Put January 31 in your calendar now, and put a reminder two weeks ahead of it that says “vendor W-9s.” That single pair of entries prevents the one deadline small landlords blow most often, and it has nothing to do with filing your own return.
Tax dates feel like April. For a landlord they start in January and they are mostly about other people’s paperwork.
December: the work that makes January possible
Nothing is due. Everything that makes January survivable happens here.
Run your vendor payment totals for the year and see who is over the reporting threshold. Chase the missing W-9s while the vendors still have a reason to answer you. Reconcile the rental account so December’s transactions are categorized before the month closes, because the January version of that job competes with the 1099 deadline.
If you are close to the electronic filing threshold, check the count now. It is 10 returns, counted by aggregating all your information returns, and it has applied to returns required to be filed on or after January 1, 2024. Eleven forms cannot go in the mail.
January 31: Form 1099-NEC, both copies
Section 6071(c) puts Form 1099-NEC on or before January 31, on paper or electronically. The recipient copy goes out on the same schedule.
This is the tightest deadline on the calendar and the one with the least slack, because the information it needs comes from third parties. Whether a landlord has to file at all turns on whether the rental is a trade or business, and that is a question to have settled before the last week of January, not during it.
February 28 and March 31: Form 1099-MISC
February 28 if you file on paper. March 31 if you file electronically.
Form 1099-MISC is where rents you paid go, in box 1, along with a few other categories. Most small landlords who file anything file the NEC, not the MISC, but if you pay rent to a property owner or make certain other payments, this is your date.
April 15: the return, and the first estimate
Two things land together, which is part of why April feels heavy.
Your individual return is due, with Schedule E attached for the rentals. So is the first estimated tax payment of the new year, covering January 1 through March 31.
Filing an extension moves the return. It does not move the payment. That is the distinction that costs people money, every year, and it is worth stating plainly: an extension is an extension of time to file, not of time to pay.
June 15, September 15, January 15: the rest of the estimates
The IRS divides the year into four payment periods, and the due dates are uneven on purpose:
| Period | Due |
|---|---|
| January 1 to March 31 | April 15 |
| April 1 to May 31 | June 15 |
| June 1 to August 31 | September 15 |
| September 1 to December 31 | January 15 of the following year |
Note the second period is two months, not three. Landlords who set a quarterly reminder on calendar quarters miss June 15 by two weeks.
Estimated payments matter for a landlord because rental income arrives with no withholding attached. A salaried landlord whose day job withholds enough may owe nothing extra; a landlord whose rentals are the income usually does. Underpaying a period can produce a penalty even if you are due a refund at the end of the year.
The dates that are not federal
Two categories the calendar above does not cover, and both are local.
Property tax. Set by your county or municipality, on its own schedule, often in two installments. Your servicer may pay it from escrow, which is convenient right up to the year they do not. Confirm rather than assume.
State returns and local registration. State filing dates usually track the federal date but not always. Rental registration renewals, business license renewals, and city inspection schedules follow no pattern at all beyond the one your city set. Put each one in the same calendar as the federal dates, because that is the only place you will look.
If you miss one
Missing a date is not the same as being in trouble, and the response differs by which date it was.
A late information return is a penalty that scales with how late it is, which means filing a 1099 in February is meaningfully better than filing it in June, and filing it in June is better than not filing it. The worst move is deciding that because January 31 passed, the form no longer matters.
A missed estimated payment is priced as interest on the shortfall for the period it covers, so paying the next one early does not undo it but it does stop it growing. A missed return, with tax owed, accrues both a failure-to-file and a failure-to-pay charge, and the first is the larger of the two. That is the argument for filing on time even when you cannot pay in full.
In every case the fix is the same: file, pay what you can, and ask a CPA to price the exposure rather than guessing at it.
One clock this calendar does not run
Security deposit returns have their own statutory deadlines, set by state, and they are usually measured in days from the end of the tenancy rather than from a date on a calendar. They are unrelated to the tax year and they carry their own penalties, sometimes multiples of the deposit. What you can and cannot deduct from a deposit covers the substance; the deadline itself is a state-by-state question.
What to do with this
Enter six recurring reminders and stop thinking about it: mid-December for vendor totals and W-9s, January 31, February 28, April 15, June 15, September 15, and January 15. Then add your local dates.
The work behind each one is the same work: knowing what you collected, what you paid, and to whom, in a form you can total. Accounting in LeaseRooster keeps that current as it happens, and the tax season checklist runs the January-to-April sequence step by step.
This is general information, not legal or tax advice. Rules change and local ordinances vary. Confirm current requirements with your city, county, or an attorney before you act, and talk to a CPA about your own return.