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.

73 properties available

SOUTHERN STAR is a modern Key West home nestled in the quiet Meadows neighborhood of Old Town that combines the island way and the sweet life of the South. With wide porches, a breezy interior, cathedral ceilings, and an apparent southern charm, it's easy to see where this home gets its name. In addition to its distinct southern features, this home

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)

Experience the blend of historic charm and modern conveniences at TASTE OF HAVANA. This 2-bedroom, 2-bathroom cottage located ON world-famous Duval Street offers a front-row seat to the vibrant energy of Key West while providing a private pool and off-street parking for those who appreciate the finer things that come with island living. From the pr

Key West is known for all things lime: Key Lime Pies, Margaritas, and now, THE ZESTY LIME, a rare gem in the heart of Old Town Key West that captures the essence of classic Key West in a completely renovated modern design. THE ZESTY LIME includes all of the coveted amenities of a vacation home: a spacious living area, an ideal bedroom and bathroom

Step into VOGUE VILLA, a stylish island escape where timeless Key West charm meets a confident dose of modern luxury. Behind its classic Old Town exterior and welcoming porch, the home has been fully reimagined into a chic retreat layered with curated comforts, designer touches, and a fabulously eclectic aesthetic that feels both relaxed and runway

New Property

Monthly Rental

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

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

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

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

SWEPT AWAY is a meticulously renovated and decorated one-story private home with a refreshing mix of that classic conch home feel we all adore and a new coastal style. This conch cottage has an open living plan and a lovely backyard garden area with a private pool, ideal for relaxing in your oasis just blocks from the famous sites of Old Town Key W

Monthly Rental

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

Maya's Secret Treasure

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

Monthly Rental

Flight of the Flamingo

CASA VICTORIA, located in the heart of Old Town just two blocks from Duval Street, is a large 5 bedroom home built with the charm and quirkiness of early 20th century Key West. Dating back to the Cigar Manufacturers' era, CASA VICTORIA exudes the classic Old Town style that makes Key West such a unique vacation experience. This authentic Conch Hous

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