I'm in Pinellas County, trying to expand my multifamily holdings, and it's tough to ignore the beach. Once you're at the beach, it's tough to ignore the allure of vacation rentals and the profit margins they have. I have read everywhere that Short Term Rentals, i.e. Airbnb, VRBO, etc are extremely difficult in many parts of FL, but especially in Pinellas County. Gulfport allows them, but SPB, Treasure Island, Clearwater, etc don't, and can be down right heavy handed in their enforcement according to some accounts. I'm aware of the status of the local law with regards to the state law, and that grandfathered STRs can continue to operate. 

Ok, now that all the reasons we can't do it are out of the way, how do we get around them? I know there are STRs in these beach communities, and I'm certain some have traded hands over the years. Some are probably operating illegally, and there might be some merit to that, but I'm looking for legal methods first.

Do you operate as a hotel? How tough is that process, and what kind of costs am I looking at? 

Is there some other permit to obtain? 

EDIT: Mods, I posted this in the wrong spot. I meant to post in the St Petersburg Forum. Would someone mind moving it? Thanks!