Before You Buy a Short-Term Rental

A lot of investors get stuck in “learning mode.” Tools and data help — if you know how to use them.

Privy is offering a limited-time bundle that combines both: three months of the Privy software plus their Residential Investment Academy for $100. The software pulls live MLS, public records, rental data, and real investor comps into one place. The Academy shows you how to turn that data into a clear buy box, accurate comps, and a weekly habit of making real offers.

If you’re ready to move from studying deals to actually pursuing them, this is a clean way to do it.
👉 Click here to learn more.

Short-Term Great Returns? Long-Term Headache?

Short-term rentals can look great on paper.

Higher nightly rates.

Strong gross returns.

Impressive screenshots on social media.

But the real question isn’t can they make money.

It’s whether the returns are worth the complexity.

Short-term rentals are not just a different asset class — they’re a different business.

What You’re Really Signing Up For

Compared to long-term rentals, short-term properties introduce:

  • Constant guest turnover

  • Cleaning coordination and quality control

  • Furnishing, repairs, and accelerated wear

  • Reviews that directly affect income

Even with a property manager, the oversight doesn’t disappear — it shifts.

The Regulatory Risk

Local regulations are the wild card.

Cities can—and do—change rules quickly:

  • Permit caps

  • Zoning restrictions

  • Primary-residence requirements

  • New taxes and fees

A property that works beautifully today can become illegal—or far less profitable—tomorrow.

Long-term rentals rarely face that kind of existential risk.

When Short-Term Rentals Can Make Sense

STRs tend to work best when:

  • You’re in a proven, regulation-stable market

  • You treat it as an operating business, not passive income

  • You’ve priced in management, vacancy, and friction

  • You’re comfortable with income volatility

If your model depends on perfect occupancy or constant rate growth, it’s fragile.

The Trade-Off

Long-term rentals trade upside for stability.

Short-term rentals trade stability for upside.

Neither is “better.”

They simply reward different temperaments.

Before choosing, ask yourself:

  • Do I want higher returns—or fewer surprises?

  • Am I investing—or running a hospitality business?

  • Would this still work if rules tighten?

The best investment is the one that fits your tolerance for complexity, not someone else’s spreadsheet.