As the southernmost point in the continental United States and a major tourist destination for both the party-hearty crowd and family sun-lovers, the small island of Key West is rarely considered a place for cheap accommodations. However, exceptions to the norm do exist, with a handful of options in both the New Town and Old Town sections of the colorful “Conch Republic.”
After traversing the 127.5-mile Overseas Highway through the Florida Keys and crossing the last bridge into Key West, the roadway blends into Roosevelt Boulevard, where a couple of affordable hotels are situated. These are in the area known as "New Town," which was developed after the neighborhoods of Bahama Village and the "Old Town" historic district. Along the Gulf of Mexico on North Roosevelt, the Key West Bayside Inn & Suites offers rooms in the mid-price range, which is generally hard to find on the island. On South Roosevelt, the Best Western Key Ambassador Resort is similarly priced with a location near the airport. Both have swimming pools, continental breakfast and free parking. Although the location is a bit removed from the main action of Duval Street, shuttle buses run often between New Town and Old Town.
Key West revolves around proximity to Duval Street, which runs for about a mile through the center of Old Town, famous for all-night parties, pubs and parades, including the October Aquafest celebration where clothing is optional and outrageous is revered. Notoriously expensive hotels line Duval Street and the blocks sprouting off in either direction, but there are some little-known alternatives. The Spindrift Motel, just one block off Duval Street, and the Southwind Motel on Simonton Street put you within walking distance of the action without hijacking your monthly paycheck. Accommodations are modest but adequate for collapsing in bed after full days and fun nights exploring the two- by four-mile island paradise. Both properties have swimming pools, optional kitchenettes and free parking, which is a big plus in Key West.
Known as the home of Key West City Marina and Charter Boat Row, the area of Garrison Bight is an authentic fishing community seemingly removed from the tourist action of Key West. However, it is just blocks from Duval Street and is a major draw in its own right for anglers in pursuit of lobster, marlin, grouper, sailfish and dozens more species inhabiting the waters of the Atlantic Ocean and the Gulf of Mexico. Lodging is sparse in Garrison Bight, but snagging a room at Harborside Motel & Marina just off Highway 1 and Eisenhower Drive gives you an affordable rate in a cultural enclave with deep ties to Key West's history. Located right on the harbor, the motel proves fish-cleaning stations, barbecues and a swimming pool, all just a bike-ride away from beaches, shopping and cruise ships.
The Bahama Village neighborhood is home to Fort Zachary Taylor Beach and dozens of small conch cottages formerly housing the families of cigar factory workers in Key West. Many residents are of Bahamian heritage and some still remember the days of Ernest Hemingway frequenting the small clubs and cafes in the village. Angelina Guest House, a former bordello and gambling house, sits in the heart of Bahama Village, just two blocks from Duval Street. A lagoon-style pool, swaying hammocks and a wraparound white-fenced balcony reflect the architecture and ambiance of what locals call the "Old Florida" lifestyle. The 1848 conch-style Seascape Tropical Inn on Olivia Street offers just six small rooms and one suite, but is closer to the hustle and bustle of tourist activity. A free continental breakfast is served daily beneath the poolside sapodilla tree.
