Key West House Rentals

Discover the charm of Key West with Last Key Realty, your premier choice for Key West house rentals. Whether you're seeking a cozy bungalow for a romantic getaway or a spacious estate for a family vacation, our portfolio of properties captures the unique essence of the "Conch Republic."

At Last Key Realty, we are more than just a vacation rental broker; we are enthusiasts of all Key West offers. Our properties are thoughtfully designed and furnished to ensure you feel the comfort of home with a touch of local flair. From the historic streets of Old Town to the serene shores of 1800 Atlantic, our vacation house rentals are ideally situated in Key West's most desirable locations.

Why not take a moment to browse our complete selection of properties? Our Key West Vacation Rentals page features our entire inventory, making it easy for you to view all available options. Whether you're looking for a property near the bustling streets of Duval or a quiet retreat by Sunset Marina, you'll find that each of our homes is thoughtfully positioned to enhance your experience in Key West. Start planning your dream vacation by exploring the range of homes available through Last Key Realty today.

88 properties available

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

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)

Baypoint Oasis

Private Home

$255^.00 - $1,312^.00 / per night

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

Monthly Rental

Island Opulence

Private Home

$250^.00 - $876^.00 / per night

4 bedrooms

4 baths

11 guests

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

Bahamian Bamboo

Private Home

$725^.00 - $3,912^.00 / per night

A stay at the DUKE OF CATHERINE is fit for a Queen to bring her King! From the crisp, clean decor to the large hot tub and the spacious master bedroom, the DUKE OF CATHERINE has everything his Majesty could desire. This freshly built, professionally designed home is the perfect size for a weekend rendezvous or an extended stay with the royal family

Duke of Catherine

Private Home

$375^.00 - $2,117^.00 / per night

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

New Property

Fabulously Fresh New Property!!

Monthly Rental

Spirit of Key West

Private Home

$482^.00 - $1,392^.00 / per night

4 bedrooms

4 baths

8 guests

If your idea of a vacation includes pampering yourself and indulging in the finer things in life, then a stay at the DUCHESS OF CATHERINE will be your cup of tea. This newly built, professionally designed home is fit for a King and offers plenty of space for all the members of your court. Located on Catherine Street, just steps from Duval Street, y

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Duchess of Catherine

Private Home

$850^.00 - $5,137^.00 / per night

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

The Poetic Pineapple

Private Home

$165^.00 - $557^.00 / per night

There’s no better way to escape the hustle and bustle of reality than by sneaking off to Key West for a taste of the island life. ELEGANT ESCAPE offers first-class accommodations in a beautiful tropical setting. From the open layout and soaring ceilings of the main house to the enticing private pool and unique guest cottage, ELEGANT ESCAPE has ever

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Elegant Escape

Private Home

$850^.00 - $4,102^.00 / per night

Coordinating the entire gang for a dream Key West wedding, reunion, or simply a vacation of a lifetime is hard enough... let Last Key Realty make the accommodations easy for you. ALL TOGETHER NOW is an entire block of private homes just steps from Duval Street, all yours to enjoy and with everything needed for a large group getaway: a total of thir

All Together Now

Compound

$2,185^.00 - $11,339^.00 / per night

Get the gang together for the ultimate Key West Beach Vacation in a one-of-a-kind giant of an island beach house, BELLE OF THE BEACH. Fully renovated to exceed the highest level of quality and comfort as a large family vacation home, this private estate occupies an entire corner lot, just a block from Smathers Beach. This stilted home allows for a

Belle of the Beach

Private Home

$850^.00 - $4,979^.00 / per night

Get ready to reel in Last Key Realty’s newest vacation home! THE WICKED TUNA is a classic Key West home located in one of the most desirable areas of Old Town. This tastefully restored home features a historic appearance and charm, while offering all the modern conveniences one could desire. In addition to the two bedrooms and two full bathrooms in

New Property

Fabulously Fresh New Property!!

Monthly Rental

The Wicked Tuna

Private Home

$250^.00 - $756^.00 / per night

2 bedrooms

2 baths

5 guests

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

$1,200^.00 - $6,240^.00 / per night

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