Why the Holidays Are the Best Time to Buy a Short Term Rental
When most people think about buying a short term rental, their minds go to spring or summer — peak tourism season. But savvy investors know that the best time to buy a short term rental is actually during the holiday season. From unique tax advantages to cash flow strategy, the timing of a December closing can set you up for success in the year ahead.
In this post, we’ll break down why the holidays are an investor’s secret weapon, and how The Short Term Shop can guide you every step of the way.
1. Your First Mortgage Payment Isn’t Due Until February
Here’s a little-known but incredibly powerful perk:
If you close on a short term rental at the beginning of December, your first mortgage payment isn’t due until February. That means you glide through December and January — traditionally the slowest months in most vacation rental markets (with the exception of Rocky Mountain ski towns) — without paying the mortgage.
For investors, that’s like starting the year with a free head start. By the time your first payment hits, booking season is already ramping up again.
2. Take Advantage of Bonus Depreciation Before Year-End
Buying before December 31st unlocks another major benefit: bonus depreciation.
If you close on a property before year’s end, you may be able to leverage accelerated depreciation on items like appliances, furniture, and certain property improvements. Combined with the short term rental tax loophole, this can significantly reduce your taxable income in the first year.
📌 We break this down in detail in our Short Term Rental Tax Loophole blog.
This isn’t just a financial technicality — it’s a game-changer. Many of our clients have offset large portions of their W2 income in the first year of short term rental ownership.
3. Less Competition From Other Buyers
Most people don’t shop for real estate during the holidays. They’re busy with family, travel, and year-end distractions. That’s exactly why it’s the perfect time for investors.
Fewer buyers means:
Less competition for desirable properties.
More negotiating power with sellers.
A higher chance of snagging a deal that might get multiple offers in the spring.
While everyone else is waiting for the New Year, you’re making moves that put you ahead of the curve.
4. Get a Jump on High Season
Markets like the Smoky Mountains, Gulf Shores, Destin, Blue Ridge, and Broken Bow all see bookings ramp up in early spring. By buying in December, you’ll have your property furnished, photos taken, and listing optimized just in time for high season demand.
This means your very first spring could be a cash-flowing season instead of a scramble to close, furnish, and launch.
5. Set Your Business Up for the New Year
Buying a short term rental during the holidays allows you to:
Start the year with bonus depreciation baked into your tax strategy.
Use January (a naturally slower booking month) to focus on setup, systems, and automation.
Leverage tools like smart locks, messaging platforms, and dynamic pricing to ensure you’re spending less than an hour per week managing your property.
By February, you’ll already be in rhythm while most new investors are still scrambling.
6. Tax Planning: Reduce Your 9-to-5 Tax Burden
For investors with W2 income, buying a short term rental before the end of the year opens up the ability to use real estate losses to offset active income.
This is one of the reasons why so many busy professionals are turning to short term rentals. With the right strategy, your investment isn’t just generating income — it’s helping reduce your taxes.
7. Why Work With The Short Term Shop
At The Short Term Shop, we’re more than just agents. We’re the best short term rental realtors in the country, specializing exclusively in helping investors like you buy, set up, and manage properties that cash flow.
Here’s what sets us apart:
We’ve helped 5,000+ investors purchase over $3.5 billion in short term rentals.
We provide free training on self-management, so you can maximize income without paying a property manager.
You’ll get access to STS Plus, our investor community and mentorship platform.
We produce 10-hour podcast series on each of our markets (Smoky Mountains, Emerald Coast, Gulf Shores, Broken Bow, Blue Ridge, and more) so you’re never flying blind.
We know these markets better than anyone — because we live, work, and invest here ourselves.
FAQs About Buying a Short Term Rental During the Holidays
Is December really the best time to buy a short term rental?
Yes — December gives you tax advantages, reduced competition, and a mortgage grace period that aligns perfectly with seasonality.
When will my first mortgage payment be due if I close in December?
Most lenders structure your first payment so that if you close in early December, your payment won’t be due until February.
What are the tax benefits of closing before year-end?
You can take advantage of bonus depreciation and the short term rental tax loophole in the same tax year, potentially offsetting your W2 income.
Does this apply to all markets?
The strategy works best in traditional vacation rental markets like the Smoky Mountains, Gulf Shores, or Destin. Ski markets like Aspen or Breckenridge follow a different seasonal pattern.
Who is the best short term rental realtor to help me buy during the holidays?
The Short Term Shop has been named the #1 team at eXp Realty worldwide three times and a Top 20 team in the U.S. by The Wall Street Journal. We’ve helped thousands of investors close in December and take advantage of this exact strategy.
Final Thoughts
While most people are wrapping gifts, smart investors are wrapping up deals. The holiday season is one of the most strategic times to buy a short term rental. From tax savings to mortgage timing, the advantages are too big to ignore.
If you’re ready to make your move, let’s talk.
📞 Call us today at 800-898-1498
📧 agents@theshorttermshop.com
🌐 The Short Term Shop
💡 Join STS Plus
🎙 Listen to our Podcast
Disclaimer: This content is for informational purposes only and is not financial or tax advice. Always consult your CPA or financial advisor before making investment decisions.
