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Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park
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SUMMER/FALL SPECIAL. $500 OFF MY RATE. So welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My oversized two-bedroom, one...
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A touch of Cuba was the perfect little spot. We are now spoiled to the conveniences of renting direct with the owner, having Class A rated efficiencies, Beach, Bikes, Pool, very quiet and well kept area...
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Tom's Oceanfront PenthouseExperience coastal luxury at Tom's Oceanfront Penthouse, a stunning 3-bedroom, 2-bathroom unit ideally located in a prime spot within the complex. Just steps from the elevator, this expansive 2,000 sq. ft. penthouse offers the ultimate in comfort and convenience,...
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We went to Key West to attend my nephew's high school graduation. People extremely hospitable and easy to work with to reserve the condo. Comfortably fit 5 adults. The room, views, and landscaping are beautiful!...
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Spacious 2-Bedroom Condo with Ocean Views & Island ComfortsThis beautiful 2-bedroom, 2-bath condo offers a lovely view of the Atlantic Ocean and an extra-large floor plan with a slightly oversized private balcony—accessible from both bedrooms and the living room. It’s the perfect island...
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Shipyard Pool Closure The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. We expect the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026.Best Deal in Truman Annex – Céad Míle...
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We really enjoyed the unit at Shipyard Condos. Very clean and well equipped. Walking distance to local restaurants and very convenient with a dedicated parking place. Pool was nice too. There were only...
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Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and travels of “Papa” Earnest Hemingway. This is a beautiful top floor two-bedroom ocean-view unit at 1800 Atlantic condos. It has pristine ocean-views from all rooms...
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BEST PLACE WE EVER STAYED AT. THERE WERE FOUR OF US. BEAUTIFUL LOCATION. SO COMFORTABLE. KIRK WAS SO HELPFUL TO HELP US GET SETTLED IN. ALL THE TREATS OF HOME. VIEW INCREDIBLE. WANTED OUR TIME THERE TO...
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Historic 2-Bedroom Cigar Maker’s Cottage – A Key West Gem!Step back in time and experience Old Key West charm in this delightful 2-bedroom Cigar Maker's Cottage, built in the 1880s. Nestled at 1008 Whitehead Street, the cottage sits just across from where a bustling cigar factory...
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This nicely appointed home is located in Key Haven subdivision of fine homes. It offers an expansive living room with upgraded kitchen and appliances. The kitchen is nicely stocked with plenty of room for multiple cooks. The house can accommodate up to six people with 3 bedrooms and 2 full bathrooms....
Featured review
We absolutely love this home! The interior features plenty of space and storage. The kitchen is well equipped with everything you need and more. The bedrooms very comfortable. The shower in the master has...
Distance to beach: 0.4 miles to Fort Zachary
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Escape the winter and settle into this beautifully renovated 2-bedroom, 1-bath condo in the heart of Old Town Key West — perfect for snowbirds and monthly renters seeking the ideal balance of tranquility and convenience. Located in the prestigious gated community of Truman Annex at the Shipyard...
Distance to beach: 2 miles to Smarthers Beach and Higgs Beach
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This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and conveniently located on the Island. This home welcomes you with a white picket fence! It has been nicely upgraded down to the wood floors and crown molding trim. Open living room and dining...
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Sunshine House on Harris Street, Key West is a Home away from Home. We enjoyed 2 months of comfort and convenience at this home. The home is furnished with tasteful Island Decor. The layout is 3 bdrms...
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OFFERING A REDUCED RATE FOR JULY AND AUGUST DUE TO POOL RENOVATION. Sammy's Hideaway is located in a gated community with easy beach access. This 2 bedroom/2 bath condo faces the Atlantic Ocean offering wonderful ocean breezes and an oversized balcony with dining set. The open style living room has...
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We stayed at 102 S at LaBrisa for Halloween. The apartment was clean and absolutely gorgeous. The view of the Atlantic Ocean was breathtaking. The pool was clean with warm salt water. The grounds were very...
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Mar Y Sol – Luxury Oceanfront Condo in Key West Breathtaking Views. Unbeatable Comfort. Perfect Location.Welcome to Mar Y Sol, a stunning oceanfront condominium located at 1800 Atlantic, Key West. This beautifully renovated 3-bedroom, 2.5-bathroom vacation rental offers sweeping views of the...
Distance to beach: 2 miles to Smathers
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January-April 2027 is booked. December 1-29 is available along with the rest of 2026. 28 minimum nights required by city of Key west. One level home! Relatives have stayed and loved it. Rates: July-Sept 8k per month, October $10,000, November is $20,000 /month, December $22,000/month. January, 2027 $23,000/month,...
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Coral Hammock – 3BR/3BA Home with Pool Views in Coral Hammock3 Bedrooms | 3 Full Bathrooms | Sleeps up to 8 | Backs to Community PoolWelcome to Coral Hammock, your home away from home in beautiful Key West! Built in 2004 and meticulously maintained, this spacious 3-bedroom, 3-bathroom home...
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Our family had a wonderful time staying in this townhome style rental. We relaxed and enjoyed the views of the bay and marina from the back porch. The boat slip worked great for our rental boat. This...
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Welcome to Moveable Feast, a dreamy home in the heart of Bahama Village that sleeps 10 comfortably. Located on a quiet, friendly lane with two parking spaces right in the middle of all the action. Four bedrooms (one king and three queens) - each with their own attached bathroom - plus a half bath on the...
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Charming Pool Cottage in the Heart of Old Town Key WestPerfectly situated in historic Old Town Key West, this quaint and inviting pool cottage offers the ideal island escape for a couple, with room for occasional guests. Thoughtfully decorated and impeccably maintained, the home features a newly renovated...
Distance to beach: 0.5 miles to Simonton Street Beach
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Welcome to the Dancing Rooster, your charming retreat just 2 blocks from Duval Street in the heart of downtown Key West! Nestled within the historic Simonton Cottage enclave, our recently renovated 3-bedroom, 2-bath home offers the perfect blend of comfort and convenience. You’ll be surrounded by...
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Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second floor...
Featured review
I have not stayed there yet, but will gladly take $5 for this review. I hope is as nice as it its described
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Beautiful top floor ocean front 2 bedroom 2 bath condo at La Brisa in Key West. The property has a queen bed in each bedroom and the master has an en suite bathroom. Totally renovated Kitchen and a balcony with amazing Sunrise Views across Smathers Beach. The living room has a flat screen smart TV...
Featured review
Very thing was good the condo was perfect and the pool was great the parking was close to the elevator
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Available starting July 1, 2026. Extremely rare for Key West: Oceanfront property with dock and swimming pool. Have your cake and eat it too! 10 minutes to famous Old Town and its many entertainments, or to luxurious Perry Hotel and Marina, or to famous Safe Harbor Marina with Artists studios and Hogfish...
Distance to beach: 0.4 miles to Fort Zachary Taylor State Park
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Key West is just like the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street and Zachary Taylor Park ( do yoga on the beach, swim, snorkel, or hang hammocks between the palms). Walk to shops, restaurants,...
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Luxury island resort style living in Key West. 1800 Atlantic offers a private sandy sunning beach, Olympic style pool, gym, three tennis courts (one is clay), fitness center, community clubhouse, picnic areas and more. This condominium is updated and turnkey . Open living and dining spaces, eat-in kitchen...
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Very good location in Big Pine, deer paradise, a very quiet place to relax and rest if what you want is incredible peace to relax, believe me, this is your place, lots of outdoor space, the house is on a corner, very cozy inside and out, outdoor hammocks, many places to sit and spend a lovely afternoon...
Distance to beach: 300 feet to Southernmost Beach
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This beautiful one bedroom, one bath condo is located in the Historic District, Old Town Key West . The condo is approximately 50 feet to Duval Street. It sleeps up to 4 people, one bedroom with a queen bed, a sleeper sofa in the living room which sleeps 2. One bathroom with a stand up shower and...
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