Vacation Rentals in Key West on Duval Street

Every major destination has a “main street.” In Key West, our hub of activity, attractions, restaurants, shopping, and nightlife is on Duval Street.

Because it is only a two-mile road stretching from the Southernmost part of the island to the Cruise Ship port, Duval Street can be walked end-to-end in the afternoon. Still, it is nearly impossible to experience all Duval Street offers in a day or even a week. Key West Foodies will find a never-ending array of dining options, from small walk-up bodegas to upscale restaurants touting competitive accolades. From street performers to real estate offices and t-shirt shops to upscale boutiques, Duval Street is a magical mix of culture and life on the island of Key West. 

A vacation rental on Duval Street location can come with heavier foot traffic and the chance for a bit more noise outside. But staying right in the center of the action is sure to create an experience to remember! 

For those ready for the center of the action, here is a list of our Key West vacation house rentals on Duval Street.


Properties Available 5 properties available
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
Hot HOT 34
Top of Old Town
Condo
$333.00 - $1,957.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
SOUTHERNMOST HOSPITALITY V is a luxurious private estate that occupies an entire corner of Old Town's famous Duval Street, just a block from the Southernmost Point. Don't let the address fool you... this upscale home has plenty of privacy in the spacious back yard with a tall fence surrounding the large private pool. Privacy also comes in the form
Hot HOT 33
Southernmost Hospitality V
Private Home Pet Friendly
$800.00 - $5,586.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (7)
There’s no doubt you’ve heard of Duval Street; phenomenal restaurants, eclectic shops and legendary nightlife. This immaculate condo is just a half block away, giving you access to everything Duval Street has to offer while still allowing you to get a restful night’s sleep. SOUL OF DUVAL truly captures the essence of what makes Key West so special,
Soul of Duval
Condo
$240.00 - $1,340.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (41)
Walking along Duval Street dreaming of the ideal Key West vacation destination, scanning the rooftops for possibilities, at first you’ll miss this hidden gem completely…but once you discover MAYA’S SECRET TREASURE, you will know you have found the ultimate home base to enjoy Key West. Perched above Duval Street, this beautifully modern condo offers
Maya's Secret Treasure
Condo Pet Friendly
$599.00 - $3,500.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (79)
SOUTHERNMOST HOSPITALITY VII is a luxurious private estate that occupies an entire corner of Old Town's famous Duval Street, just a block from the Southernmost Point. Don't let the address fool you... this upscale home has plenty of privacy in the spacious back yard with a tall fence surrounding the large private pool. Privacy also comes in the for
Southernmost Hospitality VII
Compound Pet Friendly
$900.00 - $7,139.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Guests 16 guests
Rating 5 (84)

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