The Island
Key West is a 2x4-mile island at the end of the Florida Keys — the southernmost city in the continental United States, 90 miles north of Havana. The island sits where the Gulf of Mexico meets the Atlantic Ocean, which produces a climate closer to the Caribbean than to Florida: average temperatures in the upper 70s year-round, consistent trade winds from the southeast, and a flora — bougainvillea, coconut palms, poinciana — that would be frost-killed anywhere else in Florida.
The city has roughly 25,000 permanent residents and an economy built on tourism, commercial fishing, and the federal government (NAS Key West is the island's largest single employer). It has been, at various points in its history, the wealthiest city per capita in the United States (1880s, driven by wrecking — the legal salvage of ships run aground on the reef), a center of cigar manufacturing, a naval base, and a fishing camp that attracted writers and painters. It is now primarily known as a destination.
Old Town and the Conch Houses
Old Town Key West — roughly the western third of the island — contains the largest collection of 19th-century frame vernacular architecture in the United States. The buildings are called conch houses, named after the Keys' original settlers (the Conchs, pronounced "Conks"), and they were built by ship carpenters using techniques adapted from boat-building: lightweight timber frames, wide porches (verandas) to catch trade winds before air conditioning, louvered shutters, and elevated foundations to deal with flooding. The architectural character of Old Town — dense, walkable, shade-covered, with narrow streets and mature tropical trees — is the reason people keep coming back.
The Curry Mansion
Curry Mansion (1869, Caroline Street) was built by William Curry, Key West's first native-born millionaire, whose fortune came from wrecking and ship supply. The mansion is one of the most architecturally significant buildings in Old Town — a three-story Italianate structure with wrap-around porches, a widow's walk, and a collection of architectural details and historical pieces that span the mansion's storied past. It now operates as a guesthouse with 21 guest rooms and a shared heated pool, half a block from Duval Street.
Caroline Street and the James House
Caroline Street is one of the main residential streets of Old Town, running parallel to Duval and containing some of the finest examples of late-Victorian conch house architecture on the island. The James House — one home away from Duval on Caroline — is a historic guesthouse with 8 private rooms, en-suite bathrooms, and private balconies, with access to the Curry Mansion pool across the street for guests.
Duval Street
Duval Street runs the full 1.2-mile length of Key West from the Gulf to the Atlantic — the commercial spine of Old Town. The northern end (Mallory Square, the Gulf) is where the sunset celebration happens every evening; the southern end (South Beach, the Atlantic) is quieter. The street has a reputation earned over decades as a place where the usual social rules are relaxed, which is both its appeal and its limitation, depending on what you're looking for.
The Florida Keys and the Seven Mile Bridge
Key West is at the end of US-1's famous run through the Florida Keys — a 125-mile island-hopping drive from Florida City through Key Largo, Islamorada, Marathon, and the Lower Keys. The [Seven Mile Bridge](https://www.nps.gov/nr/travel/american_latino_heritage/Seven_Mile_Bridge.html) between Marathon and the Lower Keys is the longest bridge on the highway — a two-lane road over open water with views to the horizon in both directions. Marathon, the commercial center of the Middle Keys, sits on the highest concentration of canal-front homes in the Keys and is the primary base for serious saltwater fishing and boating in the chain.
Ernest Hemingway
Ernest Hemingway lived in Key West from 1928 to 1940 — the most productive decade of his career. He wrote A Farewell to Arms, Death in the Afternoon, Green Hills of Africa, and To Have and Have Not (set in Key West) in the Spanish Colonial house at 907 Whitehead Street. The house is now a museum; the cats that live on the grounds are descended from a six-toed cat that Hemingway kept, and the "Hemingway cats" have been a feature of the property since his tenure.
Fishing and the Reef
The [Florida Keys National Marine Sanctuary](https://floridakeys.noaa.gov/) encompasses 2,900 square miles of ocean surrounding the Keys, including the only living coral barrier reef in the continental United States — the third largest in the world. The reef runs 4-7 miles offshore and produces diving and snorkeling conditions that draw visitors from across the Eastern Seaboard. The backcountry (the shallow Gulf flats north and west of the Keys) is one of the premier shallow-water fishing destinations in the world — the combination of clear water, bonefish, tarpon, and permit that defines Keys flats fishing.
When to Go
Key West's peak season is December through April — dry season, lower humidity, temperatures in the mid-70s. Summer (June–September) is hot and humid with afternoon thunderstorms but has the best water visibility for diving and lower accommodation rates. Hurricane season runs June through November; the Keys are evacuated for major storms, and travel insurance is essential for summer bookings.
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Search stays on CielStay →Frequently asked questions
What is the Curry Mansion in Key West?
The Curry Mansion was built in 1869 by William Curry — Key West's first native-born millionaire, whose fortune came from wrecking (the legal salvage of ships run aground on the reef) and ship supply. The three-story Italianate mansion on Caroline Street is one of the most architecturally significant buildings in Old Town Key West, with wrap-around porches, a widow's walk, and a collection of historical pieces from the mansion's storied past. It now operates as a guesthouse with 21 guest rooms and a shared heated pool, half a block from Duval Street.
When is the best time to visit Key West?
Peak season is December through April — dry season, lower humidity, temperatures in the mid-70s, and the best weather for outdoor activities. Summer (June–September) has lower rates and excellent diving visibility but is hot and humid with daily afternoon thunderstorms. Hurricane season runs June through November; the Keys are evacuated for major storms, and travel insurance is strongly recommended for summer bookings.
How far is Key West from Miami?
Key West is approximately 160 miles south of Miami via US-1 — a 3.5 to 4-hour drive that crosses 42 bridges over open water, including the Seven Mile Bridge between Marathon and the Lower Keys. The drive itself is a significant part of the experience; US-1 through the Keys has no parallel route and no exits. Key West International Airport (EYW) has direct flights from a handful of cities; most visitors fly into Miami (MIA) or Fort Lauderdale (FLL) and drive.
What is Old Town Key West?
Old Town Key West — roughly the western third of the island — contains the largest collection of 19th-century frame vernacular architecture in the United States. The buildings are called conch houses, built by ship carpenters using boat-building techniques: lightweight timber frames, wide porches to catch trade winds, louvered shutters, and elevated foundations. The neighborhood is walkable, dense, and shaded by mature tropical trees. It contains the Curry Mansion (1869), the Hemingway House (1851, 907 Whitehead Street), Duval Street, Mallory Square, and the majority of Key West's historic guesthouses and hotels.
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This guide was assembled from the local knowledge of hosts with properties throughout Key West, FL, as indexed by CielStay. The descriptions of restaurants, trails, swimming holes, and local tips reflect what hosts share with guests in their listings — not the observations of a travel journalist or guest reviewer. Photos are sourced from host listing images and are credited to their respective listings. Information about permits and trail conditions may change; always verify with official sources before your trip.