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.

76 properties available

ISLAND BLISS is a classic Old Town Key West home, complete with delicate gingerbread accents, a classic Southern front porch with rocking chairs, and lush, tropical foliage tastefully surrounding the property. This beautiful, historic two-story home has been lovingly cared for and restored with a mix of modern touches and traditional Key West influ

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)

Island Bliss

Private Home

$225^.00 - $760^.00 / per night

3 bedrooms

2 baths

8 guests

THE DUKE & THE DUCHESS is a compound fit for a Queen, her King, and their whole court! These newly built, professionally designed side-by-side homes have everything you could desire for a large group vacation - a prime location, coveted amenities, and plenty of space. Your stay at the THE DUKE & THE DUCHESS also includes Last Key Realty's F

The Duke & The Duchess

Compound

$1,200^.00 - $6,063^.00 / per night

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

Southern Star

Private Home

$265^.00 - $1,015^.00 / per night

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

New Property

Southard Pearl

Condo

$138^.00 - $551^.00 / per night

2 bedrooms

2 baths

5 guests

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

Private Home

$275^.00 - $1,015^.00 / per night

In the Historic Seaport area of Old Town, there is a house that will behold your eye. At first glance you'll see that HEAVENLY ZEN is beautifully maintained with carefully tended landscaping; however, nothing will prepare you for what is inside. As you walk in, you will feel an immediate sense of peace and relaxation. All of the spaces in this meti

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Monthly Rental

Heavenly Zen

Private Home

$345^.00 - $1,243^.00 / per night

Located across the street from Blue Heaven, above the delicious La Creperie French Cafe, sits THE PIRATE’S PENTHOUSE. This hidden gem is ideally located in the heart of Bahama Village and within walking distance to everything Duval has to offer. THE PIRATE’S PENTHOUSE has touches of maritime decor sprinkled throughout this spacious condo, complet

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The Pirate's Penthouse

Condo

$333^.00 - $1,724^.00 / per night

Sometimes in life a 'stroke of good fortune' leads you to discover something so delightful at a moment when you're not even looking for it. When strolling through the streets of Old Town Key West, you may be fortunate enough to stumble upon a home with the perfect combination of quintessential charm and the conveniences of modern amenities. CASA SE

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Casa Serendipity

Private Home

$444^.00 - $2,446^.00 / per night

Coordinating the entire gang for a dream Key West wedding, reunion, or simply a vacation of a lifetime is hard enough... let Last Key Realty make the accommodations easy for you. ALL TOGETHER NOW is an entire block of private homes just steps from Duval Street, all yours to enjoy and with everything needed for a large group getaway: a total of thir

All Together Now

Compound

$2,185^.00 - $9,514^.00 / per night

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

Villa Olivietta

Private Home

$267^.00 - $1,000^.00 / per night

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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Casa Victoria

Private Home

$995^.00 - $5,007^.00 / per night

All year long you dream of a getaway to capture that feeling of Key West's ENDLESS SUMMER - carefree days spent tooling around Old Town on bicycles or wandering the island streets in flip flops with the sun warming your shoulders. No plans, nowhere to be, no deadlines - only a to-do list of making memories with your family and friends and possibly

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Endless Summer

Private Home

$675^.00 - $4,052^.00 / per night

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