Old Town Key West Rentals

Experience the charm and history of Key West with Last Key Realty's vacation rentals in historic Old Town. Our handpicked properties offer the perfect blend of luxury and comfort for your stay in one of the island's most iconic neighborhoods.

From cozy cottages to spacious homes with private pools, our Old Town Key West rentals accommodate couples, families, and groups. Each property is thoughtfully decorated and furnished, providing all the amenities you need to feel at home during your stay.

Stroll the streets of historic Old Town and discover the island's unique architecture, vibrant culture, and rich history. Our rentals are just steps away from world-class dining, shopping, entertainment, and some of Key West's most famous attractions, including the Ernest Hemingway Home and Museum, the Key West Lighthouse, and the Southernmost Point.

At Last Key Realty, we're committed to providing exceptional customer service to make your Old Town Key West rental experience unforgettable. Our team is available 24/7 to assist you with any needs or questions that may arise during your stay.

Book your Old Town Key West rental today and plan your dream vacation in paradise. Contact us for more information or browse our properties online. We can't wait to welcome you to historic Old Town Key West!

We also have vacation rentals on Duval Street, near Duval Street, within Truman Annex, and rentals in Sunset Marina.

72 properties available

The moment you arrive at PALMS ON DUVAL, located a few steps from World Famous Duval Street in the heart of Key West, you will feel the laid-back island vibes take over as your vacation officially begins. Tucked away in an unbeatable Old Town location on a dead-end street, this charming three-bedroom, three-bathroom, one-story home offers the perfe

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New Property

After landing in Key West and arriving at your door, FLIGHT OF THE FLAMINGO will have you feeling like it was love at first flight! The light colors, natural wood finishes, and Caribbean-inspired art radiate an energy and warmth reflecting Key West’s tropical vibes. From the rocking chairs on the veranda to the inviting interior and the lushly land

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Monthly Rental

A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)

Flight of the Flamingo

Among the many hidden treasures of Old Town Key West, lives a charming loft-style condo that will melt your heart from the moment you enter. SOUTHARD PEARL is a 2 bedroom second floor condo located in Southard Square, an intimate community located in the heart of the island - a few blocks from Mallory Square, Duval Street and all the attractions Ke

Monthly Rental

With a sense of gracious royalty, QUEEN OF LOUISA will treat you to an unforgettable stay in Key West. Her ideal location, modern interior, private pool and thoughtful touches throughout will ensure you and your group have everything you could want in a vacation rental. QUEEN OF LOUISA offers cozy bedrooms, a fully stocked kitchen and a fantastic o

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While Old Town Key West has its fair share of impressive homes, few can compare to ENVY OF THE ISLAND, a freshly built two-story private home that combines the appearance and charm of a historic Keys home with all of the modern conveniences you have come to appreciate in new construction. This head-turning property boasts five bedrooms - unheard of

Monthly Rental

For a month in Key West it is ideal to harness the comforts of new construction similar to the luxuries of your own home, but keeping the true spirit of Old Town Key West and the magical surprises around every corner. This brand newly constructed home, located a stone's throw from the Southernmost Point, also backs up to the famous Butterfly Museum

Monthly Rental

Dance of the Butterflies

Walking along Duval Street dreaming of the ideal Key West vacation destination, scanning the rooftops for possibilities, at first you’ll miss this hidden gem completely…but once you discover MAYA’S SECRET TREASURE, you will know you have found the ultimate home base to enjoy Key West. Perched above Duval Street, this beautifully modern condo offers

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Maya's Secret Treasure

Travelers from around the world would agree spending a month in Key West is truly a magical experience, especially when you find two classic conch homes made into one. This cozy compound perfectly captures the magic of the island, with its beautiful Dade County Pine walls, tropical decor, and the plunge pool waiting just outside. MARGARET’S MAGIC

Monthly Rental

Margaret's Magic Compound

According to the classic song, the best remedy for a belly ache is to "put de lime in de coconut and drink 'em bot' up." Last Key Realty now has the best remedy for finding comfortable accommodations for a large group vacationing in Key West: Reserve THE LIME & THE COCONUT and let us handle de rest! THE LIME & THE COCONUT is a compound of t

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The Lime & The Coconut

This precious 2 bedroom cottage with its coral front door will charm you from the moment you walk in the front gate. The front porch is private, for some quiet time reading a book. Inside, you'll see that PUERTA CORALINA reflects the simpler side of tropical living but with some useful updates.THE LIVING AREA...The living room of PUERTA CORALINA is

MODERN IN THE MEADOWS proves you can blend modern and tropical styles into a beautifully laidback yet chic home. This fabulous monthly rental shines with its high-end upgrades, refined decor and upscale accommodations. Located in the quiet, sought-after Meadows neighborhood you’ll be treated to a month of relaxation in a newly renovated home that f

Monthly Rental

Modern in the Meadows

If your idea of a vacation includes pampering yourself and indulging in the finer things in life, then a stay at the DUCHESS OF CATHERINE will be your cup of tea. This newly built, professionally designed home is fit for a King and offers plenty of space for all the members of your court. Located on Catherine Street, just steps from Duval Street, y

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