Yes, you must file a 1099-NEC form with the IRS if you pay an unincorporated independent contractor $600 or more during a year for rental-related services. This includes payments to property managers and anyone else who performs services for your rental and is not your employee.
Beginning with the 2020 forms, copies of your 1099-NEC forms must generally be distributed and/or postmarked to independent contractors and other recipients by January 31. In 2021, however, the date is February 1 since January 31 falls on a Sunday.