The location
Islamorada is a village of six islands strung along the Overseas Highway in the Upper Keys, roughly a ninety-minute to two-hour drive south of Miami International Airport and about the same distance north of Key West. It is the stretch of the Keys people mean when they talk about the Sport Fishing Capital of the World.
The Atlantic sits on one side and Florida Bay on the other, which is why the fishing here is unlike anywhere else in the state — offshore, reef and backcountry flats all within reach of the same morning. Tarpon, bonefish, permit, mahi and sailfish are all in season at different points of the year. Alligator Reef and Cheeca Rocks are the local snorkel and dive names worth knowing.
Robbie’s of Islamorada at mile marker 77.5 is the famous tarpon-feeding marina, with boat and kayak rentals attached. Theater of the Sea at mile marker 84.5 is one of the oldest marine mammal parks in the world. Founders Park at mile marker 87 has a beach, water sports and an open-air amphitheatre, and the Morada Way Arts & Cultural District hosts galleries and a monthly art walk.
Anne’s Beach is the shallow, boardwalk-edged stretch locals send you to. Indian Key Historic State Park and Lignumvitae Key Botanical State Park are both reachable only by boat or kayak. Windley Key Fossil Reef Geological State Park is a former quarry cut straight into ancient coral, and the History of Diving Museum is a genuinely good rainy afternoon.
Key Largo and John Pennekamp Coral Reef State Park sit thirty minutes north. Marathon and the Seven Mile Bridge are forty minutes south. Everglades National Park and Key West are both comfortable day trips, which is part of why extended stays here rarely feel confined.
High season in the Florida Keys runs roughly November through April, when the weather is dry and mild and snowbird demand for monthly rentals is heaviest — the best winter homes are usually spoken for months ahead. Summer and early autumn are warmer, quieter and better value, and they are prime months for fishing and diving. Whichever window suits you, our resort homes are built for monthly and seasonal stays rather than weekends.
Reserve your stay
Contact Castaway Vacation Rentals of the Florida Keys directly for availability, rates and personalized assistance.