Where to stay in Key West, and the license to check before you pay

Where you sleep in Key West decides whether your evenings are a walk or a ride. Pick the area first. Six of them are below, each with what it trades and, where Booking.com keeps a list for it, that list at the top of this page. If it is a vacation rental, run the license check before any money moves.

The areas

Old Town

The part you came for: the Duval Street end, the guesthouses, the cemetery, the Hemingway house and the sunset at Mallory Square. Staying here means walking to nearly everything, and it means a car becomes a liability rather than an asset. It is also louder, and the closer you are to Duval the more that matters. Booking.com calls it Downtown Key West, and its list for it is Old Town’s guesthouses, inns and hotels.

The Historic Seaport

Old Town’s harbor, at Key West Bight. The Dry Tortugas ferry leaves from the terminal at 100 Grinnell Street, and so do a good share of the day’s boats: Honest Eco’s dolphin and sunset sail, the Sunset Watersports parasail at 201 William Street and the FishMonster party boat at A&B Marina, 700 Front Street. If the trip is built around an early boat, this is the corner to sleep in, and the hotels near the ferry are timed on foot to the terminal door. Booking.com has no list of its own for the Seaport; those four hotels are the closest we card.

The Truman Annex

The west end of Old Town, on the old naval station grounds around the Truman Little White House at 111 Front Street, with Fort Zachary Taylor’s beach at its far end. Much of it is a gated neighborhood of private homes, and about 300 of them held special short-term rental licenses under a 20-year settlement with the city. Those licenses ended on 22 December 2025, and owners in one section have taken the city to court over it. Until that changes, a home in the Annex rents by the month, and a listing offering a long weekend there is exactly what the city’s warning below is about. Booking.com has no list that keeps to the Annex.

Casa Marina and the south shore

The Atlantic side of the island, where Higgs Beach sits beside the historic Casa Marina. It is a flat bike ride to Duval and has the island’s best family beach on the doorstep: two playgrounds, restrooms and a restaurant, open 6 a.m. to 11 p.m. It is not a ferry-morning walk, though: the Casa Marina is 1.4 miles from the Dry Tortugas terminal, about 29 minutes on foot. The Casa Marina is the one hotel this page names, in the places to stay at the top.

New Town

Toward the airport: newer, quieter, chain hotels, and parking that is not a daily negotiation, and the stop for the Greyhound from Miami is in front of the airport terminal; how to get to Key West has the flights, the bus and the ferry. Smathers Beach is on this side, across South Roosevelt from the runway. The trade is that you are commuting into Old Town every day. Booking.com’s list near the airport prints each place’s distance from it, and not all of them are in New Town, so read the distance before you book.

Stock Island

The next island east, off Key West altogether, and inside the city’s on-demand bus zone (“one zone in Key West, including Stock Island”), so you are not stranded there without a car. Booking.com’s Stock Island page lists Key West’s hotels rather than Stock Island’s, so there is no list for it here.

The honest framing is that Key West is small enough that you do not need a car at all, and the neighborhood decision is mostly a decision about whether you want to walk home at midnight or ride.

When matters more than where

A few things move the experience more than your choice of street:

• Hurricane season. It changes prices and it changes cancellation terms. What the season actually means here is worth reading before you book a non-refundable rate.
• Cruise ship days. Old Town fills and empties on a schedule that has nothing to do with your hotel.
• Christmas and New Year’s. The New Year’s Eve drops are on Duval and at the Seaport, a walk from Old Town; the holiday page has the dates and the night’s transport.
• January to March. The festivals and the spring breaks fill the island week by week, and the last week of January carries two festivals at once; the January-to-March page has the dates.
• The Dry Tortugas ferry. It checks in at 7 a.m. at 100 Grinnell Street, so the night before it is the one night when the street does matter: hotels within a walk of the terminal.

What decides it

Pick the area for the evenings you want: walk home from Duval in Old Town, wake by the boats at the Seaport, keep the beach close on the south shore, or park easily in New Town. Then, for a rental, check the license before any money moves. The building is your call.