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 102 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
Hot HOT 27
Queen of Louisa
Private Home Pet Friendly
$688.00 - $3,612.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 5 (84)
It doesn't get any 'sweeter' than vacationing with a large group of your closest friends and family in America's Paradise. As a combination of two side-by-side private homes, SWEET AMERICANA not only offers plenty of comfortable accommodations for the whole crew but is an extremely rare find in the center of Old Town Key West. Located at the end of
Sweet Americana
Compound Pet Friendly
$1,430.00 - $6,649.00 / per night
Bedrooms 8 bedrooms
Bathrooms 8 baths
Half-Bathroom 2 half-baths
Guests 20 guests
Rating 5 (18)
Tranquility. Peace. Relaxation. You’ll find these traits are in abundance at GARDEN OF EMMA. The open and airy interior of this exquisite Key West home will keep your group connected and present, while being the perfect complement to the tranquil, tropical exterior. The spacious backyard is your very own private oasis, complete with a lagoon-style
Garden of Emma
Private Home
$800.00 - $3,059.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (4)
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 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)
Modern in the Meadows
Private Home Pet Friendly
$275.00 - $1,015.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating 5 (5)
Finally, a large vacation home where every member of the family will be happy. From the vaulted living room with three couches and a giant 60-inch TV, to the kitchen large enough for a whole team of chefs to prepare dinner, CASA OLIVIANA has it all.THE LIVING AREA...The aforementioned living room is truly big enough for the whole family. The only d
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)
Casa Oliviana
Private Home Pet Friendly
$395.00 - $1,368.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (33)
Perched above the sights and sounds of Duval Street, sits TOP OF OLD TOWN, a recently renovated 2-bedroom private home, located within a secluded community in the heart of Old Town. This hidden gem offers a spacious interior, multiple outdoor spaces, and access to the community pool. Combined with Last Key Realty’s Five Star Guest Services & Co
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New Property New Property
New Property
Top of Old Town
Condo
$366.00 - $1,782.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
BAHAMIAN BAMBOO has been painstakingly decorated and furnished in a sophisticated yet distinctive Bahamian style. Your lifestyle in this home will be very Bahamian as well, with large French doors that open up to provide seamless tropical indoor/outdoor living. The pool is just steps away from the living room sectional or the outdoor dining area. Y
Bahamian Bamboo
Private Home Pet Friendly
$820.00 - $3,132.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (150)
Traveling to Key West with a group deserves the ultimate vacation rental home: plenty of space to stretch out and enjoy time together, separate rooms and bathrooms to enjoy privacy, a private saltwater pool and outdoor lounge area, and off street parking for scooters, and of course, bicycles. THE CONTENTED CRANE checks all of these boxes, and more.
Hot HOT 28
The Contented Crane
Townhome Pet Friendly
$443.00 - $3,118.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (205)
Located in Truman Annex, a gated community with some of the most impressive homes in Key West, this exceptional home stands out from all the rest. NOONA'S MANSION is nestled in a quiet cul-de-sac facing the ocean on a beautifully landscaped piece of property. This impressive home features six spacious bedrooms, a fully equipped kitchen, a stunning
Hot HOT 46
Noona's Mansion
Private Home
$1,600.00 - $6,064.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (273)
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
Oasis on Olivia
Compound Pet Friendly
Bedrooms 9 bedrooms
Bathrooms 9 baths
Half-Bathroom 1 half-baths
Guests 20 guests
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 33
Star of the Seaport
Private Home Pet Friendly
$1,200.00 - $5,356.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (181)
A highlight of any Key West vacation is exploring the island and discovering for yourself Old Town's most treasured restaurants and attractions. The newest discovery awaiting you is a precious ‘gem’ of a home tucked away in a quiet enclave within Truman Annex, Key West’s most exclusive gated community. SALTWATER SAPPHIRE is a newly renovated two-st
Saltwater Sapphire
Private Home
$475.00 - $1,616.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 2 half-baths
Guests 6 guests
Rating 5 (62)

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