I greatly prefer the Gulf side of Florida myself...
I second the locations Juli mentioned as well, especially Sand Key. I looked into a condo there myself, but I wanted to live someplace more walkable. You need a car or a bike to get around in most of the coastal towns just South of Clearwater Beach (Sand Key, Belleair, Indian Rocks, Redington, Madeira). It's because of the shape of the island - very long and very narrow. You'll also have to go onto the mainland to get things like major groceries, etc.
I'd also recommend smaller towns North of Clearwater Beach like Dunedin and Tarpon Springs. I'd avoid Clearwater Beach, though, as it's the most popular tourist beach in this area and most of the locals avoid it, too.
Dunedin is a great town and they have only low and midise condos on the Gulf. The beaches are clean and rarely busy. I used to live in Dunedin and would go out to Honeymoon Island and because there are so few people, I'd feel like it was my own private beach.
The Tampa area is definitely more expensive than some other markets in Florida, but it's also extremely popular and most locations you'll be able to rent when you're not here. Places like Ft. Myers will likely give you the same results as far as rental options, too. I also love the beaches around Sarasota, but I'm not as familiar with their real estate market. Anna Maria Island is one of my favorite places in Florida and I like to drive down there just to get away. It gets EXTREMELY busy during the Winter, though, as do most places here on the Gulf Coast.
The Island communities will become overrun with snow birds and tourists from about October-April. This also greatly impacts the surrounding mainland cities and traffic becomes a bit insane. This may not matter as much to you, but it drives me bonkers. lol
The further South into Florida you go, the worse the weather will be in the Summer months. I, personally, wouldn't live much further South than where I am (Clearwater) for that reason, but plenty of people do.
I think it comes down to your personal lifestyle and the things you like to do on a day-to-day basis and what you'd like to do with the property when you're not here. You will find something that suits you, though. There is something for everyone here.