Southernmost Point Monument
Key West is the southernmost settlement in the U.S. It is at the end of the Florida Keys, which stretch out into the Gulf Of Mexico like a chain of islands. These are coral islands. The Keys have been, since the 1500s, home to settlers, explorers and many pirates. The jumping off point on a drive to the Keys is usually Miami. The main Islands in the Keys are Key Largo or Long Island, Islamorade, Marathon Key, Big Pine Key and of course Key West. The total length of the Overseas Highway which jumps from island to island in the Keys is 110 miles. Locations along the highway are identified my Mile Markers (or MM in directions). Key West, with population 28,000, is the main attraction for most visitors with dogs and is very dog-friendly. It is at the southern end of the highway.
Key West Aquarium
There are pet-friendly hotels all along the Overseas Highway. Most of these are destination type resorts and not roadside stops for the night. Key Largo has the most pet-friendly lodging except for Key West. There are also vacation rentals on most islands in the Keys. There are dog-friendly restaurants with dog-friendly patios on Key Largo and Islamorada. The Key Largo Conch House in Key Largo offers an outdoor patio. If you plan on staying in the Keys there are a number of dog-friendly activities including charter fishing. Dogs are allowed at the Theatre of the Sea marine animal park except that they may not go near the parrots or the Parrot Theater. You may also take your dog into the National Key Deer Refuge but please keep pets on a tight leash and away from the water as there are many alligators here. If you want to learn about the natural flora and fauna of the Keys then we recommend the Jack Watson's Nature Trail in Big Pine Key. In general, leashed dogs are allowed in Florida State Parks on the Keys but a short leash is greatly recommended due to alligators.
If Key West is your destination then you will find a very dog-friendly environment on your arrival. There are dog-friendly hotels as well as B&Bs and vacation rentals. Larger hotels include the Sheraton Suites Key West, Key West Bayside Inn & Suites and Pelican Landing Resort & Marina. Casa Marina is a Waldorf-Astoria resort but only dogs up to 25 pounds are allowed there. B&Bs include the Francis Street Bottle Inn and Chelsea House.
There are many things to do in Key West with a dog. The Key West Aquarium is the only dog-friendly aquarium that we are aware of in the country. You may bring your leashed dog inside with you. You can walk around the shops and carts at Mallory Square, take pictures at the Southernmost Point Monument and shop at many of the stores on Duval Street. There are boat charters that will take your dog along as well. Your leashed dog can walk the Key West Tropical Forest & Garden a tropical arboretum.
There are many dog-friendly restaurants in Key West. Due to the warm year-round climate a lot of restaurants in Key West are really only "outdoor" restaurants and thus dogs are allowed to join you at many of them. The Cheeseburger Restaurant at 217 Duval Street has a doggie menu as well. Hurricane Joe's Seafood is a popular stop as is Bo's Fish Wagon. There are many other dog-friendly patios so finding excellent dog-friendly dining is not difficult.
The only dog-friendly beach in Key West is Dog Beach at Vernon Avenue and Waddell Avenue. There is one off-leash dog park named Higgs Beach Dog Park at White Street and Atlantic Blvd. This is a fully fenced dog park. Your dog is allowed on leash throughout Dry Tortugas National Park. The catch is that it is an Island 70 miles west of Key West in the Gulf of Mexico and dogs are not allowed on the ferry that takes you there. However, if you arrive via private boat, air charter or boat charter your dog can explore the park with you.
There are many campgrounds and RV parks on the Overseas Highway. At Key West there is the Bluewater Key RV Resort and Boyd's Key West Campground. Sugarloaf Key has a KOA, there are multiple other campgrounds on the Keys.