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.

65 properties available

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

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)

Villa Olivietta

Private Home

$299^.00 - $1,076^.00 / per night

SPIRIT OF KEY WEST was originally built in 1893 and features that authentic Key West charm found in other historic properties such as Hemingway’s House, Asa Tift’s manor and Truman’s Little White House. The vaulted ceilings and Dade County Pine walls harken back to a time when the cigar industry was booming and Key West featured more millionaires p

New Property

Fabulously Fresh New Property!!

Monthly Rental

Spirit of Key West

Private Home

$482^.00 - $1,392^.00 / per night

4 bedrooms

4 baths

8 guests

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

Casa Serendipity

Private Home

$444^.00 - $3,050^.00 / per night

In the same way that the island of Key West has captured the hearts of so many, this charming monthly vacation home will capture yours. ISLAND INSPIRATION combines the appearance and charm of a historic Keys home, with all of the modern conveniences you have come to appreciate. This special home is situated on Margaret Street at the edge of where O

Monthly Rental

Island Inspiration

Private Home

$275^.00 - $1,036^.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 - $11,339^.00 / per night

THE GILDED PINEAPPLE is a classic Key West home located on one of the most desirable streets in Old Town. This completely renovated, historic home gets its’ name from the elegant, oversized golden door knocker shaped like a pineapple that graces the front door – one of the many subtle touches that adds to the charm. THE GILDED PINEAPPLE features a

Monthly Rental

The Gilded Pineapple

Private Home

$387^.00 - $1,050^.00 / per night

3 bedrooms

3 baths

6 guests

SUZY'S PARROT PERCH is a charming apartment that is located in the heart of Old Town on the corner of two historic streets (Whitehead and Virginia) just steps from Duval and two blocks from the Southernmost Point. You couldn't be any closer to the nightlife and attractions on Duval Street (Flamingo Crossing, the famous homemade Key West ice cream p

Suzy's Parrot Perch

Condo

$250^.00 - $1,282^.00 / per night

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

Villa Angelita

Condo

$333^.00 - $2,142^.00 / per night

Traveling with a large group requires a special home. To maximize comfort, large common areas are offered both indoor and outdoor. Private bedroom accommodations with en-suite bathrooms and TVs are a must. And don't forget about the location! This home is easily accessible to the favorites of Old Town for when the group (finally) reaches a decision

Monthly Rental

La Grande Reunion

Private Home

$395^.00 - $1,538^.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

Endless Summer

Private Home

$675^.00 - $4,801^.00 / per night

Don't miss an exceptional opportunity to spend your Key West stay on the grounds of an incredible estate property in the most ideal Old Town location you could imagine. DARLING OF DUVAL is a two-story guest cottage that offers many of the essentials and comforts of a luxury hotel plus the added benefits of an in-home washer & dryer, a private p

HOT 33

Darling of Duval

Cottage

$425^.00 - $2,400^.00 / per night

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

Private Home

$275^.00 - $1,000^.00 / per night

3 bedrooms

3 baths

6 guests

Tell us what you're looking for and someone will contact you with available options.

First Name

Last Name

Phone Number

Email Address

Arrival Date

Departure Date

Comments

I agree Sign me up! I agree to receive information about promotional offers and rental info via phone, email or SMS. You can unsubscribe at anytime. Privacy Policy