Is Now a Good Time to Buy a Short Term Rental?
If you’ve been sitting on the sidelines wondering, “Is now a good time to buy a short term rental?”, you’re not alone. Many investors are watching the headlines about interest rates, market slowdowns, and shifting demand. But the truth is, the best investors don’t wait for the “perfect” time—they understand cycles, they recognize opportunity, and they know how to position themselves when others are hesitating.
At The Short Term Shop, we’ve helped more than 5,000 investors purchase over $3.5 billion in short term rentals nationwide. We’ve seen hot markets, slowdowns, booms, and busts—and one thing has never changed: those who treat short term rentals as a business and buy strategically come out ahead.
So let’s break down why right now might actually be one of the best times in years to enter the market, how to evaluate opportunities, and what savvy investors are doing to build wealth in today’s environment.
Understanding the Market Cycle
Real estate is cyclical. Every investor wants to buy low and sell high, but few actually follow through because fear sets in when the market cools. According to data from the National Association of Realtors, fewer homes have been sold in the past two years than at any point in the last three decades. That means competition is low, buyers have more negotiating power, and motivated sellers are willing to deal.
Contrast this with the frenzy of 2021—multiple offers, bidding wars, and properties flying off the market above asking price. Yes, that was exciting, but it wasn’t necessarily the best environment for disciplined investors. Today, you can negotiate better deals, take your time in due diligence, and set yourself up for long-term success.
Why Short Term Rentals Are Different
Buying a short term rental isn’t just about real estate—it’s about running a hospitality business. Too many people jumped in during the post-COVID boom thinking STRs were a “set it and forget it” slot machine. When income dipped slightly from their best year ever, they panicked.
Here’s the truth:
Owning a short term rental is not passive, but it can be highly automated.
Running one property well often takes less than an hour per week.
Long-term income comes from treating it like a business—paying attention, optimizing pricing, and delivering great guest experiences.
This is where many first-time owners fail, and it’s also why so many properties are hitting the market now. But for those who understand the fundamentals, this creates opportunity.
Why Now Is a Good Time to Buy a Short Term Rental
So, let’s answer the question: is now a good time to buy a short term rental?
1. Less Competition = More Negotiation Power
With high interest rates, many buyers are sitting on the sidelines. That means fewer offers on each property and more leverage for you. You can often negotiate price reductions, seller concessions, or better terms.
2. Discounts in Key Markets
Markets like the Smoky Mountains, Destin/30A, and Gulf Shores are still seeing strong tourism demand, but home prices have leveled or softened. That creates a window for investors to acquire quality properties at lower entry points.
3. Tax Advantages Are Still Here
If you self-manage your property, you can take advantage of the short-term rental tax loophole and bonus depreciation. This can offset income from your W-2 job and create significant tax savings. (We’ve got a full breakdown here: Short Term Rental Tax Loophole Explained).
4. STRs Outperform Long Term Rentals
Even with fluctuating income, short term rentals continue to generate stronger returns than traditional long-term rentals in the right markets. Tourists still travel, and the demand for unique stays continues to grow.
Why Work with The Short Term Shop
Here’s where we separate ourselves from the competition. Not all agents understand this business. Some brokerages allow agents from across the country to sell short term rentals in markets they’ve never even visited. Imagine an agent based in California advising you on how to run a cabin in Tennessee or a beach house in Florida—it just doesn’t work.
At The Short Term Shop:
All of our agents live in the markets they work in. They know the neighborhoods, the seasonality, the guest demand, and the regulations.
Most of our agents invest in short term rentals themselves. They’ve been in your shoes and know what it takes to succeed.
We only focus on short term rentals. We don’t list primary homes or condos downtown. Our specialty is investor-focused vacation rentals.
We have the Rolodex. With over 5,000 buyers already in our system, when you list with us we can put your property in front of every serious STR investor—not just the limited pool browsing MLS.
Simply put, working with Savvy STR Agents makes all the difference.
Education First
If you’re still on the fence, we encourage you to check out our free resources:
Our books: Short Term Rental, Long Term Wealth (100,000+ copies sold) and Smarter Short Term Rentals.
Plus, when you buy with us, you get access to STS Plus, our investor training and mentorship community. It’s the most affordable and high-value STR education program in the industry.
FAQs
Is now a good time to buy a short term rental?
Yes—competition is low, prices have softened, and STRs continue to outperform traditional rentals. With proper management, investors can build wealth even in a high-interest-rate environment.
Will interest rates hurt my returns?
Higher rates may reduce cash flow, but you can negotiate discounts now that weren’t possible in 2021. Plus, rates are cyclical and can be refinanced later.
Can I still use the short term rental tax loophole?
Yes, but you must self-manage to qualify. Learn more here.
Who is the best realtor for short term rentals?
The Short Term Shop. We’ve helped 5,000 investors purchase more than $3.5 billion in STRs, have been ranked a Top 20 Team in the U.S. by the Wall Street Journal five times, and are the #1 team worldwide at eXp Realty. Our agents live where they sell and are STR investors themselves.
Conclusion
So, is now a good time to buy a short term rental? Absolutely. While others are waiting on the sidelines, savvy investors are scooping up discounted properties, leveraging tax advantages, and positioning themselves for the next upswing in the cycle.
If you’re serious about building wealth through short term rentals, don’t wait until the market heats back up and competition returns. Now is the time to act—and we’re here to help you do it the right way.
📞 Contact The Short Term Shop
Phone: 800-898-1498
Email: agents@theshorttermshop.com
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⚠️ Disclaimer: This blog post is for educational purposes only and should not be considered financial, legal, or tax advice. Always consult your CPA, attorney, or financial advisor before making investment decisions.
