@Matthew Ranucci I just went through this process last summer! Celebrity Home Loans helped me with the 10% down vacation home loan (I believe they offer 15% down as well). Great market to be in right now!
If you're looking into doing STR as your mentioned, then I recommend Gulfport, FL located 5-10 minutes away from Downtown St Pete. It is not regulated like much of Tampa/St Pete and it great cash flow for either STR or LTR & it a fun, quaint area that draws a lot of tourism. Don Yerks was my lender for my Gulfport property search & Troy Nowak of Mangrove Bay Realty was my realtor.
For context, I am from Pensacola, FL so I knew very little of the Tampa Bay area and where to invest. The advice I received from both Troy & Don has been invaluable & I will use them again for the next purchase!
I would consider selling my STR since my property is valued under $500K as you mentioned. Feel free to DM me if you are interested.