Key West

Casa Marina Key West, Curio Collection by Hilton

Casa Marina District / South Shore

The 1920s railroad-era grand dame on the island's longest private beach — 1,100 feet of sand, two oceanfront pools, a restored Mediterranean Revival lobby, and a quiet south-shore address twenty minutes' walk from Duval.

Ocean Key Resort and Spa

Mallory Square / Top of Duval

Zero Duval Street — the very top of the island's main street, beside Mallory Square, with balconies over the harbor, the Sunset Pier's nightly live music, and a freshly renovated lobby, pool lounge, and spa.

Pier House Resort and Spa

Mallory Square / Top of Duval

The rare Old Town hotel with its own beach — a private strip of white sand at the foot of Duval, the legendary Chart Room bar where Jimmy Buffett played early gigs, a Caribbean spa, and sunset from the pier.

The Marker Key West Harbor Resort

Historic Seaport

The modern harbor resort on the Historic Seaport — 96 balconied rooms, three pools including an adults-only one, and the sunset-sail docks and seafood restaurants of the harborwalk at the door. Three blocks to Duval.

The Gardens Hotel

Old Town / Mid-Duval

Nineteen rooms hidden in a lush botanical garden a block off Duval — two heated pools with a cocktail bar, a wine gallery, breakfast served on the porches, and a calm that feels miles from the crowds.

Southernmost Beach Resort

South Duval / Atlantic Shore

The big, easygoing beach resort at the Atlantic end of Duval — three heated pools, a private sandy beach and sun pier, a beach cafe with ocean views, and the Southernmost Point buoy a block away.

The Perry Hotel and Marina Key West

Stock Island

A modern marina hotel on Stock Island, the working-waterfront key next door — two pools, a 288-slip harbor, dockside restaurants, dog-friendly rooms, and better rates than Old Town, a short drive from Duval.

La Concha Key West, Autograph Collection

Old Town / Mid-Duval

The Grand Dame of Key West — a pink 1926 landmark in the middle of Duval Street, freshly renovated as a Marriott Autograph Collection hotel and celebrating its hundredth year with a heated pool, rooftop sunset terrace and Cuban-inspired cafes.

The Reach Key West, Curio Collection by Hilton

Atlantic Side / South Old Town

An oceanfront resort on one of Key West's only natural sand beaches, at the quiet Atlantic end of Simonton Street — pool, beach rentals, oceanfront dining and Casa Marina's amenities a short stroll away.

Hyatt Centric Key West Resort and Spa

Old Town / Harborfront

A waterfront resort at the harbor end of Old Town, steps from Mallory Square — two small private beaches, a heated pool, a full spa, its own marina and a Richard Blais restaurant on the water.

Opal Key Resort and Marina

Old Town / Mallory Square

The former Margaritaville resort next to Mallory Square, reborn as Opal Key — 178 balconied rooms, a central pool with free afternoon frozen drinks, a 37-slip marina and the Sunset Key launch at the door.

Sunset Key Cottages

Sunset Key (private island)

Key West's private-island splurge — one- to four-bedroom cottages with verandas, kitchens and ocean views on a 27-acre island about 500 yards off Mallory Square, reached only by the resort launch.

Fairfield Inn and Suites Key West at The Keys Collection

New Town / North Roosevelt Boulevard

A dependable, family-friendly value pick in New Town — resort-style pool with cabanas, free hot breakfast and free parking, a rare combination in Key West, with a downtown shuttle option to Duval.

Eden House

Old Town / Fleming Street

A laid-back, long-running Old Town guesthouse on Fleming Street — courtyard pool and hot tub under the palms, koi ponds and hammocks, a free daily happy hour and free parking, at a fraction of Duval resort prices.

Seashell Motel and Key West Hostel

Old Town / Atlantic Side

The cheapest bed in Old Town that is not a compromise on location — private motel rooms and shared dorms on South Street, a short walk from the Southernmost Point, South Beach and the Atlantic end of Duval.

Sunset Celebration at Mallory Square

The nightly island ritual — fire jugglers, tightrope walkers, cat-and-dog acts, conch fritters, and a waterfront crowd that applauds when the sun drops into the Gulf. Free, every night, and the one thing nobody skips.

Duval Street

A mile and a quarter from the Gulf to the Atlantic — Sloppy Joe's and Captain Tony's at the harbor end, galleries and cafes in the middle, the quiet Atlantic blocks at the bottom. Walk the whole thing once, sober, then pick your stretch.

Ernest Hemingway Home and Museum

The Spanish Colonial house where Hemingway wrote through the 1930s — his writing studio, the pool that cost his "last cent," and some fifty-odd cats, about half of them six-toed descendants of the legend. Go early, take the guided tour.

Southernmost Point Buoy

The striped concrete buoy that marks the bottom of the continental US — "90 miles to Cuba" — and the island's most-queued photo. The original is behind seawall construction; a full-size twin stands at the foot of Duval.

Dry Tortugas National Park and Fort Jefferson

Seventy miles west by high-speed ferry or seaplane: a vast hexagonal brick fort rising from turquoise water, snorkeling off the moat wall, and one of the most remote national parks in America. The best day trip in Florida.

Key West Lighthouse Museum

Climb 88 steps up the 1848 tower for the best view on the island — tin roofs, Hemingway's garden across the street, the harbor beyond — then tour the keepers' cottage and the story of the woman who kept the light.

Truman Little White House

Harry Truman's winter White House — 175 days of presidential work and poker on a quiet Navy base — seen on an hour-long docent-led tour of the original furnishings, his desk, and the famous poker table.

Fort Zachary Taylor Historic State Park

Key West's best beach and a Civil War fort in one state park — shaded picnic groves under Australian pines, snorkeling off the rocks, a moated brick fort with buried cannons, and a sunset view the locals choose over Mallory.

Key West Butterfly and Nature Conservatory

A glass-domed tropical garden on lower Duval where about a thousand butterflies from 50-plus species land on your shoulders — plus finches, turtles, and Rhett and Scarlett, the resident flamingo pair.

Key West Reef Snorkel Trip

A three-hour catamaran run to two spots on North America's only living coral barrier reef — gear, instruction, flotation vests, and drinks after. The easiest way to see what the Keys are really about.

Conch Tour Train

Key West's orientation lap since 1958 — an open-air, yellow-roofed train looping Old Town for an hour of narrated history, with hop-off privileges for the day. Ride it on day one and the rest of the island makes sense.

Key West Shipwreck Treasure Museum

How Key West got rich off ships wrecked on the reef — costumed storytellers, two floors of salvaged treasure including a Spanish silver bar you can lift, and a 65-foot lookout tower over Mallory Square.

Bahia Honda State Park and the Overseas Highway

The Keys' most beautiful beaches, an hour's drive up the Overseas Highway — soft sand, turquoise shallows, the broken arch of Flagler's old railroad bridge, kayaks, and snorkel boats to Looe Key. The best day trip by car.

Key West Sunset Sail

Watch the famous Key West sunset from the water instead of the crowded pier — a two-hour catamaran sail out of the historic seaport with live music, appetizers and the whole Gulf horizon to yourself.

Key West Aquarium

A Depression-era aquarium on Mallory Square that opened in 1935 — compact, open-air and hands-on, with shark and turtle feedings, a touch tank of conchs and sea stars, and rescued sea turtles you can meet up close.

Mel Fisher Maritime Museum

Gold bars, emeralds and silver coins from the 1622 wreck of the Atocha — plus the sobering story of the slave ship Henrietta Marie — in a nonprofit museum at the corner of Greene and Whitehead.

Audubon House and Tropical Gardens

A restored 1840s sea captain's house on Whitehead Street, furnished in wrecking-era style, hung with John James Audubon's bird engravings and wrapped in a quiet acre of tropical gardens.

Fort East Martello Museum

An unfinished Civil War brick fort by the airport, now a museum of island history, folk art and Key West's most notorious resident — Robert the Doll, who you must ask before photographing.

Key West Museum of Art and History at the Custom House

A red-brick 1891 Romanesque landmark on Front Street where the USS Maine inquiry was held — now two floors of island art and history, a few steps from Mallory Square.

Ghosts and Gravestones Key West

A ninety-minute after-dark ghost tour aboard the Trolley of the Doomed — pirates, plague, the hanging tree at Captain Tony's and the island's crowded old cemeteries, told by a costumed guide.

Key West Historic Seaport and Harborwalk

The old Key West Bight, where turtlers, spongers and shrimpers once unloaded — now a free mile-long harborwalk of schooners, raw bars and dockside music, and the departure point for half the island's boat trips.

Key West Historic Cemetery

Nineteen acres of whitewashed above-ground vaults in the middle of Old Town, where up to 100,000 islanders rest — with the USS Maine sailors, Cuban patriots, chickens on the tombs and the island's wittiest epitaphs.

Smathers Beach

Key West's biggest public beach — about half a mile of palm-lined sand on the Atlantic side, with calm shallow water, volleyball, food trucks, water-sports rentals and one of the few spots on the island for both sunrise and sunset.

Higgs Beach and the African Cemetery Memorial

A local favorite on the Atlantic shore with a pier, playgrounds and shady picnic spots — and, beside the sand, a moving memorial to the Africans rescued from slave ships in 1860 who died and were buried here.

Key West Garden Club at West Martello Tower

A free, volunteer-tended tropical garden growing inside the brick walls and arches of a Civil War fort on the Atlantic shore — one of the most beautiful and least-known corners of Key West.

Key West Tropical Forest and Botanical Garden

Fifteen acres of native hardwood hammock, freshwater ponds and butterfly gardens on Stock Island — the only frost-free botanical garden in the continental U.S., celebrating 90 years, and a top birding stop.

USCGC Ingham Maritime Museum

Climb aboard the most decorated cutter in Coast Guard history — a 1936 ship that sank a U-boat in World War II, served off Vietnam and rescued Cuban refugees, now a National Historic Landmark docked at Truman Waterfront.

Sloppy Joes Bar

The Duval Street saloon that opened the day Prohibition ended in 1933 and became Hemingway's hangout — live music from midday to late, ceiling fans, open windows and the annual Hemingway look-alike contest.