Key West Neighborhoods

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Key West is a small island, made up of distinct neighborhoods, each providing different charm and activities. Check out the different Key West neighborhoods and decide which property is right for your next vacation! 

Truman Annex

Truman Annex is both a neighborhood and military installation. A portion of the Truman Annex has been developed into a gated residential community of luxury homes, townhouses and condominiums designed to capture the historic essence. Situated in a lush garden setting, this location gets its name from the winter White House home of President Harry Truman, now a museum.

Old Town – North of Truman Ave

Old Town is the western part of the island and divided into North and South of Truman avenue. 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, that will captivate you while roaming through one of the prettiest towns in the United States.

Old Town - South of Truman Ave

This district, known as "Uptown Key West", features beautiful Victorian homes, historic cottages and quiet tree lined streets. The neighborhood is only a short walk to an exceptional variety of restaurants, boutiques, and galleries. Close to South Beach, and the Southernmost Point, this is a great location to experience all Key West has to offer.

The Meadows

The Meadows is a residential neighborhood boasting beautiful old homes with varied architectural features. Brightly painted shutters and lush tropical landscapes, make this neighborhood a charming place to live. Neighbors still “talk” over the fence and share bits of local news and opinions. Take a gracious step back in time in this tranquil neighbor.

Casa Marina

The Casa Marina district is built around the Casa Marina Resort; a hotel originally envisioned by Henry Flagler, builder of the Flagler Railroad, built in the 1920’s. This neighborhood boasts large spacious homes of varying styles.  Situated just blocks from the Atlantic Ocean and old town, this is one of Key West’s most desirable neighborhoods.

Midtown West

Midtown west is a quiet neighborhood adjacent to the Casa Marina district. The homes are varying style, from grand spacious homes, historic conch homes, and cottages. It’s just a short walk to Higgs and Smathers beach, as well as White Street pier. Restaurants and galleries are just a stroll away as well as Duval street entertainment.

Midtown East

The homes in the Midtown east vary greatly in size and style. Most of the original homes were built in the 1950’s and 60’s as the islands population expanded from old town. These homes were primarily ground level single family homes and many made of concrete block construction.  Close to all shopping and amenities.

New Town

New Town is on the eastern side of the island and features large homes, big back yards, wide streets and numerous canal properties. With the rambling ranches and bungalows, you’ll find plenty of room in this area of town. It’s convenient for all your needs, with three shopping centers, grocery stores, and various other merchants.

Key West Golf Club

The Key West Golf Club development offers beautiful single family homes and townhouses all in a lush tropical setting.  Surrounded by the Rees Davis 18-hole golf course, it includes amenities such as; two swimming pools, clubhouse, exercise room, gated entrance, and 24 hour security. All this and only 4 miles from Duval St!

Sunset Key

Sunset Key is a 27-acre resort island, located about 500 yards off of Key West directly across from Mallory Square. This no-car island is accessible only by ferry, and offers single-family homes and vacation rentals, surrounded by tropical landscaping. Enjoy quiet island living, just steps away from sandy beaches, tennis courts, spa and the island restaurant.