Can a legal Miami Beach short term rental permit trump HOA ban?

[Jean H.]

A realtor contact, knowing that I have several short term rental ("STR") properties, sent me the listing for a potential Airbnb property. It's a townhouse in Miami Beach (very hot Airbnb destination but where illegal Airbnbs can be fined $20,000 per violation). The owner was able to get an STR license so he actually had a legal STR going in Miami Beach. Unfortunately, according to the realtor, the HOA just passed a resolution banning STRs. The realtor insists that this property has been grandfathered in and can continue to be an Airbnb for the new owner. I am skeptical.

I would only be interested in this property if I would be able to Airbnb it out since having a legal Airbnb in Miami Beach is very valuable (and lucrative, because of the scarcity value).

So two questions for you Florida attorneys (especially those in Miami):

1) Who trumps who? The city or the HOA? My gut feeling is that I need both on board in order for me to legally rent it out on Airbnb--that I would need a STR-friendly HOA Board AND a Miami Beach STR license. Can the STR license truly be "grandfathered in" and trump the ban imposed by the HOA?

2) Even if the STR license is grandfathered in, would that license (or the ability to get the license) transfer over to a new owner? or would it only work for the current licensee?

Would love to hear your thoughts, BP community!

Jean