Tax Planning Calendar for STR Hosts: Month-by-Month Guide
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STR taxes aren’t just a once-a-year event — they require action every quarter, and the biggest opportunities (like timing a major purchase for bonus depreciation or hitting your material participation hours before year-end) require you to be paying attention throughout the year. This month-by-month guide tells you exactly what to do and when.
Q1: January – March
- Pay Q4 estimated taxes by January 15 (for prior year Q4 income)
- Issue 1099-NEC forms to all contractors above the filing threshold by January 31 — $600+ for 2025 payments (file by Jan 31, 2026); $2,000+ for 2026 payments
- Collect any outstanding W-9 forms from cleaners and contractors
- Review and reconcile all prior year income — verify totals against your Airbnb 1099-K
- Organize all receipts and expense records from the prior year
- Review your material participation hour log for completeness
- File 1099-NEC forms with the IRS (February 28 paper; March 31 electronic)
- Gather all income documents: Airbnb 1099-K, VRBO 1099-K, direct booking records
- Compile your complete expense log with categories mapped to IRS categories
- Prepare asset purchase list for CPA: items bought during the year with dates and costs
- Prepare your hours log for material participation documentation
- File your tax return or file an extension by April 15 (extension gives you until October 15, but doesn’t extend payment due dates)
- Deliver complete tax package to CPA by March 1 for April filing
- Review prior year depreciation schedules — verify all assets are being depreciated
Filing an extension moves your filing deadline to October 15, but your payment is still due April 15. If you file an extension but owe taxes, you’ll owe interest on any unpaid balance from April 15 forward. Estimate your liability and pay by April 15 even if you extend.
Q2: April – June
- File tax return or extension by April 15
- Pay Q1 estimated taxes for the current year by April 15
- Open a new expense tracking period — reset your systems for the current year
- Confirm you have W-9s from all new cleaners or contractors hired this year
- Mid-year income and expense review — are you on pace with estimates?
- Check material participation hour count — are you on track for 100+ or 500+?
- Pay Q2 estimated taxes by June 16
- Review any major expenses you planned for the year — timing matters for depreciation
Q3: July – September
- Review peak season income — adjust Q3 estimate upward if revenue is tracking high
- Check material participation hour pace — if short of 100 hours with 5 months left, increase hands-on management now, and confirm you're still ahead of your cleaner or property manager's hours
- Consider if a cost segregation study makes sense for any recent purchases
- Plan major Q4 purchases (furniture, appliances, tech upgrades) to maximize depreciation in current year
- Pay Q3 estimated taxes by September 15
- Begin year-end planning conversations with your CPA
- Review contractor payments year-to-date — identify anyone approaching the $2,000 1099-NEC threshold for 2026 payments
- October 15: Extended tax return deadline (if you filed an extension in April)
Q4: October – December
- Make planned equipment and furnishing purchases to place assets in service before December 31 for bonus depreciation
- Confirm your material participation hour count — make sure you’re hitting your threshold before December 31
- Review and execute any year-end tax strategies with your CPA (Roth conversions, retirement contributions, etc.)
- Stock up on guest supplies in November or December to capture those expenses in the current tax year
- Finalize all year-end purchases by December 31
- Review your participation hours log — fill any gaps while memory is fresh
- Ensure all contractor payments are recorded and W-9s are on file
- Take year-end photos or video of the property (useful for insurance and documentation)
- Holiday stocking: welcome supplies, seasonal amenities — deductible in the year purchased
The last quarter is where proactive STR tax planning earns the most money. Accelerating deductible purchases, confirming material participation hours, and planning large capital improvements can shift thousands of dollars of deductions into the current year. Don’t wait until January to think about this.
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Disclaimer
This article is for informational purposes and does not constitute tax, legal, or financial advice. Tax rules vary based on your specific situation, filing status, entity structure, and jurisdiction. Always consult a qualified CPA or tax professional for guidance on your specific tax situation. IRS rules and thresholds are subject to change — verify current requirements at irs.gov before filing.
Frequently Asked Questions
When are quarterly estimated taxes due for STR hosts?
Quarterly estimated tax payments for 2026 income are due: Q1 — April 15, 2026; Q2 — June 16, 2026; Q3 — September 15, 2026; Q4 — January 15, 2027. If the due date falls on a weekend or holiday, it shifts to the next business day. Pay via IRS Direct Pay at irs.gov/directpay. Missing payments triggers an underpayment penalty even if you pay in full at filing.
When do I need to file 1099-NECs for my cleaners and contractors?
Form 1099-NEC must be provided to the recipient and filed with the IRS by January 31 of the year following payment. For contractors paid in 2026, the deadline is January 31, 2027. You must file electronically if you have 10 or more 1099s. To meet this deadline, collect W-9 forms from all contractors before making the first payment — not in January.
When should I make large equipment purchases for bonus depreciation?
To claim bonus depreciation or Section 179 expensing on equipment, the asset must be placed in service (purchased and available for use) before December 31 of the tax year. Make any planned major purchases — furniture, appliances, smart home equipment — by mid-December to ensure delivery and installation before year-end. Assets merely ordered but not received by December 31 generally do not qualify for that year's deduction.
What should I review in mid-year for my STR taxes?
A mid-year STR tax review should cover: (1) year-to-date income vs. quarterly payment pace, (2) material participation hour count and whether you're on track for 100 or 500 hours, (3) expense categories to catch any missing receipts while they're still findable, (4) whether any major purchases planned for the year should be accelerated to maximize deductions, and (5) whether your estimated tax payments need adjustment.