Why Everyone Is Selling Their Short Term Rentals (And Why Savvy Investors Are Still Buying)
If you’ve been hearing whispers about short term rental owners selling en masse, you’re not imagining things. The headlines are everywhere, but there’s more to the story than panic and fear.
The truth? Short term rentals are still one of the strongest long-term investment strategies available. The challenge is that many people jumped in during the COVID travel boom without treating it like the business it is. As a result, they’re selling—but savvy investors are using this moment to buy, upgrade, and expand their portfolios.
In this post, we’ll cover:
Why many real estate investors sell within two years
How the 2021 boom distorted expectations
Why fewer sales today equal more opportunity
The realities of STR management (it’s a business, not gambling)
Why experienced investors are doubling down right now
The Two-Year Sell Myth: What’s Really Happening
A staggering portion of all real estate investments—not just short term rentals—are sold within two years. Some studies place this at nearly half of all deals. Why? Because many investors underestimate the realities of ownership.
New STR owners often assume they’ll buy a cabin, throw it on Airbnb, and watch money roll in. But that’s not how the business works. Short term rentals are closer to hospitality than passive investing. Without systems in place—or without treating it like a true business—investors get burned out or frustrated and sell early.
At The Short Term Shop, we train clients to do the opposite. With automation tools, remote management strategies, and resources like STS Plus, most of our owners spend less than an hour a week managing their properties. But that requires setup, knowledge, and accountability.
The 2021 Gold Rush: A Misleading Benchmark
Here’s where things really went sideways: 2021 was the best year ever for almost every STR owner. Travel surged as restrictions lifted, supply lagged behind demand, and bookings skyrocketed.
If you own a property for 50 years, you’re going to have one best year ever. For most, that year was 2021. The problem is that many buyers assumed the 2021 boom was the new baseline. When income dipped in 2022 or 2023, they panicked.
But the truth is:
49 out of 50 years won’t be your best year.
Real estate is cyclical.
Hospitality demand fluctuates seasonally and economically.
Those who expected a slot machine got spooked. Those who understood cycles adjusted pricing, tightened expenses, and kept operating. That’s why experienced investors—especially those using the short term rental tax loophole—are still confident.
The Current Market: Low Sales = High Opportunity
Let’s zoom out. Across the U.S., home sales hit their lowest levels in 30 years in 2023 and remain sluggish in 2025. That means inventory sits longer, sellers make concessions, and buyers with vision have leverage.
Why this matters for STR investors:
Less competition. Many retail buyers are sidelined by interest rates.
Better discounts. We’re seeing sellers accept price reductions just to move properties.
Timing the bottom. When transactions are at 30-year lows, it’s often the best entry point for long-term buyers.
In fact, this is the same playbook many used after 2008. Those who bought while everyone else sold ended up with life-changing portfolios.
If you’re considering investing, check out our guide on buying a short term rental in the Smoky Mountains or our post on buying in Broken Bow. Both markets illustrate the type of cyclical opportunity we’re seeing nationwide.
Short Term Rentals Are a Business (Not Gambling)
This is the number one reason people sell early—they bought thinking it was passive.
Here’s the reality:
STRs are not “set it and forget it.”
They are hospitality businesses. Guests expect communication, cleanliness, and attention.
The good news? They’re highly automatable. With the right systems, you can streamline cleaning schedules, guest communication, dynamic pricing, and even maintenance follow-ups.
At The Short Term Shop, we give every client the training and tools to self-manage. That includes vendor connections, automation software walkthroughs, and access to STS Plus, where thousands of investors share systems and solutions.
It’s not passive, but it is simple—and infinitely more profitable when done right.
Why Savvy Investors Are Still Buying
So, why are smart buyers doubling down while others sell?
They know downturns = opportunity. Historically, fortunes are made in down markets, not peak years.
They leverage tax strategies. Active management opens the door to the short term rental tax loophole, bonus depreciation, and serious W-2 savings.
They play the long game. Real estate isn’t about one good year—it’s about decades of wealth.
They understand automation. One hour a week to manage an appreciating asset with tax benefits? That’s a no-brainer for investors with vision.
FAQs
Why do so many investors sell within two years?
Because they weren’t prepared to treat STRs as a hospitality business. Without training and systems, most give up early.
Was 2021 an anomaly?
Yes. It was the “best year ever.” Expecting every year to perform like 2021 is like expecting every stock to perform like Tesla’s peak year. It’s unrealistic.
Is now really a good time to buy?
Yes. With sales at multi-decade lows, buyers have leverage, fewer bidding wars, and better opportunities to negotiate.
How do I manage without a property manager?
With the right systems. Our team specializes in teaching clients how to self-manage remotely in under an hour a week. STS Plus provides ongoing support.
Contact The Short Term Shop
Phone: 800-898-1498
Email: agents@theshorttermshop.com
Mentorship & Training: STS Plus
Podcasts & Market Insights: The Short Term Show
Disclaimer
This post is for informational use only and does not constitute financial or investment advice. Always consult a licensed advisor, CPA, or attorney before making any investment decisions.
