Islamorada (pronounced Eye-Lamorada) are series of islands in the Upper Florida Keys. About an hour and a half drive from Miami, Islamorada has a real island living vibe. There is a fairly active restaurant scene and each year Islamorada hosts to the annual Bay Jam Music Festival in the spring. Islamorada is also known as the sport-fishing nirvana. Obviously, it's surrounded by water so makes the perfect spot for those who enjoy water sports like fishing, boating, snorkeling and diving. In fact, John Pennekamp Coral Reef State Park is nearby and home to the only living barrier reef in North America. However, all this fabulousness comes at a price with median home values being very high.