Little Gasparilla Island or Similar
 

We are looking for a quiet vacation spot to go to this October where we can kayak, fish, rent a boat, snorkel, relax on the beach etc. We usually go to Siesta Key, but would like to try something new. Has anyone been to Little Gasparilla Island that could give us feed back? Or suggestions for anything similar? We don't need much for nightlife, just a nice sandy beach. We would prefer to rent a house rather than hotel/condo. Thanks in advance for any help!

I've been there to look at real estate, not for vacation. There is no bridge (you take a water taxi), no restaurants, and no stores. For better beaches you'll want to rent a house on the Gulf side.

You just described Sanibel. It's quiet, nice beaches, the best shelling around and you can drive there. Lots of nice condos and October would be quiet.