If they think they have an "Airbnb" Unless they own the publicly traded company, then they only have a STR, or a vacation rental if they have a nice place/location.

At the courthouse, the tenant signed an agreement to vacate the property by December 1st.

(Luxury mansion or hosting your home while on a vacation)Have you noticed that your bookings are coming in a chunk?

Meaning you cannot just evict a tenant because their lease has expired.You will have to build sufficient evidence admissible in court and to the satisfaction of a judge to prove good cause to get a warrant of eviction.Many housing providers kept high risk tenants on month to month leases so that if the tenant stopped paying rent, you could simply give them a notice to vacate and recover possession of the rental unit that way.The reason for this methodology was because the HSTPA of 2019 passed in NYS made it extremely onerous and costly for housing providers to evict due to non payment.That method under good cause will be eliminated.So you can still keep tenants month to month but you will need to document the lease violation due to nonpayment rigorously.How many times and how late is “good” enough?

If those don’t align, vacation rental or investment property loans might be better options.

I personally have a few SF rentals but would love to get into more of the MF or even possibly short term vacation rentals someday.

Give her 30 days to vacate or start the eviction.

I could sometimes get in 5-7 days once a year for a vacation but I'd pay the price when I got back. 

One of my most profitable STRs ventures is not in a vacation market but it is a unique experience that is within an hour of a major metro hub.

I am a new investor who has been looking into the Jax Beach area for STR / vacation homes as an out of state investor.