Lol, you know that Florida isn’t a city, right? The spread on the places you list is approximately an 8 hour drive by car.

That at being said, if all you’re going to do is lay by the pool (a terrible shame, given the natural and man made resources of the state), I would go with the easiest path, which is the Key Biscayne property. And, while late October is a great time for outdoor activities in North and Central Florida, if you are just looking for warm sun it will not hurt to be as far south as you can be.