Maximizing Holiday Income with Short-Term Rentals: Tips from Avery Carl, CEO of The Short-Term Shop

As Halloween decor gives way to winter holiday fare, with spider webs replaced by twinkling lights and pumpkins by snowmen, that’s a clear indicator for savvy investors that the holiday short-term rental boom is approaching.

We sat down with Avery Carl, CEO of The Short Term Shop and one of the most eminent figures in the short-term rental industry, to discuss seasonal market fluctuations and ways in which investors can take advantage of the ebbs and flows of supply to maximize revenue.

Named in Wall Street Journal’s top ten real estate agents this year, Carl began her investment journey with a single vacation property in 2015. In less than a decade, she has grown her portfolio to over 250 properties and overseen the sale of more than $2.5 billion worth of short-term and vacation rentals. From this extensive experience, Carl has distilled three key principles for boosting revenue during the holiday season:

1 – Modify Your Pricing To Account For Seasonal Fluctuations

With short-term rentals, you simply can’t rely on the model of setting the price yearly and forgetting about it like you can with long-term rentals. As Carl explained, “Short-term rentals are a lot more hands-on. Pricing-wise, you should have different rates for weekends versus weekdays and low and high seasons.”

The average American takes about 10 to 14 vacation days per year, and these tend to aggregate around major holidays like Thanksgiving, the 4th of July, and Christmas. According to Carl, investors need to discern how these major holidays affect their own markets.

“Pay close attention to the holidays that directly correlate to shrinking supply in your area, because they’re going to be different depending on the market,” said Carl, “If you’re in a winter holiday destination, your biggest boom might happen in December and January, whereas if you’re at a beach destination, it might happen in the middle of summer.”

Adequately pricing properties is not an exact science but a well-informed approximation. That’s why Carl suggests frequently visiting the same booking platforms that potential renters use and evaluating how your property measures up against others, using a process that Carl coined called “The Enemy Method.”

“Market conditions not only change with the seasons but also fluctuate due to other economic factors,” said Carl, “One month, you might be facing a high-supply market due to several new rental properties hitting the market. Or there might be a squeeze in the supply due to a big upcoming festival or conference. But you might not know about either situation unless you’re routinely using The Enemy Method to check how you stack up against other properties.”

As Carl explained, the good news is that there are now many dynamic pricing tools on the market, such as Price Labs, that can optimize pricing based on countless data points in mere seconds, so engaging in variable pricing has never been easier.

2 – Increase Holiday Bookings by Adding Amenities And Personal Touches

Everyone has a story of staying at an amazing vacation rental where the host went above and beyond to make guests feel welcome, whether it was by leaving behind a small gift, like a gift basket, or making sure that the home was not only immaculate but also cozy and equipped with all the comforts that made it feel like a home away from home.

“Short-term investors sometimes make the mistake of pricing their property based almost exclusively on amenities and number of bedrooms. But decor and ambiance should also be taken into account,” Carl emphasized, “It’s very important, especially during the holidays, to make guests feel like they’re in a space where they can celebrate a special occasion.”

According to Carl, even simple gestures, such as providing guests with a cookie or hot chocolate bar for a special evening or arranging subtle winter holiday decorations, can create a positive ripple effect. Because happy guests often leave glowing reviews, which, in turn, enhances your property’s visibility in booking platform search engines.

3 – To Score a Winning Match, Give Your Rental Brand a Makeover 

Short-term rental investors can elevate their property’s perceived value by charging a bit more, as guests often associate higher prices with a premium experience, but the experience will have to back that up, and it will need to be reflected in the listing photos.

Per Carl, to position your rental as a luxurious option compared to others in your area, ensure that your property has high quality professional photos. DIY cell phone photos do not exude a professional appearance.

“New short-term investors can sometimes undervalue the importance of great photos, but these can make all the difference,” said Carl, “I once had an investor who suddenly stopped getting bookings. As we came to find out, what had changed was that the first photo shown on her listing had been accidentally replaced by a picture of the beach instead of her property. That first image mattered enough to cause a sudden drop in bookings, because it didn’t give any sort of representation of the property itself, and potential guests were just scrolling past the listing..”

According to Carl, presentation and style is increasingly more important the higher up you go in price, but it’s not just about appearances. Professionalism also applies to your communication. Being friendly and responsive in your interactions, both before and after booking, makes guests feel well cared for. The higher the level of service you provide, the more you can justify charging a premium.

About Avery Carl

Avery Carl, Founder of The Short Term Shop brokered by EXP, was named one of Newsweek’s Top 500 agents in 2020, Wall Street Journal’s Top 100 in 2021, Top 50 in 2022, and Top 10 in 2023, as well as the New York Times Top 100 in 2022. She and her team focus exclusively on vacation rental and short-term rental clients, having closed well over $2.5B in sales. To join over 5,000 happy Short Term Shop investors, please visit https://theshorttermshop.com/