Key West Luxury Rentals
Welcome to Elegance in Key West: Choose Your Luxury Rental and Book Today!
Experience the pinnacle of opulence with Key West luxury rentals that feature unmatched amenities such as private pools, hot tubs, captivating views, and gourmet kitchens. Every stay with us grants you access to a complimentary concierge, ensuring your Key West vacation is a seamless blend of comfort and indulgence.
Discover luxury in iconic locales such as Historic Old Town, 1800 Atlantic, Truman Annex, and Sunset Marina. For those wanting the city's vibrant energy, our luxury rentals on and near Duval Street await. Please get in touch with us for personalized assistance, direct bookings, or any inquiries.
Group travels become unforgettable with our Key West Compound Rentals, offering two or more adjoining properties. If you're journeying with a furry companion, our pet-friendly Key West luxury house rentals are a perfect match.
156 properties available
SERENITY ON SOUTHARD is a beautifully renovated 1 bedroom second floor condo with a full kitchen and washer and dryer. This condo is located in the Truman Annex, a gated community located in the heart of the island - just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have a peaceful retreat withi
ATLANTIC REFLECTIONS is a newly renovated water view condo that has been meticulously furnished with a modern tropical feel, with spectacular views of the neighboring nature preserve and the ocean beyond, with no end in sight. You'll be able to enjoy those famous Key West sunsets from the living room, and sunrise shadows from your bedroom balconies
Traveling to Key West with a group deserves the ultimate vacation rental home: plenty of space to stretch out and enjoy time together, separate rooms and bathrooms to enjoy privacy, a private saltwater pool and outdoor lounge area, and off street parking for scooters, and of course, bicycles. THE CONTENTED CRANE checks all of these boxes, and more.
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
Get the gang together for the ultimate Key West Beach Vacation in a one-of-a-kind giant of an island beach house, BEAUTY 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
Located in Truman Annex, a gated community with some of the most impressive homes in Key West, this exceptional home stands out from all the rest. NOONA'S MANSION is nestled in a quiet cul-de-sac facing the ocean on a beautifully landscaped piece of property. This impressive home features six spacious bedrooms, a fully equipped kitchen, a stunning
Hidden amongst the thick of Old Town Key West, within Truman Annex, Key West's most exclusive gated community, lives a 'gem' of a home that will surely capture your heart's desire from the moment you lay eyes on it. JASMINE JEWEL is a two-story private home that not only transcends island living at its finest but also offers an ideal location for e
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
TIDEWATER VIEWS is a cozy 820 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out, a residential community with a heated 80-foot pool with large Jacuzzi and Kiddie Pool, tennis courts
On an island where being unique is embraced and the unusual is quite ordinary, lives a home that embodies that colorful spirit. ANGELA’S ECLECTIC GALLERY is a lovingly restored historic home that has been designed and outfitted to include all the modern conveniences paired with exotic and playful touches throughout. Original local artwork and hand-
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
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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