There are quite a few VRBO properties on Casey Key, as well as Siesta Key. My sense is that Siesta is more condo, while Casey has more freestanding homes. The Sarasota/Bradenton/Osprey/Nokomis area has a lot to recommend, not to mention you can fly in and out of Tampa, Sarasota/Bradenton, Ft. Myers, and maybe Venice. For restaurants and watering holes, it will be mainland, not either Siesta or Casey Keys, although the mainland is not far at all.