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Where to stay in the Florida Keys: small inns and guesthouses from Key Largo to Key West

The Overseas Highway links the Keys island to island, from Key Largo down to Key West. Each stretch has its own feel, and small inns, cottages and guesthouses are a big part of the charm.

Key Largo

Key Largo is the closest stretch to the mainland. John Pennekamp Coral Reef State Park, the first undersea park in the US, offers snorkeling, diving, glass-bottom boat tours and kayaking, and its reef trips can take you to the underwater Christ of the Deep statue.

Islamorada

Islamorada calls itself the Sport Fishing Capital of the World, and backcountry and offshore charters are easy to find. At Robbie's, at mile marker 77.5, you can hand-feed tarpon from the dock. The History of Diving Museum, at mile marker 83, tells the story of diving and underwater exploration.

Marathon

Marathon sits in the middle of the Keys. The Turtle Hospital runs guided tours of its sea turtle rescue and rehabilitation center. The Old Seven Mile Bridge reopened in 2022 as a 2.2-mile walking and cycling route to Pigeon Key, a historic island with a small museum (admission is charged on the island).

The Lower Keys

The Lower Keys are quieter. Bahia Honda State Park, on Bahia Honda Key, is known for its beaches. The National Key Deer Refuge on Big Pine Key protects the endangered Key deer, the smallest subspecies of white-tailed deer, found nowhere else in the world. Early morning and dusk are the best times to see them.

Key West

Old Town Key West has many historic houses run as guesthouses and B&Bs. The Sunset Celebration at Mallory Square happens every evening, and the Ernest Hemingway Home and Museum is nearby. Dry Tortugas National Park is a day trip by ferry or seaplane from Key West; book ahead, and check for service changes.

Tips for booking a small Keys property

  • Check minimum stays, especially in peak season and over holidays.
  • Ask about parking, which can be tight in Old Town Key West.
  • Check whether the property is adults-only, since some Key West guesthouses are.
  • Atlantic hurricane season runs from June 1 to November 30, so read the cancellation terms.

Plan your stay

Ask ChatGPT or another AI assistant for a small inn in the area, or search bookd.direct, where independent properties list directly and you pay the property.

Also see: Where to stay on Florida's Gulf Coast

Details checked against public sources in October 2026. Opening times, prices and closures change, so check with each place before you travel.