Key West's housing stock is distinctive, with much of Old Town composed of restored conch-style cottages and Victorian-era frame buildings, many dating to the 1800s and located within the roughly 4,000-acre Key West Historic District. Historic preservation shapes much of the island's character, and the limited land area of the island constrains new development, giving the city an intimate, low-rise scale.

Old Town is Key West's historic core, holding the Key West Historic District and its concentration of late-19th-century wooden architecture, galleries, and the seaport. Beyond the historic district, the rest of the island is home to the city's year-round residential and commercial areas, including waterfront neighborhoods and the Truman Annex, the former naval base grounds that have become a sought-after residential enclave near the heart of the island.

Key West's culture blends Cuban, Bahamian, and American influences, evident in its food, music, and architecture. Mallory Square's nightly sunset celebration draws performers and crowds, while the island's compact, walkable scale and lively arts scene give it a distinctly relaxed, creative character. Tourism anchors the economy, and the island's year-round subtropical climate supports an outdoor-oriented way of life centered on boating, fishing, and time on the water.

Key West is served by the Monroe County School District, whose administrative offices are headquartered in the city and whose schools span the entire Florida Keys from Key West to Key Largo. The district operates public elementary, middle, and high schools across the island chain, serving students throughout the Keys. The College of the Florida Keys, a public community college, operates a campus in Key West, providing local higher-education options for residents and students from across the region.

Key West International Airport offers scheduled flights connecting the island to the mainland, while the Overseas Highway (U.S. Route 1) threads the length of the Keys to Key West, linking it to Miami and the rest of Florida. Intercity buses and shuttle services run from the Miami and Fort Lauderdale airports to the island, and the city itself is compact and walkable with local transit and taxi options.

The waterfront defines recreation in Key West. Mallory Square hosts the famous sunset celebration, and Fort Zachary Taylor Historic State Park combines a pre-Civil War-era fort with a beach and clear-water snorkeling. The Ernest Hemingway Home and Museum and the island's marinas, fishing charters, and watersports reflect a deep connection to the sea, while sailing, diving, and kayaking through the backcountry waters of the Keys round out a life spent outdoors.