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl shares an open-mic office hours session covering the mindset shifts that separate long-term success from short-lived wins in the short-term rental business. He encourages listeners to embrace abundance over scarcity, recognize that co-hosting is fundamentally property management, and avoid overpromising unrealistic revenue expectations that can't be sustained at scale. Luke also reflects on the sacrifices he and his wife made while building their real estate portfolio, reminding investors to be proud of where they are today, buy what they can afford, and trust that consistent hard work and patience will create future opportunities rather than chasing someone else's success.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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

Luke Carl discusses two common challenges in short-term rental management: guests who book the wrong dates and the growing demand for early check-ins. He walks through a real example of a guest who mistakenly reserved less expensive dates and later wanted to switch to higher-demand dates at the original rate, ultimately choosing to cancel and receive a courtesy refund despite being outside the cancellation policy. Luke also shares a new AI-powered workflow that proactively offers paid early check-ins when availability allows, creating an additional revenue opportunity while reducing repetitive guest requests. Throughout the episode, he emphasizes the importance of staying calm, following established systems, and keeping emotions out of recurring guest interactions that are simply part of the property management business.

How to connect with Luke:

The Short Term Shop -https://theshorttermshop.com/

Short Term Shop Plus -https://stsplus.com/

Follow us onInstagram

Follow us onTikTok

Join theShort Term Shop Facebook group

Check out theShort 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