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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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Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.As...
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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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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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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The Mile Zero House is a MONTLY VACATION RENTAL. Rent one or more months comes completely furnished. Charming conch home with true Key West character. Fenced for privacy with a open style front porch to enjoy the local flavor along with a passing Conch Train. Full size kitchen that is nicely stocked with...
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Historic Conch House Located Downtown Key West near Duval St and restaurants beach and many attractions ! Private Yard fully locked and fenced with beautiful plants Sitting on the front Porch you feel...
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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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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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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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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Beautifully Renovated 2BR/2BA Condo at Exclusive 1800 AtlanticExperience comfort and elegance in this beautifully renovated 2-bedroom, 2-bath condo located in the prestigious 1800 Atlantic community. Each bedroom features a king-size bed, generous closet space, and direct access to a private balcony...
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Location,Location, Location!! Old Town cottage!! Great location! 2 bedrooms 2 full bathrooms, Both bedrooms have King beds and french doors to outdoor sitting areas. Great front porch to watch the conch tour train go by.
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Welcome to “The Coconut” – Your Slice of Old Town ParadiseTucked into the heart of Old Town Key West, The Coconut is your dreamy island hideaway — where history meets laid-back tropical living.Built in the late 1800s and full of classic Key West charm, this sun-drenched...
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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Welcome to the cutest little Conch Cottage in the Florida Keys! Located in the Seaside Resort Community, only ten minutes to Key West! You won’t find a more affordable and comfortable location than this! The resort has not one, but two large pools, one that overlooks the open water! Other amenities...
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Pool & Jacuzzi Resurfacing NoticePlease be advised that the pool and jacuzzi area will be closed for resurfacing beginning: July 6th – August 30th (weather permitting)The entire pool and jacuzzi area will be fully closed off during this time to allow the contractor to safely complete...
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...
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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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When they say it's all about the location, this home says it all!By city ordinance, you must rent this property for 29 days or longer!!Welcome to this beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street.A stairway decorated with wainscoting will lead you...
Distance to beach: 0.8 miles to Simonton Beach
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AboutClassic Old Key West HomeThis home offers a rare combination of location, charm, and character. With a beautiful mix of historic details and modern updates throughout, it’s perfect for couples traveling together or anyone hosting visitors during their stay in paradise.Primary guest...
Distance to beach: 0.5 miles to South Beach
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This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $90 *Cleaning fee of $100 is additional. * WiFi included * King size bed * Outdoor table and two chairs * spacious shower * excellent location for walking Old TownThis accommodation is the perfect...
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This property is perfect for a couple or a single wanting a getaway to the vibes of Key West. It has everything you need from a comfortable bed, a cool air conditioner, a functional kitchen with all the...
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Welcome to your Key West escape! Nestled in the heart of 'Old Town', this charming townhouse is part of a wonderful twelve townhouse community with a lush, tropical garden courtyard that provides a tranquil, resort-like feel. You're just a half-block from the quiet end of Duval Street,...
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Welcome to Parothdhideaway, where it’s always Five O’clock! Less than 10 minutes’ walk from Duval Street you will find this tropical island getaway. Find yourself on island time yet still having every amenity at your fingertips like a soaking pool hidden under the trees on the large...
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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...
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TRANQUIL BEAUTY: 3 BR’s, 2 Baths Private Haven paradise with huge private heated pool and landscaped back yard!ENJOY KEY WEST at its peaceful best in your 3BR, 2 bath private hideaway in a quiet neighborhood near Higgs and Smathers beaches and only a 10 minute bike or Uber ride from Duval Street....
Featured review
Location was great. Quiet neighborhood, lush garden and good accommodations. The tile in the pool is excessively dirty. Pool guys came several times during our stay and never cleaned them.
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