Nestled in the tropical paradise of the Florida Keys, Key West is a vibrant and enchanting destination that offers a rich history, breathtaking natural beauty, a unique blend of cultures, and numerous activities that will keep you occupied. There is no end to the fun things to do and stunning weather in Key West, and it’s easy to see why it is a loved vacation spot for so many!
Explore the best Key West neighborhoods and find the perfect location to book your rental house in Key West!
New Town
New Town, the dominant and expansive area of Key West, stretches from First Street to Kennedy Drive, extending along Riviera Drive to Patterson Avenue.
This mostly residential region is complemented by the lively “Anywhere USA” enclave along North Roosevelt Blvd, where you’ll find a bustling atmosphere with shopping centers, delectable eateries, and so much more!
Moving eastward, beyond Kennedy Drive, New Town unveils another residential marvel, showcasing picturesque streets adorned with charming homes that embrace an authentic Key West vibe.
Truman Annex
Named after the esteemed President Harry Truman, who cherished this area and spent his winters in his beloved home, affectionately known as ‘The Little White House,’ the Truman Annex is a neighborhood with a captivating history.
At the heart of Front Street stands the magnificent residence that once belonged to President Truman. Today, it has been transformed into the Harry S. Truman Little White House Museum, allowing visitors to step back in time and explore the remarkable legacy of this iconic figure.
Surrounding the museum are meticulously redesigned grounds that were once expansive military territory spanning over 100 acres. This picturesque setting invites leisurely strolls and bike rides, offering a serene escape from the bustling city.
As you venture towards the southern end of the Annex, you’ll encounter charming row townhomes adorned with tin roofs and inviting porches. These architectural gems showcase the timeless beauty of the classic Southern Cottage style, adding a touch of elegance to the neighborhood’s fabric.
Just beyond the Annex gate lies Forty Zachary Taylor, a breathtaking oceanic paradise that has been transformed into a State Park. This pristine area boasts one of the most beautiful beaches on the entire island, too!
Old Town
The world-famous historic waterfront of Old Town Key West takes you back in time to the late 1800s when the visionary founding fathers and mothers of Key West built the first shipping docks, warehouses, restaurants, and magnificent homes that still grace the landscape today.
This area encompasses not only the picturesque waterfront but also the Duval Street area.
Imagine the days when literary legend Ernest Hemingway frequented local waterholes, leaving an indelible mark on the area’s history. Fast forward to the present, and you’ll discover a vibrant atmosphere that pulses with festivals, parades, and a spirit that ignites a sense of adventure within all who visit.
As the sun dips below the horizon, the eclectic nightlife of Old Town Key West springs to life. Prepare to be delighted by a multitude of entertainment options tailored to suit every taste. Indulge in the tantalizing flavors of top-notch Key West restaurants, and satisfy your desire for retail therapy with the many unique shopping opportunities.
Come and experience the allure of Old Town Key West, where history comes alive, festivities abound, and the possibilities for adventure are limitless.
Bahama Village
Nestled between Whitehead, Louisa, Fort, and Angela Streets, Bahama Village is often hailed as the last bastion of “the real Key West.” In the late 1800s, Bahamians traveled from the Bahamas to settle in Key West, bringing their traditions and customs to this delightful island corner.
Walking through the Village’s quaint streets, you’ll be transported to the colorful landscapes of the Bahamas. Clapboard “shotgun” houses painted in hues of white, Caribbean blue, and canary yellow line the streets, exuding a sense of warmth and island charm.
As you explore the Village, the rhythmic beats of music will serenade your ears. Conveniently bordering the downtown shopping area of Old Town Key West, Bahama Village offers the perfect location for your Key West adventure.
Plan Your Visit
If you’re looking for the best Key West vacation rentals for your next vacation, look no further than Historic Hideaways! Whether you’re envisioning a cozy cottage tucked away in Old Town Key West or a luxurious waterfront home with stunning sunset views, we have the perfect place for you! View all of our Key West vacation rentals and book your stay today!
The Meadows
The Meadows is a lovely area situated just west of Bayview Park, with Eisenhower Drive, White Street, Truman Avenue, and Angela Street bordering its enchanting boundaries.
The majority of homes in this neighborhood are the quintessential Key West Conch homes, displaying the classic architecture that has become synonymous with the island. Many of these homes have stood since the late 1800s, adding a sense of history and authenticity to the neighborhood’s tapestry.
Despite its tranquil ambiance, the Meadows still offers the convenience of being within Old Town. You’ll find yourself within walking and biking distance to the vibrant attractions of Duval Street, the captivating allure of the Historic Seaport District, and the delightful array of shops and restaurants that grace White Street.
Casa Marina
Casa Marina, aptly named after the historic hotel Henry Flagler envisioned as the jewel in the crown of his railroad, holds a captivating allure, boasting a legacy of outstanding architecture that spans from the turn-of-the-century to mid-century and modern designs.
Bordered by the majestic Atlantic Ocean to the south and United Street to the north, this neighborhood is perfectly situated to offer an array of recreational activities within walking distance. You can immerse yourself in the wonders of nature at the Wildlife Sanctuary and Indigenous Park and soak up the breathtaking views from the White Street Pier while indulging in the delectable offerings of beachfront restaurants.
Mid Town
Welcome to the heart of Mid-Town Key West—a resolutely residential enclave that emerged from the creation of a landfill in the 1940s and 1950s, enabling the development of early suburban living. The architecture of this neighborhood predominantly showcases the modest yet charming style of mid-century homes, complete with spacious yards that invite relaxation and outdoor enjoyment.
This hidden gem of a neighborhood, a little “off-the-beaten-path,” holds a remarkable advantage with its proximity to the beach, White Street, and New Town Key West. It’s also just a 20-minute bike ride away from the vibrant energy of Upper Duval Street, ensuring you’re always within the island’s bustling attractions.
Book Your Key West Vacation Rental With Historic Hideaways
Discover the magic of Key West by booking the perfect Key West rental with Historic Hideaways!
At Historic Hideaways, we specialize in offering exceptional rentals in Key West, providing you with an unforgettable vacation experience. With our extensive expertise as a trusted local vacation rental provider for over 25 years, we guarantee to bring you the best Key West offers.
Immerse yourself in the tropical paradise that surrounds our luxurious Key West rentals. Bask in the glorious sunshine, explore the breathtaking landscapes, enjoy the stunning Key West weather, and savor tranquil evenings in our delightful accommodations.
Choose from our exquisite rentals in Key West, each designed to provide the utmost comfort and convenience during your stay.
Secure your rental in Key West with us today and make your vacation dreams a reality!