We just returned from a vacation to Siesta Key and we got a rental through VRBO. Here are my thoughts. I would not suggest the place we stayed at unless staying in the apartments, and only then if you had a hard time finding a better place. (Casa Blanca). It was fine, but there is SO much to choose from, I don't see why you'd pick it as there is better stuff. On VRBO we noticed some nice rental cottage homes. I would suggest this if you'd like some privacy. No matter where you are on the island you are pretty much within walking distance to the beach depending on who is in your party. If I were to go back, I would pick a condo with a beach view, or go with a place on the canal, with preference to the canal. I like the overgrowth of vegetation on the canal. Another place I would suggest if you can find something reasonable is Casey Key.
There are few places to eat on the island, though Sarasota has plenty to offer at a close distance. There is a good breakfast place, the Sun Garden Cafe, and Curt's offers the general fish fare. But the nice thing about a condo or rental is having the flexibility of cooking. There is a Publix just accross the bridge.
