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 108 properties available
As soon as you enter, you'll feel like you stepped into a dream. Welcome to DEEP BLUE DREAMS, a modern coastal retreat in the heart of Truman Annex, Key West’s most exclusive neighborhood. This freshly updated 2 bedroom, 2.5 bathroom condo brings a new level of style to island living — sleek and modern, yet relaxed and inviting, with subtle touches
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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)
Deep Blue Dreams
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 4 guests
Rating Rating Rating Rating Rating 5 (1)
Finding high-end accommodations for a large group vacation can be a challenge... let Last Key Realty make it easy for you with this one-of-a-kind compound. A ROYAL AFFAIR is the combination of three homes that offer everything a large group could desire in a Key West vacation home - a total of eleven bedrooms, twelve full bathrooms, three open livi
Hot HOT 30
A Royal Affair
Compound Pet Friendly
Bedrooms 11 bedrooms
Bathrooms 12 baths
Guests 34 guests
Rating Rating Rating Rating Rating 5 (2)
Seals & Crofts said it best: ‘Diamond Girl, you sure do shine.’ Formerly known as Seventh Heaven, DIAMOND GIRL is a stunning two-story private home that epitomizes island living, with its’ distinct exterior eyebrow design, ample indoor and outdoor living space, and comfortable accommodations. Once here you’ll quickly realize this peaceful oasis
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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)
Diamond Girl
Private Home
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (25)
If you’ve recently heard the Siren’s call beckoning you to Key West, it might be because you were drawn by the SIREN’S SERENADE luxurious interior, lush private backyard, and dream-like location. The moment you enter the gate, you’ll meet the Siren posed in her tropical garden. You’ll come around the lavish and very private pool area to enter this
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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)
Siren's Serenade
Private Home
Bedrooms 5 bedrooms
Bathrooms 3 baths
Half-Bathroom 2 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (15)
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
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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 Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (5)
Like many highlights of Key West, THE ADMIRAL'S ESTATE celebrates a rich history of the island while embracing a modern restoration. THE ADMIRAL'S ESTATE is a true historic Key West home, originally built for a high-ranking Naval Officer in the early 1900s. This impressive estate is armed with two living areas, a top-of-the-line gourmet kitchen, cl
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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)
The Admiral's Estate
Private Home
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (3)
Finding a compound like THE THREE MERMAIDS in Key West is as rare as finding actual mermaids! From the pristine, modern decor, to the fun, nostalgic appliances and the ample amount of space in an ideal Old Town location, this compound is truly a one-of-a-kind. Featuring 3 stunning, freshly-built homes on one lot, with a beautiful swimming pool betw
Hot HOT 25
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)
The Three Mermaids
Compound Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 12 guests
CASA AVILA combines a rich history with a desirable Old Town location. Located two blocks from both the waterfront and Duval Street, this beautiful home is considered one of Old Town's original Grande Dames and proudly displays a historical preservation star. CASA AVILA was Key West's first prominent art gallery and one of the original homes in Old
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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 Avila
Private Home
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (2)
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
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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)
Bahamian Bamboo
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (158)
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
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Star of the Seaport
Private Home Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating Rating Rating Rating 4.9 (207)
You have many choices when choosing where to stay in Key West, but the most unique way to get an authentic Key West experience is by spending your vacation in a classic conch cottage smack dab in the heart of Old Town. You know what they say - “In a world full of apples, be a pineapple.” Whether you’re on a writer’s retreat or simply need an escap
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)
The Poetic Pineapple
Private Home Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating Rating Rating Rating Rating 5 (8)
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 Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (254)

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