I am not that familiar with the area, however after doing some market research I see the Fort Walton Beach/Destin area as a good one to start. 

@Drake EspenlaubAs noted, your 401(k) is stuck in your employer plan until you change jobs or reach age 59 1/2 while still employed with the company sponsoring the 401(k).If you have both tax-deferred (Traditional) holdings and Roth holdings in your plan, they may or may not have differing rollover destinations. 

Do you have any specific destinations in either country you are looking at?

It's not the destination, because you will get there.

@David Stebner I manage my own vacation rentals in Fort Walton Beach/Destin, FL and also manage a number of properties for others.

Toward the bottom of the list you'll find lower cap rates along with favorable elements like skilled job growth, built-in scarcity and lifestyle destinations.

I totally agree - Costa Rica is my next destination for these reasons alone.

(no coffee shop though) but most destinations involve getting in a car.

As an added bonus, they get to travel to a wonderful destination  every year to check on their rentals!  

Santa Rosa Beach (or 30A) is a very sought after, very upscale destination on the panhandle.