Every January a chunk of STR owners realize they paid their cleaner $3,200 last year, never got a W-9, and the cleaner is “not available to talk.” 1099-NEC isn’t optional, the penalty stack is real, and the fix is a 90-second conversation that has to happen before you cut the first check — not at year-end.
Who actually gets a 1099-NEC
The clean rule: any non-corporate contractor you paid $600 or more during the calendar year for services rendered in the course of your trade or business gets a 1099-NEC. For STR owners, that almost always means:
- Cleaners and turnover crews (sole proprietors and most LLCs)
- Handymen, plumbers, electricians paid directly (not through their company-billed account)
- Lawn care and landscapers
- Property managers if you pay them as independent contractors
- Bookkeepers, copywriters, photographers
- Co-hosts you pay a share or fee to
Who does NOT get a 1099-NEC:
- C-corporations and S-corporations (with limited exceptions — legal and medical services to corporations still get reported)
- Anyone you paid by credit card or third-party network (Venmo business account, PayPal goods/services, Stripe). Those payments are reported by the processor on 1099-K and you don’t double-report.
- Anyone you paid less than $600 cumulative for the year
- Personal expenses unrelated to the STR
The credit-card carve-out is the one that surprises operators. If you ran every cleaner payment through a business credit card or Venmo business, you don’t issue 1099-NECs for those payments. They’re already reported. ACH transfers, paper checks, cash, and personal Venmo are the ones that fall on you.
The W-9 has to come first
The mistake nearly every host makes once: paying the cleaner for a month, then asking for a W-9 in January when they need to issue the 1099. By that point you have no leverage. The cleaner ghosts, the W-9 never comes, you don’t have a TIN to put on the form, and you’re filing a 1099 with “REFUSED” in the TIN box — which triggers backup withholding of 24% you should have been withholding all along.
The fix:
No W-9, no first invoice paid. Make it a precondition of the business relationship. The cleaner who refuses to sign a W-9 is telling you something you need to hear before they have keys.
The W-9 itself is one page. It captures their legal name, business name (if different), federal tax classification (sole prop, LLC, corp, etc.), and TIN (SSN or EIN). Once you have it, you don’t ask again unless their info changes.
The deadline that has actual teeth
- January 31 — Copy B to the contractor and Copy A to the IRS. Same deadline for both. This is not the same as the W-2 / 1099-MISC late February deadline you may remember from years past.
Penalties (per form, per year, indexed):
| How late | Penalty per form |
|---|---|
| Within 30 days | ~$60 |
| After 30 days, before Aug 1 | ~$130 |
| After Aug 1 or never filed | ~$330 |
| Intentional disregard | ~$660 (no cap) |
If you missed one cleaner for one year, you’re out a couple hundred dollars. If you missed five contractors for three years and the IRS finds it during another audit, you can be six figures into penalties before the underlying tax issue is even discussed.
The two forms that have to go out
- 1099-NEC to each qualifying contractor — Copy B to them by January 31, Copy A to the IRS by January 31 (electronic or paper).
- Form 1096 — the transmittal cover sheet, paper filers only. Electronic filers via the IRS IRIS system skip 1096.
Most operators with more than five 1099s should file electronically. The 2024+ regulations dropped the e-file threshold to 10 total information returns (counted in aggregate, not per form type) — so a host with 6 cleaner 1099s and 5 handyman 1099s is required to e-file.
The expense side
When you issue a 1099-NEC, the payment is deductible as a contractor expense on Schedule E (line 11, “Management fees” or, more correctly, typically reported as “Cleaning and maintenance” depending on the service) or Schedule C if the activity is reported there. The 1099 is not the deduction — the underlying payment is. But the deduction is much harder to defend if the contractor isn’t 1099’d, because the auditor’s first question is “show me the W-9 and the 1099 for this payee.”
The 30-day cleanup if you’re behind
If you realize in February or March that you didn’t issue 1099s for last year:
- Pull every cleaner / contractor / property-related payee paid by non-card method.
- Total each payee’s payments. Anyone over $600 is on the list.
- Request W-9s immediately. State the deadline.
- File 1099-NEC and 1099 copies as soon as you have TINs.
- Pay the late-filing penalty (will be billed automatically), don’t wait for a notice.
- For next year — W-9 first, payment second. Lock it in.
Where the workbook helps
The 1099-NEC Tracker — $17 — holds a row per contractor with W-9 on-file status, year-to-date payment total against the $600 threshold, and a “card-paid vs cash/ACH” split so you only generate 1099s for payments that actually require one. January is supposed to be filing, not reconstruction.
Not ready for the tracker yet? Grab the free 47 STR deductions checklist — it lists the contractor and service categories most hosts under-report, so you know which payees to be chasing W-9s from in the first place.
This is general information, not tax advice. The $600 threshold, the e-file count, and the corporate exception interact with your specific facts — your CPA’s call before you file.