Key West Vacation Rentals

Are you looking for Key West rentals that are both luxurious and convenient? Look no further than Last Key Realty! Our properties are strategically located across Key West's most coveted areas, including the historic charm of Old Town, the serene beaches at 1800 Atlantic, the exclusive Truman Annex, and the picturesque Sunset Marina. Plus, we offer rentals near Duval Street, the lively heart of Key West.

Our rentals here in Key West cater to your needs, whether you're planning a quick getaway or an extended stay. Available for nightly, weekly, or monthly stays, our properties offer a range of premium amenities. From fully equipped kitchens for culinary enthusiasts to private pools and outdoor dining spaces for those who love to entertain, we have everything you need to make your stay comfortable.

And for those who can't bear to leave their furry friends behind, our pet-friendly options ensure that no family member misses out on the fun in Key West!

Would you prefer a condo setting? Our vacation condos feature luxurious amenities, including communal pools, spas, and tennis courts.

When planning your stay in Key West, remember that regulations require a transient rental license for short-term stays. As these permits are limited, short-term rental rates may be higher than monthly rentals.

To find the perfect fit for your stay, simply use our user-friendly search bar. Input your travel dates, and our system will show you the most suitable options, including flexible rate options, to ensure you find your ideal Key West rental. At Last Key Realty, we're dedicated to making your stay in Key West genuinely memorable. Don't hesitate to contact our property managers for any help or if you have questions about your booking.

Properties Available 154 properties available
AZURE DAYDREAM, a beautifully renovated waterfront home located 25 miles north of Key West, epitomizes Florida Keys living at its finest. From spending your days on the boat exploring the Lower Keys, to hosting the ultimate family game night in the game room, there’s no shortage of fun to be had at AZURE DAYDREAM. This 4-bedroom home was recently u
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Azure Daydream
Private Home Pet Friendly
$200.00 - $827.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (2)
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
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Sweet Americana
Compound Pet Friendly
$1,300.00 - $6,080.00 / per night
Bedrooms 8 bedrooms
Bathrooms 8 baths
Half-Bathroom 2 half-baths
Guests 20 guests
Rating 5 (18)
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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Villa Olivietta
Private Home Pet Friendly
$299.00 - $1,000.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (5)
OCTOPUS'S GARDEN has been whimsically decorated with furnishings that reflect the laid-back, quirky island life style of Key West. Located in the gated community of Coral Hammock, you will be just down the street from the famous Hogfish Bar & Grill, Roostica Pizzeria, Hurricane Hole Marina & Restaurant and Chico's Cantina. The Key West Golf
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Octopus's Garden
Private Home
$250.00 - $1,144.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (386)
Key West has a unique way of appealing to anyone and everyone that visits the island, and it's easy to see why: the laid-back way of life, the historic charm and walkability of Old Town, and the overall 'good vibes' that the island has to offer those needing an escape from the day to day hustle and bustle of the real world. These same appealing cha
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Good Vibrations
Private Home Pet Friendly
$599.00 - $2,967.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating 5 (175)
When the ‘Welcome to Key West’ sign hits your eye, like a big pizza pie, THAT’S AMORE! If you’ve ever visited Key West, you know how easy it is to fall in love with the charm of this little island. It’s even easier to fall in love when staying in a lavishly decorated and furnished, fully stocked, historic home in the heart of Old Town, and THAT’S A
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That's Amore!
Private Home
$333.00 - $1,125.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 6 guests
SUNDRENCHED REFLECTIONS is very close to Old Town, with access to all the attractions that Key West has to offer. Yet, you'll be in your own world with a large sundrenched balcony overlooking Florida Bay and the Gulf of Mexico beyond. THE PRIVATE GATED COMMUNITY... Sunset Marina is a gated community located on Stock Island, right off the entrance t
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Sundrenched Reflections
Condo
$175.00 - $487.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (10)
According to the classic song, the best remedy for a belly ache is to "put de lime in de coconut and drink 'em bot' up." Last Key Realty now has the best remedy for finding comfortable accommodations for a large group vacationing in Key West: Reserve THE LIME & THE COCONUT and let us handle de rest! THE LIME & THE COCONUT is a compound of t
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The Lime & The Coconut
Compound Pet Friendly
$1,000.00 - $5,080.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half-Bathroom 2 half-baths
Guests 16 guests
Rating 5 (81)
SUNFLOWER MELODIES captures the feeling of a childhood summer, like your bare feet on freshly cut grass, the summer sun gently kissing your skin or the sweet, subtle scent of a field of wildflowers in bloom. A month in Key West is defined by a simpler way of life, with low stress, high fun, and heaps of relaxation - which SUNFLOWER MELODIES provide
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Sunflower Melodies
Private Home Pet Friendly
$222.00 - $765.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
This renovated Old Town estate is designed for the real downtown experience in the Conch Republic, but in a large home-base all your own. SWEET HOME ANGELITA is located right in Old Town, half a block away from Duval Street and smack dab in the center of the entertainment district. You couldn't be any closer to the late-night scene and attractions
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Sweet Home Angelita
Private Home Pet Friendly
$560.00 - $3,398.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 5 (106)
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
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A Royal Affair
Compound Pet Friendly
$1,800.00 - $9,241.00 / per night
Bedrooms 11 bedrooms
Bathrooms 12 baths
Guests 34 guests
ISLAND BLISS is a classic Old Town Key West home, complete with delicate gingerbread accents, a classic Southern front porch with rocking chairs, and lush, tropical foliage tastefully surrounding the property. This beautiful, historic two-story home has been lovingly cared for and restored with a mix of modern touches and traditional Key West influ
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Island Bliss
Private Home Pet Friendly
$250.00 - $720.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests

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