While you browse our Key West rentals for your next island vacation, consider a stay in historic Old Town. Bound at one end by the Gulf of Mexico and the other by the Atlantic Ocean, this area called Old Town is designated as an official U.S. historic district and forms the heart of Key West. It is the center of the island’s early settlement origins and is the home to some of our most popular tourist attractions. Aboriginal Americans, English & Spanish seafarers, and fearsome pirates visited this area frequently during their travels, but it was in the late 1800s when permanent settlers established the first shipping docks, restaurants, skinny dirt roads, churches, and living quarters.
Many streets in this area are named after its founders: John Simonton, John Whitehead, Pardon Greene, and William Pope Duval. Interwoven among the streets is a treasure trove of educational and celebratory establishments to explore. Experience Mallory Square, the Seaport and Harbor Walk, Duval Street, pristine beaches, museums, the aquarium, and your selection of over 200 restaurants, bars, boutiques, souvenir shops, art galleries, and theaters during your stay. Old Town Key West is a neighborhood with a plethora of historical attractions that provide a clear view of the culture that made us who we are today. Browse our Key West Old Town Rentals collection below to find the perfect accommodation for your next getaway!