Book Direct & Save

At Last Key Realty, located in Key West, we work directly with homeowners to ensure you receive the best possible rental rate on your vacation rental property! Search our wide inventory of Key West Home Rentals, Condo Rentals, Rentals With Pools, Luxury Rentals, and more!

WHAT ARE THE BENEFITS?

When you book directly through a Vacation Rental Management Company like Last Key Realty, you not only get the best rate possible, but you also receive local assistance before and during your vacation! Cut out the middleman and book directly at the source. There are a lot of vacation rentals located in Key West, FL, and we can guarantee all of the vacation rentals in our program are well-managed and properly maintained. With a variety of amenities to select from, you are sure to find something for every member of your vacation crew.

NO ADDITIONAL FEES

Online Travel Agencies (OTA's) like VRBO, Tripadvisor, Airbnb and Expedia now charge you a service fee to book on their sites. Fees up to 20% are added to the cost of your reservation when you book through a third-party site. Save yourself those fees and book direct!

LOCAL SERVICE & EXPERTISE

To book at the lowest possible rate and get local knowledge and expertise, reserve online today or call us at 305.292.6266. Our staff is here to provide you with the highest level of customer service. We look forward to having you stay with us soon!

156 properties available

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

NATURE'S EDGE is a well maintained condo that is located at 1800 Atlantic Blvd on the beach, just steps from the ocean and sand in your toes. You'll enjoy peace and quiet on your balcony, with the Key West Nature Preserve just outside your door. NATURE'S EDGE is located in an upscale private community within walking or biking distance to all of you

25% Off Your Stay!!

Save 25% off on any stay through June 14, 2026 due to construction at the complex! 25% discount is reflected in quoted rate. (FYI - a unit will never be rented while its balcony is being worked on). Call us with any questions.

Life in the Florida Keys is all about spending time outdoors, indulging in the things you love with the ones you love; and BLUE HORIZON is the perfect vacation home to experience Keys living for yourself. Whether your ideal day is floating around the large pool with a cold drink in hand, cruising the waters of the Lower Keys in your boat, or gather

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)

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

Mariner's Hidden Haven

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

Monthly Rental

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

Monthly Rental

Sundrenched Reflections

Formerly known as Playland in Paradise, the ultimate Keys vacation awaits you at BAYPOINT OASIS! This spacious waterfront property is perfect for large groups, featuring an open floor plan, six bedrooms, including three master suites, and expansive outdoor space. BAYPOINT OASIS offers every amenity you could ask for in a vacation home… and then som

Monthly Rental

For many, the artistic island culture of Key West is an intricate piece of its magic. THE ARTISTS' MUSE is an ode to that notion. This home, with its rich history of artists living in residence or visiting as guests, has been recently redesigned to celebrate art, culture, and the upscale island life. A spacious main living and dining area, a brand

Monthly Rental

This freshly renovated condo is located at 1800 Atlantic Blvd on the beach, just steps from the ocean and sand in your toes. You'll be able to enjoy quiet afternoons at CONCH IN THE TREETOPS with those balmy Key West breezes wafting through the floor-to-ceiling glass doors, while sitting on your private balcony surrounded by the palm tree tops. CON

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Conch in the Treetops

SUITE SANCTUARY is a luxurious penthouse condo that overlooks the ocean and is certain to be your haven from everyday life. This newly renovated condo features many delights throughout, from the vaulted ceilings to the fresh tile floors reminiscent of a walk on the beach. The large balcony offers a place to relax and enjoy the warm Florida weather

25% Off Your Stay!!

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

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

Southernmost Hospitality V

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