Key West.

Key West's chain hotels are concentrated on the Atlantic side and at the cruise terminal. Old Town is where the independent guest-house scene thrives — clapboard Victorians and Bahamian conch houses converted to small inns. The Marquesa Hotel, Ambrosia Key West, the Mermaid & the Alligator, Heron House, the Gardens Hotel. Most are twelve to thirty rooms.

What this looks like

Key West is the southernmost incorporated town in the continental U.S. — four square miles at the end of the 113-mile Overseas Highway from Miami. Old Town is the western half of the island: Duval Street as the touristed spine, Whitehead and Simonton as the quieter parallels, Eaton and Truman as the cross-streets where most of the historic guest houses sit. The architecture is uniquely Caribbean — clapboard Victorian, Bahamian conch (steeply pitched roofs, wraparound porches), and the occasional 1840s Greek Revival "eyebrow" house. New Town and the Atlantic side beyond White Street is where the larger resorts and chains sit. The independents we list are almost entirely in Old Town, walking distance to Mallory Square and the sunset celebration.

The standouts

• The Marquesa Hotel — four 1880s Bahamian-style cottages around a courtyard pool, twenty-seven adults-only rooms.
• The Gardens Hotel — an 1875 Bahamian-style estate on a one-acre tropical garden, seventeen adults-only rooms.
• Ambrosia Key West — a 1.5-acre tropical garden compound, twenty-three adults-only rooms, two pools, gay-friendly.
• Heron House — four restored Conch houses, twenty-three adults-only rooms, three pools.
• The Mermaid & The Alligator — an 1904 Queen Anne mansion, nine adults-only rooms, walking distance to Duval.

When to come / who it's for

Two clear windows. Mid-December through April is high season — temperate seventies and eighties, lowest humidity, the regional events (Key West Literary Seminar in mid-January, Hemingway Days in mid-July as the off-peak counterweight). Late April through early June is the shoulder — still warm, lower rates, fewer cruise ships. Hurricane season runs June through November with peak risk August-October; rates drop hard but the weather is genuinely a coin-flip and Key West has been hit. Summer is hot and humid (mid-eighties at night) but the diving and the Marquesa have their loyalists. The region rewards three to five nights — long enough for Mallory Square sunset, a Dry Tortugas day-trip, a snorkeling charter, a Bahama Village wander, and a Cuban-coffee morning at Sandy's. Almost all the independent guest houses are adults-only — this is not the family-vacation region. Couples and friend trips.

Nearby / what else

The Hemingway House on Whitehead. The Truman Little White House. Mallory Square at sunset for the regional ritual. The Southernmost Point buoy (touristed but real). Fort Zachary Taylor State Park for the best swimming beach on the island. The Dry Tortugas — a three-hour boat or a 45-minute seaplane to Fort Jefferson and the snorkeling. Bahama Village for the older Cuban-Bahamian neighborhood and Blue Heaven for breakfast. For dinner: Latitudes on Sunset Key, Louie's Backyard, Santiago's Bodega, El Siboney for old-school Cuban. For a drink: the Green Parrot, Captain Tony's, Sloppy Joe's if you must.