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

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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OASIS ON OLIVIA is the perfect setting for a large group looking to experience a month in Key West in style. As a combination of two side-by-side private homes located in the heart of Old Town, OASIS ON OLIVIA offers a prime location and plenty of comfortable accommodations for everyone, as well as numerous luxuries, including two private heated po

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

SOUTHERNMOST BLISS is a historic Key West eyebrow home that recently underwent a complete renovation, and the result is nothing short of pure bliss. This home was designed to combine the best of classic Key West with luxurious modern comfort. SOUTHERNMOST BLISS features 3 bedrooms in the main house and a 4th bedroom in the Guest House, each with it

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)

SOUTHERNMOST HOSPITALITY V is a luxurious private estate that occupies an entire corner of Old Town's famous Duval Street, just a block from the Southernmost Point. Don't let the address fool you... this upscale home has plenty of privacy in the spacious back yard with a tall fence surrounding the large private pool. Privacy also comes in the form

Southernmost Hospitality V

On an island where being unique is embraced and the unusual is quite ordinary, lives a home that embodies that colorful spirit. ANGELA’S ECLECTIC GALLERY is a lovingly restored historic home that has been designed and outfitted to include all the modern conveniences paired with exotic and playful touches throughout. Original local artwork and hand-

Monthly Rental

Angela's Eclectic Gallery

Nestled in the heart of Old Town Key West, BLUE HERON’S HIDEOUT is a newly renovated ranch-style home that perfectly blends historic charm with modern luxury. Featuring 4 bedrooms each with an en-suite bathroom, a heated pool, home office, and off-street parking, this exquisite home is a private oasis for discerning travelers seeking both convenien

Monthly Rental

This modern Old Town condo is designed for the real downtown experience in the Conch Republic, ideal for anyone looking to indulge in Key West’s famous late night scene. VILLA ANGELITA is located right in Old Town, half a block away from Duval Street and smack dab in the center of the entertainment district. Although this property does not include

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

SOUTHERNMOST HOSPITALITY VII is a luxurious private estate that occupies an entire corner of Old Town's famous Duval Street, just a block from the Southernmost Point. Don't let the address fool you... this upscale home has plenty of privacy in the spacious back yard with a tall fence surrounding the large private pool. Privacy also comes in the for

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Southernmost Hospitality VII

This ultimate Key West dream home is nestled in the highly desirable residential Old Town neighborhood of Solares Hill, just a quick walk from Duval Street and the Historic Seaport areas. No expense has been spared in upgrading and furnishing VILLA OLIVIETTA; the most up-to-date appliances and technology can be found in each room. The comfortable a

Monthly Rental

HAVANA ESPECIAL is a charming, single-level 2-bedroom cottage located directly on the world-famous Duval Street in Old Town Key West. This inviting retreat features two private suites and a fully equipped kitchen, ensuring a comfortable stay just steps away from the island's best dining, shopping, and entertainment. Guests can enjoy the quintessent

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