What is the best area to stay in Key West for the first time?

Old Town, on the southern side of Duval Street below Truman Avenue. That puts the Hemingway house, the Southernmost Point, the lighthouse and the restaurants within a short walk, and Mallory Square for sunset about ten minutes away, while keeping you clear of the bars at the north end that run until two. Most of what is available there is restored conch houses turned into small guesthouses with courtyard pools. Book well ahead, because there are far fewer rooms than there is demand.

Should you stay on Duval Street?

Only if the bars are the point of the trip, and even then pick your end. The northern blocks near Mallory Square have open-fronted bars with live music that carries into the street until around closing, so a street-facing room there will not be quiet at any hour you want to sleep. The southern end of Duval, below Truman, is residential and calm. The usual advice is to stay one or two streets off Duval, which costs less, is much quieter, and adds two minutes to the walk.

Is Key West expensive?

Yes, it is one of the more expensive places to sleep in the United States, and the reason is simple: a small island with limited land, no room to build and steady year-round demand. Old Town guesthouses are the priciest, Bahama Village is cheaper for the same walkability, and New Town and Stock Island cost a fraction but commit you to a bike or a car. High season runs roughly December to April, with spring break and Fantasy Fest in late October as separate spikes. Late summer is cheapest and is also hurricane season.

Do you need a car in Key West?

No, and it is usually a liability. The island is four miles by two, Old Town is walkable end to end in about twenty minutes, and almost everyone gets around by bicycle or scooter. Parking in Old Town is scarce, metered, tightly enforced and charged nightly by most hotels on top of the room. If you drive down from Miami, book somewhere with included parking and then leave the car there. If you are staying in New Town or on Stock Island, a bike will still serve you better than the car most days.

Where should you stay in Key West with family?

Truman Annex or the south shore around Casa Marina. Truman Annex is quiet, has wide safe streets and sits next to Fort Zachary Taylor, which has the best swimming on the island. The south shore resorts have pools, private beach areas and space, which matters with younger children. Both are a walkable distance from Old Town without being in the middle of it. One thing to check carefully: a large share of Old Town guesthouses are adults-only, and they do not always say so prominently.

How many days do you need in Key West?

Three nights is right for most people. That gives you a day for Old Town and the Hemingway house, a day on the water for snorkelling or the Dry Tortugas, and a day to swim at Fort Zachary Taylor and do very little. Two nights works if you are driving down the Keys and stopping elsewhere on the way. Longer than four and most people run out of things to do, unless the point is fishing, diving or simply sitting still, which is a perfectly good reason to come.

Which end of Duval Street is quieter?

The southern end, towards the Atlantic and the Southernmost Point. Duval runs the full width of the island from the Gulf side to the Atlantic side, and it changes character as it goes: the northern blocks near Mallory Square and the cruise pier are bars, souvenir shops and live music, while the southern blocks below Truman Avenue turn residential, with guesthouses and quiet streets. Same street, same address line, completely different night.

Where to stayUnited States2026

Where to Stay in Key West

Top pick for first-timers: Old Town

Photo: Julian Lupyan · CC0

Key West is four miles by two and almost all of what you came for sits in Old Town, so the decision is smaller than it looks. It comes down to one street. Duval runs the width of the island, the northern end is loud until two in the morning and the southern end is quiet by ten, and which end you sleep near shapes the whole trip more than the hotel does.

Emma - Hotels and neighbourhoods

Published July 27, 2026

Updated 27 July 2026

In Brief

Where should you stay in Key West?

Stay in Old Town for a first visit, ideally a block or two off the southern half of Duval Street. You get the conch houses, the restaurants and the sunset at Mallory Square on foot, without sleeping over the bars at the north end. Truman Annex is the calm upmarket option, Bahama Village is the best value inside Old Town, and New Town is where the cheap rooms are if you accept driving or cycling in.

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Key West neighborhoods at a glance

The best areas to stay in Key West, compared for vibe, price and who each suits.

Area	Best for	Price	In a word
Old Town (south of Truman)	first timers, romance	$$$	Conch houses, porches and a quiet walk home
Duval Street north and Mallory Square	nightlife, first timers	$$$	Bars, cruise crowds and the sunset celebration
Bahama Village	budget, food	$$	The old Bahamian quarter, and the best value in Old Town
Truman Annex	luxury, families	$$$	The calmest corner, and the island's best beach
Casa Marina and the south shore	families, luxury	$$$	The Atlantic side, resorts and actual sand
New Town	budget, families	$$	Chain hotels, real prices, and you will need wheels
Stock Island	budget, food	$	One bridge out, marinas and the lowest prices

Best areas to stay in Key West

Ranked best-first, with the vibe, who it suits and an honest catch for each. Tap a filter to match an area to your trip.

Find your area - what matters most?

Old Town (south of Truman)
Conch houses, porches and a quiet walk home
$$$ · High-end
First-timersRomanceSightseeing
The residential half of the historic district, below Truman Avenue, where the wooden conch houses have tin roofs, deep porches and white picket fences. The Hemingway house, the Southernmost Point and the lighthouse are here, and the guesthouses are mostly restored homes with courtyard pools.
Good to know: The best compromise on the island: five to fifteen minutes' walk to everything, and genuinely quiet at night. Most of the stock is small guesthouses rather than hotels, many of them adults-only, so check that if you are travelling with children. Book early, because there are not many rooms.
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Duval Street north and Mallory Square
Bars, cruise crowds and the sunset celebration
$$$ · High-end
NightlifeFirst-timersShopping
The commercial upper end of the island, running from the harbour down a few blocks of open-fronted bars, T-shirt shops and live music. Mallory Square holds the sunset celebration every evening with street performers, and the cruise pier is right beside it.
Good to know: The loudest place to sleep in Key West by a wide margin, with live music from open-fronted bars until around two. It is also busiest in the middle of the day when ships are in. Stay here on purpose if the bars are the trip, and ask for a courtyard-facing room even then.
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Bahama Village
The old Bahamian quarter, and the best value in Old Town
$$ · Mid-range
BudgetFood & wineFirst-timers
The blocks west of Duval around Petronia Street, settled by Bahamian immigrants and still the most distinct part of the island, with brightly painted cottages, roosters in the road and a handful of very good Caribbean kitchens.
Good to know: Inside Old Town and a few minutes from Duval, but priced noticeably below it, which makes it the value pick for anyone who wants to walk everywhere. The area is quiet and residential, and quieter still on the western edges. Fewer hotels, more guesthouses and rentals.
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Truman Annex
The calmest corner, and the island's best beach
$$$ · High-end
LuxuryFamiliesRomance
A former naval base on the western tip, redeveloped into wide quiet streets with mature trees and the old Harry S. Truman winter White House at its centre. Fort Zachary Taylor state park sits at the end of it, with the clearest water and the best swimming on the island.
Good to know: Peaceful to the point of being sleepy, and still only about ten minutes' walk to Duval. The trade-off is that there is nothing to walk out to in the evening. Fort Zachary Taylor charges park entry and the beach is coarse rock and coral rather than sand, so bring water shoes.
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Casa Marina and the south shore
The Atlantic side, resorts and actual sand
$$$ · High-end
FamiliesLuxuryRomance
The stretch along the southern Atlantic shore below Old Town, where the larger resort hotels sit with private beaches, pools and loungers. Higgs Beach is here, and Smathers, the longest beach on the island, runs east from it.
Good to know: The only part of Key West that feels like a beach holiday, which is the appeal and also the warning: Key West beaches are man-made, shallow and full of seaweed compared with the rest of Florida. Nobody comes here for the sand. About fifteen to twenty minutes' walk to Duval.
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New Town
Chain hotels, real prices, and you will need wheels
$$ · Mid-range
BudgetFamilies
The eastern half of the island past the golf course, laid out in the twentieth century with strip malls, supermarkets and the airport. This is where the chain hotels and motels are, and where most people who live on the island actually live.
Good to know: Rooms cost a fraction of Old Town and there is no charm whatsoever. It is around three to four miles to Duval, which is a short drive, a cheap bus or a very pleasant twenty-minute bike ride. Sensible for families and longer stays, poor for a two-night trip.
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Stock Island
One bridge out, marinas and the lowest prices
$ · Budget
BudgetFood & wine
The next island north, historically the working end of Key West with the boatyards, the fishing fleet and the commercial marinas. Two marina resorts have opened here and there are good, cheap, genuinely local seafood places along the docks.
Good to know: The cheapest beds within reach of Key West and about a ten-minute drive from Duval, so you are committed to a car, a bike or the bus for everything. Still scruffy in parts. Worth it in high season when Old Town prices become hard to justify.
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Where not to stay in Key West

Key West is a small, safe and heavily policed tourist island, and there is nowhere here you need to rule out for safety. The mistakes are about money and noise. The most common is booking on the northern blocks of Duval and then discovering that open-fronted bars with live music do not close until around two, every night, all year. The second is paying Old Town rates for a hotel in New Town because the address still says Key West, when it is three or four miles from anything you came to see. The third is renting a car at all: parking in Old Town is scarce, expensive and enforced hard, and most hotels charge separately for it. The fourth is arriving during Fantasy Fest in late October without knowing what it is, which is an adults-oriented street festival that fills the island and roughly doubles rates. And be honest with yourself about beaches, because Key West has very little sand and people who came for a beach holiday are regularly disappointed.

Getting around Key West

Key West International is on the eastern side of the island, about ten minutes from Old Town, with connections mostly through Miami and other Florida hubs. Driving down from Miami takes roughly four hours on the Overseas Highway, which is a beautiful drive and a poor reason to keep the car once you arrive. Old Town itself is entirely walkable, about twenty minutes end to end, and the island runs on bicycles and scooters, which every hotel can arrange. There is a cheap local bus and a tourist trolley that loops the sights. Parking is the real problem: Old Town has residential permit zones, metered spaces that fill by mid-morning and hotels that charge nightly for a space. If you are driving down, look for accommodation with included parking or plan to leave the car at the hotel and not touch it.