Stock Island STR vacation home

[Brent Benoit]

Hello all! 
I have been vacationing in Stock Island/ Key West for 10 years or so. Now I am older and looking to buy an actual house to stay in, and not a tent. But of course, when I am not there, I would like to rent it out so it will pay for itself. 
My plan is to do a cash out refinance on a rental property I own in Butler, pa. Take out 100,000 from that. Use $50,000 or less as a 10% down payment, the other $50,000 would be used for closing costs, refurnishing, outfitting it for a STR, and paying the mortgage and bills for a couple months to get it up and running.
I feel this is more of an appreciation investment, than cashflow. Which is fine. As long as it pays for itself and I have a place to stay. 
My question is, do y’all think this is a wise use of a cash-out-refinance? 
What do y’all know about STR’s in the lower Florida Keys? Are the municipalities friendly to it? 

Any thoughts or suggestions are helpful! 
please let me know if you need any more info from me! 

Brent Benoit