Staffing a short-term rental: contractor or employee?

The label on the invoice decides nothing

• Behavioral control — "Does the company control or have the right to control what the worker does and how the worker does his or her job?"
• Financial control — "Are the business aspects of the worker's job controlled by the payer? (these include things like how worker is paid, whether expenses are reimbursed, who provides tools/supplies, etc.)"
• Type of relationship — "Are there written contracts or employee type benefits (that is, pension plan, insurance, vacation pay, etc.)? Will the relationship continue and is the work performed a key aspect of the business?"

Why rental cleaners sit in the awkward middle

Run the three categories against a typical turnover cleaner and the answers stop being comfortable.

Behavioral control: you specify the checklist, the photographs, the linen standard and the window between checkout and check-in. That is instruction on how the job is done, not just what result you want.

Financial control: many owners supply the vacuum, the linens and the consumables, and pay a flat fee per turn with no realistic opportunity for the cleaner to make a profit or a loss on the engagement.

Now run the same three questions against a cleaning company that serves twenty properties, brings its own equipment, sets its own methods, invoices on its own terms and carries its own insurance. The answers flip on all three. That contrast, rather than the hourly rate or the word on the invoice, is the thing that decides status.

The paperwork that protects a genuine contractor relationship

If the relationship really is contractor, the administration is light and the discipline matters. Before the first payment, have the contractor complete Form W-9, Request for Taxpayer Identification Number and Certification, to get the correct name and TIN. Keep it on file for four years.

If you got it wrong

The order of preference is obvious once written down: classify correctly now, fix it voluntarily if you did not, and do neither of those things in the middle of an audit.