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.
144 properties available
SEA BREEZE VILLA is an elegant two-story townhome located in the quiet residential community of Grinnell Gardens, a quaint and intimate community in the middle of Old Town. From this location, you’ll be only a handful of blocks from world famous Duval Street in one direction, and a handful of blocks from Higgs Beach in the other direction. SEA BREE
BAHAMIAN BLUES is a two-story Caribbean-style private home occupying a quiet corner block of Bahama Village, one of Key West's most culturally diverse and vibrant neighborhoods. From this location, you’ll be just two blocks from world famous Duval Street and Key West’s most desirable restaurants, shopping, and attractions. In addition to a prime lo
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
PERFECT HARMONY is a unique one-story home that features an ideal balance between modern touches and tropical styling. With its high ceilings, spacious kitchen, and outdoor lounge beside the pool; PERFECT HARMONY has everything you could desire in a vacation rental. Most importantly, this stylish home includes full-time guest services from Last Key
Throughout Key West you'll find subtle touches of coconuts; from the towering coconut palms nestled throughout the streets of Old Town to folks sipping from fresh coconuts while soaking up the sun, and now, you can add THE TOASTED COCONUT to that list. THE TOASTED COCONUT is a rare gem in the heart of Old Town Key West that captures the essence of
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 BLISS is a historic Key West eyebrow home that recently underwent a complete renovation, and the result is nothing short of pure bliss. This home was designed to combine the best of classic Key West with luxurious modern comfort. SOUTHERNMOST BLISS features 3 bedrooms in the main house and a 4th bedroom in the Guest House, each with it
Does your fast-paced, day-to-day routine have you dreaming of a relaxing vacation in the Florida Keys? KEYSIE DOES IT will turn that dream into reality! This elevated home offers the modern conveniences of newer construction in a gated, waterfront community. In addition to the in-home amenities, you’ll have access to wonderful community amenities a
OLD TOWN OASIS is back! After three years out of the rental program, this luxurious condo has returned, with all the same elegance enjoyed by many guests since 2004, and with many improvements.You’ll be staying right near the ocean in Old Town but with all the quiet and solitude of an exclusive gated community. The Green Parrot (oldest blues bar in
In the same way that the island of Key West has captured the hearts of so many, this charming monthly vacation home will capture yours. ISLAND INSPIRATION combines the appearance and charm of a historic Keys home, with all of the modern conveniences you have come to appreciate. This special home is situated on Margaret Street at the edge of where O
Perched above the sights and sounds of Duval Street, sits TOP OF OLD TOWN, a recently renovated 2-bedroom private home, located within a secluded community in the heart of Old Town. This hidden gem offers a spacious interior, multiple outdoor spaces, and access to the community pool. Combined with Last Key Realty’s Five Star Guest Services & Co
For the ultimate stay in America's Paradise, what could be more perfect for your whole group than AMERICANA TROPICALE? This festive and patriotic home will promise a one-of-a-kind island experience. AMERICANA TROPICALE has 4 spacious bedrooms each complete with its own en-suite bathroom for privacy, a private saltwater pool, a fully equipped kitch
Tell us what you're looking for and someone will contact you with available options.