If I own rental property, and hired a contractor in 2020, do I have to file form 1099-ENT with the IRS?

Yes, rental property owners must report payments of over $600 to independent contractors, limited liability corporations (LLC's) and some C corporations. That includes plumbers, electricians, gardeners, housekeepers and more. All you need is their address and tax ID number, or a W-9 form.

There are strict reporting guidelines, and you are not allowed to print the form on your own printer (electronic reporting is encouraged).

For 2020 the deadline is February 1st 2021, though some states like California don't demand the forms until February 28th 2021.

For 2020 the IRS will share form 1099-MISC with the states, but not 1099-ENT. Thus, on a state-by-state basis you may have to file separately with the home state of the contractor. See this helpful guide https://sovos.com/blog/2021/01/06/latest-updates-state-direct-reporting-requirements-for-form-1099-nec/

If you can't get the contractor to cooperate see How can I send a 1099-Misc if a contractor won't provide an EIN or SSN?