We have 24 municipalities in Pinellas County, plus the unincorporated areas. Each one has its own flavor and price points.
Rather than run them all down, it's easier to discuss your target price point and style.
The big rule here is Don't Chase Paper. There are plenty of good money-making options, but not all will be a good fit for you.
For example, you can get into a beach condo-tel (with tons of additional complexity) for $400k-ish in the more "happening" areas. You won't retire on that income stream, but you'll probably break even or slightly better, and you'll have a beach property you can visit a couple of times a year.
Or you can get an SFH/Duplex in a different beach community and make a solid profit, and still have a place to stay on the regular. It's less "sexy" than a beachfront condo-tel, but it's a much better option in my book.
Or you can be inland a bit where there is far less demand (naturally), but draws for small-town events can make up for it (Dunedin has the Highland Games - bagpipes, caber tossing, and haggis).
The Dunedin Causeway is beautiful, but it pales in comparison to what we locals consider an actual beach.
On the other hand, Clearwater Beach just to the south is in high-demand (with the price points to match), but we locals would never go there. Touristy, no parking, traffic is insane, and it's just an "okay" beach by our standards.
I usually recommend finding a lifestyle point that you enjoy. Outdoors (kayaking, fishing, etc.) has plenty of solid options. If you're into trains, we have that covered. If you like museums, we have a ton. Private pilot? We have homes near small airports for layovers.
That way, you can easily connect with and communicate to (market) a customer base you already understand. It makes the transition much easier, and you'll actually enjoy the process.
You can easily focus on one area and become an expert on the local STR scenarios.
But there is all the difference in the world between STR in Indian Rocks Beach (extremely friendly) and neighboring Belleair Beach (totally banned). Knowing how and where you want to be will help you avoid the inevitable rabbit holes that do nothing but waste your time and bandwidth.