Having lived in Pinellas County for nearly thirty years, your best bets as said before will be on or near the beach, anywhere from Clearwater Beach down to Treasure Island. Actually, you could go down to St. Pete Beach and Pass-a-Grille and do well, but you did specify Largo or Clearwater, and Treasure Island is still relatively close. The Treasure Island Yacht Club and Pasadena Yacht and Tennis Club occasionally have people selling condos at good prices, and obviously, the amenities mean that renting such condos is easier than those without such amenities.
Complexes for those over 55 years in age is a selling point for some, and a complete turn-off for others, so it all depends upon your own age, point of view and lifestyle. 55-and-over communities tend to be safer and quieter, but also tend to have stricter requirements for renters, and the condo association fees and restrictions can be onerous, so do your homework to make sure that they meet your requirements before you purchase. A couple of nice 55+ communities not on the beach, but still in demand, include Top of the World in Clearwater, and either Five Towns or Seminole Garden Apartments in Seminole (next to Largo).
Shipwatch in Largo, right across the Intercoastal Waterway from Indian Rocks Beach, is another very nice choice. Keep in mind, however, that property insurance will be considerably higher for condos on the water, and there is a large selection of condo communities throughout Pinellas County that offer really nice amenities, and none are more than fifteen to twenty minutes from the area beaches.
I thought you might appreciate the opinion of someone who is NOT a real estate agent or broker. Good luck with your property search. ;-)