Your Guide to Old Town Key West

Imagine stepping into a tropical paradise filled with vibrant colors, rich history, and the rhythmic charm of island life. Welcome to Old Town Key West—a place where every street corner has a story to tell, and every home whispers of times past. Covering just 5 square miles, Old Town is the heart and soul of Key West, offering visitors a unique blend of architectural beauty, culinary delights, and world-famous attractions.

But to truly immerse yourself in everything this magical island has to offer, it’s crucial to stay right in the heart of Old Town. At Historic Key West Vacation Rentals, we provide the perfect base from which to explore this unforgettable destination. Whether you're looking for a cozy conch house or a luxurious Victorian mansion, we’ve got you covered.

Why Old Town Key West Is the Best Place to Stay

Old Town Key West isn’t just another tourist destination; it’s a living, breathing snapshot of history, art, and culture. Known for its narrow streets lined with pastel-painted homes, lush tropical gardens, and historic landmarks, this area is a walkable treasure trove of attractions. Staying here means you’ll be close to everything that makes Key West special—Duval Street, the Ernest Hemingway Home, Mallory Square, and more.

Did you know? Old Town Key West has the largest collection of wooden-frame buildings in Florida, dating back to the 19th century. Many of these homes have been lovingly restored to preserve their original charm, creating a distinct blend of the old and the new.

Old Town is where you’ll find the island’s best restaurants, most iconic bars, and an array of boutique shops that make for perfect afternoon strolls. From lively Duval Street, stretching from the Atlantic Ocean to the Gulf of Mexico, to the quiet backstreets where roosters still roam, Old Town offers an experience like no other. Whether you're here for the nightlife, the history, or simply to soak in the laid-back island atmosphere, staying in Old Town is the key to experiencing the real Key West.

A Snapshot of Old Town Key West’s Unique Architecture

Key West’s architectural styles are as diverse as its culture, reflecting influences from the Caribbean, New England, and beyond. Each home in Old Town has its own personality, and walking through these neighborhoods feels like stepping back in time.

1. Conch Houses

The conch house is perhaps the most iconic of all Old Town architectural styles. Built by early settlers, these homes feature airy designs that encourage island breezes to flow through. With steep metal roofs, wide verandas, and pastel-colored facades, conch houses are a reflection of both practical and aesthetic design, built to withstand tropical weather while exuding Key West’s unique character.

Staying in a conch house gives you the chance to live like a local, soaking up island breezes from your veranda and enjoying the island's vibrant sunsets.

2. Victorian Mansions

Victorian mansions are a testament to Key West’s prosperous past. Built during the island’s 19th-century economic boom, these stately homes are adorned with intricate woodwork, wrap-around porches, and tropical landscaping. Known for their dramatic flair, Victorian mansions offer a glimpse into the grandeur of the past.

Many of these mansions have been transformed into luxury vacation rentals, giving guests the chance to experience both history and elegance during their stay.

3. Shotgun Houses

Compact and efficient, shotgun houses are named for their long, narrow layout—legend has it that you could fire a shotgun through the front door and it would travel straight out the back. These homes were originally built to maximize space on small lots and have a distinct Caribbean influence. Their open layout allows for cooling breezes to travel through the home, making them a perfect choice for those looking for a cozy, authentic stay.

4. Bahamian-Style Homes

The Bahamian influence is everywhere in Old Town Key West. Early settlers from the Bahamas brought their colorful, lively style of architecture with them. These homes are often painted in bright, joyful colors and feature double-hung windows and louvered shutters. Staying in a Bahamian-style home offers a cheerful and inviting experience, perfect for soaking up the Key West sunshine.

Where to Stay in Old Town Key West: The Best Vacation Rentals

At Historic Key West Vacation Rentals, we offer a selection of beautifully restored properties in the heart of Old Town. Whether you’re visiting for a romantic getaway, a family vacation, or a solo retreat, we have the perfect home to make your stay unforgettable.

1. La Casita en Cima

Situated in the heart of Old Town, La Casita en Cima is a true architectural gem. This home won the 2016 Historic Florida Keys Foundation Preservation Award, and it’s easy to see why. A full renovation has incorporated modern amenities while preserving the original charm of the home. Located less than two blocks from the lively scene of Duval Street, this 2-bedroom, 2-bath property offers a private fenced yard, a heated pool with a waterfall, and a covered lanai for outdoor dining.

Imagine enjoying a cocktail by the pool or dining alfresco after a day of exploring Old Town. La Casita en Cima offers a luxurious, yet authentic, Key West experience.

2. Villa Josine

Villa Josine is one of Old Town Key West’s most distinguished eyebrow houses—a unique style designed to keep the second story cool in the tropical heat. Now fully renovated with air conditioning and high-end amenities, this home offers 4 large bedrooms and ensuite baths, making it perfect for families or larger groups. Outside, you’ll find a private pool and a covered deck surrounded by lush tropical landscaping.

With its mix of modern luxury and historic charm, Villa Josine is ideal for those looking to experience Key West in style. Located just two blocks from Duval Street, you’ll be in the heart of the action while still enjoying the peace and quiet of a secluded neighborhood.

What to Do in Old Town Key West: Must-See Attractions

Staying in Old Town means you’ll be just steps away from some of the island’s most famous attractions. Whether you’re a history buff, an adventure seeker, or simply looking to relax, there’s something for everyone in Old Town Key West.

1. Ernest Hemingway Home and Museum

No trip to Old Town Key West is complete without a visit to the Ernest Hemingway Home and Museum. The iconic author lived here in the 1930s, and the house has been preserved as a museum filled with original furniture, artifacts, and—of course—Hemingway’s famous six-toed cats.

2. Duval Street

Duval Street is the beating heart of Old Town Key West. Stretching from the Gulf of Mexico to the Atlantic Ocean, this lively street is home to some of the island’s best restaurants, bars, and shops. Whether you’re looking to dance the night away or simply people-watch from a café, Duval Street offers endless entertainment.

3. Mallory Square

For a picture-perfect sunset, head to Mallory Square. Every evening, crowds gather here to watch the sun dip below the horizon in a blaze of orange and pink. The square is also home to street performers, food vendors, and local artisans, making it the perfect spot to soak up the Key West vibe.

4. Southernmost Point

Snap a photo at the Southernmost Point buoy, marking the southernmost tip of the continental United States. This iconic landmark is just a short walk from many Old Town vacation rentals and offers a great opportunity to capture a memory of your Key West adventure.

How to Choose the Perfect Rental in Old Town Key West

With so many beautiful properties available, it can be hard to choose where to stay. Here are a few tips to help you find the perfect vacation rental:

1. Proximity to Attractions: If you want to be close to the action, look for rentals near Duval Street or Mallory Square. For a quieter stay, consider properties tucked away on Old Town’s charming side streets.
2. Size and Layout: Traveling solo or with a partner? A cozy conch house might be the perfect fit. Bringing the whole family? Opt for a larger Victorian mansion or eyebrow house with plenty of space for everyone.
3. Amenities: From private pools to outdoor dining areas, many rentals in Old Town come with luxurious amenities. Make sure to choose a property that offers everything you need to make your stay comfortable and relaxing.

Book Your Stay in Old Town Key West Today!

Old Town Key West offers a vacation experience like no other, where history, culture, and tropical beauty come together to create a magical destination. At Historic Key West Vacation Rentals, we’re proud to offer a collection of stunning homes that put you right in the heart of it all.

Ready to start your adventure? Explore our full range of vacation rentals and find your perfect home away from home. Whether you’re here for a weekend or a month, we’ve got the perfect spot for you to soak up the best of Old Town Key West.