Rentals near Duval Street

Although Key West is a small island, many visitors prefer the luxury of simply walking to all of their favorite spots. Staying near Duval Street allows you to escape Duval Street's action while still being a short walk from the main attractions.

 A location within eight blocks of Duval Street (up to one mile away) can facilitate a perfect balance of peace in your vacation home with the freedom to walk back and forth to the fun of Duval Street at your leisure. 

For those looking for a balance of a prime location with the peace of an escape to your Key West rental home, here is a list of our homes within walking distance of Duval Street. Or, search for rentals on Duval Street. 

If you have any questions, don't hesitate to get in touch with one of our Key West vacation rental specialists today.


Properties Available 104 properties available
Hidden amongst the thick of Old Town Key West, within Truman Annex, Key West's most exclusive gated community, lives a 'gem' of a home that will surely capture your heart's desire from the moment you lay eyes on it. JASMINE JEWEL is a two-story private home that not only transcends island living at its finest but also offers an ideal location for e
Hot HOT 37
Jasmine Jewel
Private Home
$600.00 - $2,401.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (95)
VILLA BAHAMA is located at The Foundry in the Truman Annex, Key West's most exclusive gated community. You'll be just around the block from Mallory Square, Duval Street and all the attractions Key West has to offer, yet you'll benefit from the peace and quiet that the Truman Annex is known for. Smoking is not permitted in any Last Key Realty home.
Villa Bahama
Townhome
$350.00 - $1,125.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (220)
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
Hot HOT 33
Endless Summer
Private Home Pet Friendly
$675.00 - $4,040.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (221)
For a truly over-the-top Key West stay with your entire group, whether that be the whole family or your closest friends, STAR OF THE SEAPORT has the location, amenities, layout, and extra guest service to help host the island trip you envision. STAR OF THE SEAPORT is a luxurious private estate that occupies an expansive space on an iconic street in
Hot HOT 51
Star of the Seaport
Private Home Pet Friendly
$1,200.00 - $5,331.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (183)
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
Hot HOT 34
Duchess of Catherine
Private Home Pet Friendly
$850.00 - $4,080.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 5 (15)
Hunting for the perfect Key West vacation home can feel like a daunting task. However, once you discover TRUMAN’S TROVE, you’ll know that you’ve struck gold! This two-story private home has been beautifully furnished and designed to the highest standard. In addition, TRUMAN’S TROVE offers an ideal location within Truman Annex, Key West’s most exclu
Hot HOT 46
Truman's Trove
Private Home
$475.00 - $1,488.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (4)
When exploring Old Town Key West it is typical to stumble upon a surprise tropical bloom that reminds you of the magic of the island you have found yourself on. At the right time of year when enjoying the private garden of this townhouse, you may look up into the trees and spot a bunch of bananas smiling down on you. BANANA BLOSSOMS surprises you w
Hot HOT 38
Banana Blossoms
Townhome
$430.00 - $1,453.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (84)
Located on Solares Hill in the heart of Old Town, HAVANA HOUSE captures the simple elegance of Key West's Conch homes of the fifties, when it was still possible to sail to Havana.THE LIVING AREA...The living room of HAVANA HOUSE has a vaulted ceiling, with walls of Dade County Pine. There is a large flat screen TV and comfortable seating for everyo
Hot HOT 28
Monthly Rental Monthly Rental
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)
Havana House
Private Home Pet Friendly
$225.00 - $815.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (51)
A stay at the DUKE OF CATHERINE is fit for a Queen to bring her King! From the crisp, clean decor to the large hot tub and the spacious master bedroom, the DUKE OF CATHERINE has everything his Majesty could desire. This freshly built, professionally designed home is the perfect size for a weekend rendezvous or an extended stay with the royal family
Hot HOT 35
Duke of Catherine
Private Home Pet Friendly
$375.00 - $1,780.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (42)
A trip to Key West is like a breath of fresh air! The sounds of rustling palm trees, the scent of fragrant flowers and the smell of salt air are the rejuvenation that only the tropics can provide. This home is a breath of Key West fresh air, or BRISA FRESCA, a timeless, beach-inspired home that seems to be straight out of the pages of Coastal Livin
Brisa Fresca
Private Home
$860.00 - $2,294.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (272)
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 Pet Friendly
$2,185.00 - $9,485.00 / per night
Bedrooms 13 bedrooms
Bathrooms 13 baths
Half-Bathroom 2 half-baths
Guests 32 guests
Rating 5 (9)
For the ultimate stay in America's Paradise, what could be more perfect for your whole group than AMERICANA TROPICALE? This festive and patriotic home will promise a one-of-a-kind island experience. AMERICANA TROPICALE has 4 spacious bedrooms each complete with its own en-suite bathroom for privacy, a private saltwater pool, a fully equipped kitch
Hot HOT 52
Americana Tropicale
Private Home Pet Friendly
$625.00 - $3,193.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating 5 (315)

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