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The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment * King size bed in the bedroom *accommodates 2 adults only * WiFi inlcuded * Parking included *Central AIr Conditioning * Check-out cleaning is $160 * This is not a hotel; it is a privately owned condo facing the...
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Just finished a 2 week stay and I have been renting from Pam for over a decade and she continues to make a great condo even better with her constant upgrades to the unit and she is a wonderful host. The...
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...
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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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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
Wonderful home, amazing response for any needs, great pool and parking. The covered porch (lanai) expanded the living space. We had an all around great experience. We will be back in the future!
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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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...
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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...
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...
Featured review
Fabulous location, great host. Awesome little getaway just big enough for two. Pam is great to work with.
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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...
Distance to beach: 2 miles to Smathers
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28 minimum nights required by city of Key west. New listing-One level home! Relatives have stayed and loved it. Rates: October $9,000, November is $16,000 /month, December $18,000/month, January, 2027 $21,000/month, February $23,000/month, March $23,000 per month, April, 2027 $17,000 per month, cleaning...
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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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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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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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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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Atlantic Sunrise – 3BR/3BA Penthouse with Partial Ocean ViewWelcome to Atlantic Sunrise, the only 3-bedroom, 3-bath unit in the exclusive 1800 Atlantic complex. Spanning approximately 2,000 square feet, this spacious penthouse comfortably accommodates up to 8 guests, making it the perfect retreat...
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Enjoy the ocean views from this beautifully appointed condo in the exclusive Key West Beach Club.This two-bedroom, two and half-bath waterfront condo that has been newly renovated with casual furnishing and all the comforts of home: central air conditioning, cable TV, washer/dryer, Wi-Fi, and a fully-equipped...
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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...
Featured review
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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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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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 glass slider doors that invite in mother nature's hues. Full...
Featured review
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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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...
Featured review
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...
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,...
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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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Luxurious Renovated Monthly Rental at 1800 Atlantic – Ocean Views & Premium Comfort Step into elegance at this beautifully renovated, high-end condo at 1800 Atlantic. From the moment you enter, you'll appreciate the meticulous attention to detail and modern upgrades throughout the space. Enjoy...
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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...
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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: 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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Lady Grace will not be in Florida for the 2025-2026 season. Come visit her in the BAHAMAS!Bahama Cruise with exploration in the Exuma IslandsFor guests who want to enjoy a vacation on the move, our cruise aboard Lady Grace is for you. Nassau, Bahamas is the center of our winter cruise program,...
Featured review
The Lady Grace was awesome and Kelly and Capt Jamie were phenomenal. Everyone loved the yacht and everything she had. Plenty of beds bathrooms and gathering places. The sunset cruise was excellent and so...
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