Tax Playbook · Investment tax wins
The short-term rental loophole
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This is an aggressive strategy, so work with a tax professional. If guests stay seven days or fewer on average and you truly run the property yourself, rental losses can offset your W-2 wages. A cost segregation study can turn a $100,000 paper loss into a real tax cut. Other limits like basis and at-risk rules can still shrink the loss.
Good for: High earners who own (or want) a vacation rental.
Learn the basics
Recent articles & guides
- White Coat Investor: Cost segregation
- WCG: Short-term rental tax loophole
- Fraim CPA: STR loophole — offset income with rental losses
- Landlord Studio: The short-term rental tax loophole
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Educational summary, not tax advice. Limits and rules change — confirm current law with your tax adviser.