Find Your Ideal Key West Vacation Home

Your Island Getaway Awaits

At Last Key Realty, we love Key West. We are your top choice for finding houses to rent in Key West. Need a small place for a romantic trip? Or a big house for your family? We have options that will suit all of your needs while perfectly capturing the spirit and joy of Key West.

Our houses are comfy and have a local style. You'll find our rentals in the best areas of Key West, from the historic streets of Old Town to the homes and condos on 1800 Atlantic.

Want to see all of our vacation rentals on the island? Check out our Key West Vacation Rentals page. Want a pet-friendly place near Duval Street? Or a beachfront house with an ocean view near the Truman Annex? We have the perfect rental for your Key West trip.


Properties Available 93 properties available
SPIRIT OF KEY WEST was originally built in 1893 and features that authentic Key West charm found in other historic properties such as Hemingway’s House, Asa Tift’s manor and Truman’s Little White House. The vaulted ceilings and Dade County Pine walls harken back to a time when the cigar industry was booming and Key West featured more millionaires p
Hot HOT 28
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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)
Spirit of Key West
Private Home
$482.00 - $1,163.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (1)
The moment you arrive at this midtown mansion, you’ll know your time in Key West is going to be special. The circular driveway and covered portico provide a grand entrance, which set the stage for what awaits you inside. At over 3,900 square feet, ISLAND OPULENCE is one of the largest private residences in Key West. This impressive ranch-style home
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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)
Island Opulence
Private Home Pet Friendly
$250.00 - $732.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 11 guests
Rating 5 (3)
You don’t often find new construction in Old Town, the historic district of Key West known for classic conch homes and walkable streets, but recently a spectacular new home was built smack dab in the middle of it all. CASITA OLIVIETTA is a newly built breathtaking home that allows you to enjoy the luxury of brand-new construction in the prime locat
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)
Casita Olivietta
Private Home Pet Friendly
$215.00 - $775.00 / per night
Bedrooms 3 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 8 guests
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
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Americana Tropicale
Private Home Pet Friendly
$625.00 - $3,196.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating 5 (315)
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 38
Truman's Trove
Private Home
$475.00 - $1,531.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (4)
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
A Royal Affair
Compound Pet Friendly
$1,800.00 - $9,309.00 / per night
Bedrooms 11 bedrooms
Bathrooms 12 baths
Guests 34 guests
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
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Southernmost Hospitality VII
Compound Pet Friendly
$900.00 - $5,953.00 / per night
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half-Bathroom 1 half-baths
Guests 16 guests
Rating 5 (206)
This precious 2 bedroom cottage with its coral front door will charm you from the moment you walk in the front gate. The front porch is private, for some quiet time reading a book. Inside, you'll see that PUERTA CORALINA reflects the simpler side of tropical living but with some useful updates.THE LIVING AREA...The living room of PUERTA CORALINA is
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Puerta Coralina
Private Home Pet Friendly
$370.00 - $2,067.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (543)
Escape the “changing tides” of your day-to-day routine by spending a month in the Keys. MARINER’S HIDDEN HAVEN provides an ideal island setting for re-centering your compass by way of your own private waterfront retreat. Picture mornings sipping coffee on the dock, lazy days by the pool, and beautiful sunsets on your boat. The home’s open layout an
Monthly Rental Monthly Rental
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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)
Mariner's Hidden Haven
Private Home Pet Friendly
$175.00 - $551.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (4)
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
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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)
Havana House
Private Home Pet Friendly
$225.00 - $815.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (51)
Travelers from around the world would agree spending a month in Key West is truly a magical experience, especially when you find two classic conch homes made into one. This cozy compound perfectly captures the magic of the island, with its beautiful Dade County Pine walls, tropical decor, and the plunge pool waiting just outside. MARGARET’S MAGIC
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)
Margaret's Magic Compound
Compound Pet Friendly
$333.00 - $1,101.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 8 guests

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