Key West's Historic Old Town and Cultural Legacy

Old Town Key West
by Historic Key West Vacation Rentals

Wanderers, adventurers, and vagabonds unite in Key West. This is the place where you'll get a taste of Caribbean flavor without ever leaving the United States. It's the southernmost point in the U.S. that's famous for watersports, a lively nightlife, beaches, historic sites and pastel-colored architecture. There's also an ecletic mix of politics, diversity, lifestyles, and a brilliant mixing of cultures and social classes.

Historic Old Town - Victorian-Style Homes & Duval Street

The famous historic Old Town Key West waterfront on the gulf side of the island and the original lower Duval Street area, encompasses this district. Here the founding fathers and mothers of the late 1800's built the first shipping docks and warehouses, restaurants and grand homes, that stand today as one of the largest and most impressive collection of turn-of-the-century architecture. From larger Greek Revival Victorians to charming shot gun cottages, many of these alluring structures have been restored and renovated to stand in their gleaming glory. Today this district includes famous waterfront restaurants and bars, retail stores, museums, fishing and sailing charters, a large variety of historic homes, and Mallory Square.

Ernest Hemingway

"It's as if an imagination is intermingling salt water with desert, sea with plain, creatures of the deep with creatures of the bush." Hemingway discovered Key West on a trip home from Paris. He fell in love with its charms and said it was like being in another country. It was a place where he could indugle his love of sportfishing, as he sailed around the Keys and fished the Gulf Stream. When not sailing or bringing in record-breaking catches, Hemingway was writing. His tenure in Key West saw the publication of A Farewell to Arms, Death in the Afternoon, and many short stories. Every July, Key West celebrates Hemingway's birthday with a week long festival. It's a weeklong celebration of all things Hemingway with cultural events, fishing tournaments, lookalike contests and more. Hemingway's home is now a museum and the most popular tourist attraction in Key West. The house and its grounds are still inhabited by decendants of the writer's beloved cats; half of which are polydactl, sporting six toes on each paw. 

Tennessee Williams

One of America's most famous playrights, Tennessee Williams called Key West home for more than 30 years. It's rumored he may have finished up A Streetcar Named Desire on one of his stays on Duval Street and soon after, he made Key West his home. Every March, Williams’ birthday is celebrated with play productions, contests, and movie screenings at the Tropic Cinema. The auditorium of the Monroe Public Library is named for him. Later, the Tennessee Williams Fine Arts center opened. An exhibit celebrated his 100th birthday. Its success brought about the Tennessee Williams Museum a decade later. Williams is also credited with attracting attention to Key West’s gay friendly atmosphere. 

Book Your Stay in Historic Old Town 

Be our guests and experience living like a Key West local in historic Old Town. Ashe House-Monthly Rental is north of Truman Avenue in a quiet residential area within walking or biking distance of several shops, galleries, and restaurants. Lilly's Pad-Nightly Rental is just a half block from Duval Street, near the Key West Butterfly Museum and Southernmost Point. You will enjoy this quieter yet walkable side of town near finer shops, galleries, and restaurants. When you choose Queen Conch-Nightly Rental, you'll find a majority of the tourist attractions are located here as well as numerous restaurants, shops and galleries. The neighborhood boasts historic homes, shotgun and conch style homes. 

From fresh catch-of-the-day dining to grand watersport adventures and the most spectacular sunsets in the "Floribbean", Key West's Old Town and cultural legacy will have you living like a local in no time. How soon can you get here?