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49 properties available
This Old Town condo is perfect for anyone who can't get enough of Key West's famous nightlife scene. CASITA ANGELITA is located right in Old Town, half a block away from Duval Street and smack dab in the center of the entertainment district. You couldn't be any closer to the late-night scene and attractions of downtown. Fair warning... It can get
DOCKSIDE DAYDREAMS is a tastefully decorated villa located in the Coconut Mallory Resort & Marina with two large community pools with plenty of chaises. There are also boat slips available on-site for rent if you want to bring your boat.THE LIVING AREA...This modern home has just undergone a complete renovation to a very high standard. No expen
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
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
THE BEAMING BARRACUDA is a freshly renovated townhome located within Truman Annex, Key West's most exclusive gated community. You’ll be within walking distance to all that Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to its excellent location, THE BEAMING BARRACUDA provides an open living area and outdoor co
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
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
Don't miss an exceptional opportunity to spend your Key West stay on the grounds of an incredible estate property in the most ideal Old Town location you could imagine. DARLING OF DUVAL is a two-story guest cottage that offers many of the essentials and comforts of a luxury hotel plus the added benefits of an in-home washer & dryer, a private p
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
NATURE'S EDGE is a well maintained condo that is located at 1800 Atlantic Blvd on the beach, just steps from the ocean and sand in your toes. You'll enjoy peace and quiet on your balcony, with the Key West Nature Preserve just outside your door. NATURE'S EDGE is located in an upscale private community within walking or biking distance to all of you
ANGELFISH REEF is a stylish townhome featuring a tasteful abundance of local art and flavor located within the Truman Annex, Key West's most exclusive gated community. You’ll be within walking distance of everything Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to its excellent location, ANGELFISH REEF provid
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
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