The town of Surfside, home to my parents, is a tiny town nestled between Miami Beach and Bal Harbour. You get a lot of the benefits of Bal Harbour at about half the price. The town starts at 88th St. and ends at 96th, just before the ritzy Bal Harbour Shops. On Harding, an inconveniently designated one-way street, you will find a pretty charming "Main Street". There are florists, a Flannigan's, a Publix (though that one kind of sux), a tailor, some banks, and several good restaurants. There's ample parking west of Harding, plus a bunch of metered spots on Harding itself.
A place of which you likely have not heard is Bianca's Gourmet Shop. It's a wonderful little sandwich place owned by friends of my girlfriend's friend of the family (but not her dog's previous owner's cousin or anything).
Their BBQ Steak Ciabatta might just be the most delicious sandwich I have ever eaten. It has feta cheese, caramelized onions and guacamole on top of tender slices of beef that are surprisingly easy to chew. Anyone who has ever eaten a steak sandwich knows why I am pointing that out.
My brother Brendan is a skeptic, but next time he is visiting from the Left Coast, I shall enlighten him. Maybe we'll do Bianca sandwiches at the pool rather than our traditional medianoches.