Key West Vacation Rentals: Explore Paradise

Key West Houses and Condos For Rent

Experience the magic Key West, Florida courtesy of Last Key Realty. We offer a curated collection of Key West vacation homes and condos, from charming cottages steps from Duval Street to luxurious waterfront estates with breathtaking ocean views. Whether you're seeking a romantic escape, a family adventure, or a relaxing retreat, our rentals here in Key West can provide the perfect home for your ideal getaway. 


 Immerse yourself in the magic of the Conch Republic. Each of our vacation rentals is meticulously furnished to provide an unforgettable experience. Step outside your door and explore Key West's vibrant energy, from its hidden gems and world-class cuisine to its pristine beaches and lively nightlife. With Last Key Realty, your dream Key West vacation awaits.


Properties Available 145 properties available
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 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)
Sundrenched Reflections
Condo
$170.00 - $494.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (3)
All year long you dream of a getaway to capture that feeling of Key West's ENDLESS SUMMER - carefree days spent tooling around Old Town on bicycles or wandering the island streets in flip flops with the sun warming your shoulders. No plans, nowhere to be, no deadlines - only a to-do list of making memories with your family and friends and possibly
Endless Summer
Private Home Pet Friendly
$675.00 - $4,837.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (105)
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
Star of the Seaport
Private Home Pet Friendly
$1,200.00 - $5,879.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (84)
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 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)
The Poetic Pineapple
Private Home Pet Friendly
$165.00 - $550.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (2)
Spanning an exclusive corner lot in the desirable Midtown neighborhood of Key West is a stunning compound-style home designed as the ultimate vacation destination for a family or group of friends seeking privacy and quiet only a short bike ride or walk from the bustling downtown Old Town area of Key West. In addition to four spacious bedrooms, this
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)
Midtown Mosaic
Private Home Pet Friendly
$260.00 - $914.00 / per night
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (3)
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
Elegant Escape
Private Home
$850.00 - $3,388.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (7)
Resembling a French Plantation, PLANTATION TROPICALE is an impressive island estate that occupies an entire corner block of the desirable Casa East neighborhood of Key West. This expansive property features nearly 3,000 square feet of indoor living space, a separate Guest House, beautifully maintained gardens, and a large private pool and cabana –
Hot HOT 33
Plantation Tropicale
Compound
$1,045.00 - $5,834.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (39)
When your vacation is set around your experiences on the water, where you choose to spend your time on land should be convenient and comfortable. Whether it be a day at the sandbar… reeling in a big catch… kayaking through the mangroves - COASTLINE COMFORT is the perfect place to retire after an epic day on the water around Key West. Located in th
Coastline Comfort
Condo
$200.00 - $1,220.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (89)
SHANG-RI-LA is a term for a utopia designed for life-long learning, happiness and fulfillment. There is no better place to find your happiness and fulfillment than a waterfront oasis on a little island at the farthest Southern tip of the US. This water view condo has been meticulously furnished with a modern coastal feel, with a front row seat to y
Hot HOT 46
Shang-Ri-La
Condo
$222.00 - $1,676.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (149)
SEA CAPTAIN'S HAVEN is an immaculately furnished villa at the Porter Court Complex in Truman Annex, Key West's most desirable gated community, right in the middle of Old Town. At SEA CAPTAIN'S HAVEN, you'll be close to all of Key West's best restaurants and attractions, including Mallory Square and Fort Zachary Taylor State Park.THE LIVING AREA...S
Hot HOT 33
Sea Captain's Haven
Townhome
$315.00 - $1,353.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (22)
SUNSET DREAMS has everything you could want in a vacation home: it is very close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world at SUNSET DREAMS with a large balcony overlooking Florida Bay and the Gulf of Mexico beyond.THE PRIVATE GATED COMMUNITY...Sunset Marina is a gated community
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)
Sunset Dreams
Condo
$170.00 - $499.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (4)
This colorful apartment is all you'll need for your stress-free stay in the Conch Republic. THE MELLOW MACAW is located right in Old Town near the famous Southernmost Point of the United States, two blocks from the Southernmost Beach, and just steps from Upper Duval Street. You couldn't be any closer to the nightlife and attractions of downtown (La
Hot HOT 41
The Mellow Macaw
Condo
$325.00 - $1,432.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 5 (59)

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