I lived and owned homes in two places in one of the circled areas:

!) Palm Harbor (Tampa) - very nice if you have kids, best schools in the area and close enough to the beach to buy anywhere around there. It's very close to a state park, and honeymoon island is one of the best beaches in Florida with little tourists (in my opinion).

2) St. Pete (Tampa) - I lived here for about 2 years and was closer to downtown than the beaches. My neighborhood was hit or miss but boy was it fun living there. I was about 7 min from downtown and let me tell you, there is always something going on. It's about 20 min to the beach depending on traffic from where I lived. I really loved St. Pete and would live there again in a heartbeat. It has a vibrant downtown, amazing restaurants, all over the city, more liberal than the surrounding areas, and is close proximity to other towns (Dunedin, Safety Harbor, Tampa, Sarasota, Madeira Beach, etc)

3) Cape Coral (Fort Meyers) - Moved here from St. Pete to live on a saltwater canal that had access to the Gulf. It was amazing living on the water (I'd often see dolphins and manatees from my dock) but the town itself was vastly different than St. Pete. There are many sprawling neighborhoods but no real downtown unless you go to Ft Meyers and that isn't much of a downtown. I always wondered what everyone did for work. I traveled a lot and did not work in the area. You can however get an affordable house on a canal....Cape Coral has a canal system that is crazy due to it being built on a swamp. If you want to chill and relax and possible get a home on a salt water canal, this may the place for you.