A 1099 would be required if the rental rises to the level of a "trade or business".
Unfortunately, there is no clear-cut answer to when a rental rises to the level of a "trade or business".
If the tenants are provided "services" (such as maid service or meals), it would be a "trade or business".
If the tenants are long-term (over 30 days) and you only have a single rental, most tax professionals view it as NOT a "trade or business".
If it is something between there, it depends on the facts-and-circumstances. But I suspect that if it is only one property (even if it is short term rentals), it would not rise to the level of a "trade or business" unless "services" are provided (in which case, as Don said, no 1099 would be required).
A couple of things to consider: (1) Are you claim the Qualifying Business Income Deduction (QBI)? If so, you might be claiming it is a "trade or business". (2) There isn't any harm in issuing a 1099, even if it isn't required. So if it is a "gray area", some people choose to file it to be on the 'safe side'.
