Is Now a Good Time to Buy a Short Term Rental?

The Short Term Shop
Published: December 26, 2025
Getting Started

Summary

This article from The Short Term Shop argues that now is a good time to buy a short-term rental due to less competition, softening prices in key markets, and continued tax advantages. Hosts should consider this information when evaluating market conditions and investment opportunities.

Key Insights

  • If you self-manage your property, you can take advantage of the short-term rental tax loophole and bonus depreciation.
  • Fewer homes have been sold in the past two years than at any point in the last three decades, meaning competition is low and buyers have more negotiating power.
  • Markets like the Smoky Mountains, Destin/30A, and Gulf Shores are seeing strong tourism demand, but home prices have leveled or softened, creating an opportunity for investors.

Action Items

  • Self-manage your property to qualify for the short-term rental tax loophole.
    Effort: medium
    Impact: high
  • Consider negotiating better deals on property purchases, taking your time in due diligence.
    Effort: medium
    Impact: medium

Tools & Resources

  • Short Term Rental, Long Term Wealth: Also check out their books: "Short Term Rental, Long Term Wealth" and "Smarter Short Term Rentals".
  • The Short Term Shop: Check out The Short Term Shop's free resources including "Buying a Short Term Rental on the Emerald Coast" and "The Short Term Rental Tax Loophole".(theshorttermshop.com)

Common Mistakes

  • Many first-time owners fail by not treating their STR like a business, and many properties are hitting the market now because of it.

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