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.
149 properties available
TURTLE COVE VIEWS is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home through the large windows or from your covered porch, with outdoor dining. The private 35-foot boat slip offers easy access to the beautiful waters of the Florida Keys and the home com
Located across the street from Blue Heaven, above the delicious La Creperie French Cafe, sits THE PIRATE’S PENTHOUSE. This hidden gem is ideally located in the heart of Bahama Village and within walking distance to everything Duval has to offer. THE PIRATE’S PENTHOUSE has touches of maritime decor sprinkled throughout this spacious condo, complet
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
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
Key West is known for all things lime: Key Lime Pies, Margaritas, and now, THE ZESTY LIME, a rare gem in the heart of Old Town Key West that captures the essence of classic Key West in a completely renovated modern design. THE ZESTY LIME includes all of the coveted amenities of a vacation home: a spacious living area, an ideal bedroom and bathroom
When exploring Old Town Key West it is typical to stumble upon a surprise tropical bloom that reminds you of the magic of the island you have found yourself on. At the right time of year when enjoying the private garden of this townhouse, you may look up into the trees and spot a bunch of bananas smiling down on you. BANANA BLOSSOMS surprises you w
SOUTHERN STAR is a modern Key West home nestled in the quiet Meadows neighborhood of Old Town that combines the island way and the sweet life of the South. With wide porches, a breezy interior, cathedral ceilings, and an apparent southern charm, it's easy to see where this home gets its name. In addition to its distinct southern features, this home
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.
In the Historic Seaport area of Old Town, there is a house that will behold your eye. At first glance you'll see that HEAVENLY ZEN is beautifully maintained with carefully tended landscaping; however, nothing will prepare you for what is inside. As you walk in, you will feel an immediate sense of peace and relaxation. All of the spaces in this meti
As if a vacation to the Florida Keys wasn’t memorable enough, the million-dollar views from INFINITE HORIZONS are ones you’ll never forget. Located about 10 minutes north of Key West on Big Coppitt Key, INFINITE HORIZONS sits on an oversized, open water lot with a private pool and beach placed against the stunning backdrop of the gorgeous Gulf of M
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
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
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