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PROPERTY NAME: Villa Riolo 130 Columbus Drive, Islamorada, FLLOCATION: Gated Oceanside House on canalMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 76.5DETAILS: "Villa Riolo" is an updated single family stilt home and perfect...
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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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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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3 Beds/2 bath townhouse in Islamorada, Florida Keys. Ground Floor features a full kitchen, full bath, living room with large tv, dining room with views of the tennis court, outdoor patio with BBQ and additional dining table. Second Floor features a large full bath, 1 king size bed, 1 queen size bed, 2...
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Newly renovated cottage with million dollar oceanfront views.The beautiful in ground private pool will give the serenity you need for a relaxing escape with unobstructed view of the ocean, you can enjoy breathtaking sunsets, watch boats drift by, and listen to the soothing sounds of the waves—all...
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I stayed in the newest cottage . It was very clean and every essential needed. Mark was thoughtful enough to put bottles of water in the refrigerator for us . I had coffee every morning on the upper Tiki...
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Florida Keys Vacation Rentals – Need a private space to call home during your sunny stay in the Florida Keys? Conchy Joe’s is the place! This beautiful home has 3 bedrooms and 2 bathrooms. The interior is fully furnished and decorated in Florida Keys fashion with plenty of space for friends...
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Always enjoy our stays in Keys when we find such a lovely place to have family come to join us. Some homes have a great location some have great amenities, but finding one like this, that has both is...
Distance to beach: 0.5 miles to White Marlin Beach
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*******Check us out on VRBO No. 2003434******** Please go to ....**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.As soon as you walk into this home you will...
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This Lower Keys 6BR/4.5 getaway has a private boat basin and ramp, a pool, and a separate guest house with its own kitchen and living room. Relax in your outdoor oasis at the water's edge before heading out to scuba dive, shop, fish, or even embark on a lobstering adventure.Located on Pine Channel,...
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We have stayed here several times in the past and we had another amazing stay. The house is very spacious.
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*TOP 1% HOME* GUEST FAVORITE* This Key Largo 4 BED/ 4 BA Trendy & Modern Home in Mariners Club is just steps to 2 Oceanfront Pools, Pickleball, Jacuzzis, BYOB Speakeasy Game Room, Tennis & Basketball Courts and Marina. A Coffee Bar, Private Balconies, Instagram LED Photo Wall and private en-suite...
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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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Our Cancellation policy is: Cancellation: If you cancel your reservation in writing 90 days or more before your arrival, you will receive a full refund, less a cancellation fee of $25.00 and Administrative fee. If you cancel less than 90 days before arrival, your payment and any prepaid rent will be...
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We came down from Ohio to get away from the cold weather and had a wonderful time in fandango! We really enjoyed the kayaks, the swimming pool and the hot tub! The house had a wonderful kitchen , hot tub...
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Island Tropical Bungalow! This lovingly maintained, delightful and spacious 3/2 with large expanded porch and Boat ramp just crossing the street makes a great getaway. All utilities are included (water, power, wifi, tv) Large shed in back with laundry (washingmachine and dryer). Totally redone...
Distance to beach: 0.5 miles to White Marlin Beach
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Bring your boat!Nestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. Heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, and two floors facing the canal and a private sanctuary....
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We stayed in this home for a month, the location is amazing if you love to paddle board, kayak and discover the many mangrove islands that are a five minute paddle from your dock. The outside area has...
Distance to beach: 22 yards to Public use + Private views Waldorf Astoria Resort
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This beach view is beautiful and apartment in town can be yours EVEN IF FOR A SHORT VISIT! Just Blocks from downtown Key West? LIKE NO-WHERE ELSE! Like no where else in Key West, do Come + have YOUR, OWN OCEAN VIEWS! Yes! Secluded but not isolated? Yes! Check RATES AS NOW ARE DISCOUNTED, BOOK SOON!...
Featured review
Our stay at the studio was lovely. The proximity to the ocean and beach cannot be beat. The place was very clean, well appointed, comfortable, and creatively decorated too. Our host was very responsive...
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This is one of the most unique homes in all of the upper keys! What makes it special is that it's located on a peninsula so very private while at the same time offers stunning views of the Key Largo Bay.The home was recently updated to include all new flooring, new stainless steel kitchen appliances,...
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Spacious 3-story home with private pool, jacuzzi, terraces, and bright open living spaces.Perfect for long stays, with a full kitchen, fast WiFi, multiple lounge areas, and a quiet backyard. Great location in Key Largo -minutes from Pennekamp Park, nature trails, beaches, marinas and great local restaurants.Ideal...
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Beautiful bright Buttonwood Bay Condo. It's one of the few 2000sf units for rent in the community. No stairs inside the unit. It is a spacious corner unit with a single floor plan. Located close to the tennis courts and pool. From the moment you enter the apartment you enjoy a beautiful view. It's...
Featured review
One of the nicer & classier condos we have stayed at in Key Largo. My wife & I walked around the docks for exercise mostly every day except for a few that were too cold, also spent a few days at the heated...
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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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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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: 3 miles to Sombrero beach
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If you are looking for a tropical Keyz experience, you have arrived in paradise at this three bedroom two bathroom home on a direct ocean access canal which has all the comforts of home and more. **This is a 3 bedroom 2 full bathroom rental** There is no ground floor apartment or access. This is owners...
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PROPERTY NAME: Sandglass 4 74980 Overseas Highway #4, Islamorada, FLLOCATION: Bayside Town House Located in Lower MatecumbeMINIMUM STAY: 7 DaysMILE MARKER: 74.9DETAILS: ONE OF A KIND!!! Magnificent two story townhouse with 5 bedrooms and 3 baths located on Lower Matecumbe in Islamorada....
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Place was super - location decor and views- only issues we had were the a/c did not work well 1st 3 days and we couldn’t sleep in bedrooms even with fans- so the 3 nights we had to sleep in living area...
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Sea Magic on Marlin – Panoramic Open Water Views & Spacious5-bedroom HouseYour Sugarloaf Key adventure begins at this beautifully located waterfront home. Panoramic water views and access allows for boating, swimming, kayaking, snorkeling, and fishing and this 5-bedroom house welcomes...
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PROPERTY NAME: Martin Family Fish Camp 106 Madeira Rd., Islamorada, FloridaLOCATION: 2 Houses Located on a private peninsulaMINIMUM STAY: WeeklyMILE MARKER: 81.9DETAILS: The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each...
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The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove...
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Tropical Paradise has been a popular and romantic vacation rental getaway since 2003. This house includes all the elements you need for an amazing vacation. There are kayaks for adventures, a dipping pool and private beach for relaxation, a floating dock for fishing and docking a boat, (up to 24'...
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The location was exactly what I had hoped. It was secluded, but close to everything. The water views were worth every penny!
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Beautiful canal waterfront stilt home in Key Largo. Home features concrete sea wall and boat lift. Easy access to the Gulf of Mexico and within minutes of the Atlantic Ocean. Amazing fishing and diving spots. The home is completely updated with smart TVs in each room, indoor laundry room, and a fully...
Distance to beach: 2 miles to Founders Park
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*Discover Elevated Island Living at Sea Breeze 41 Luxury 3BR/2BA Condo with Private Boat Slip in Exclusive Coral Harbour Club, IslamoradaWelcome to Sea Breeze 41 — your personal slice of tropical paradise in the heart of the Florida Keys. Nestled within the highly coveted Coral Harbour Club,...
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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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...
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Blue Tranquility will be the perfect destination to get some rest and relaxation for your next Florida Keys vacation. Located directly on the ocean side of South Pine channel, which offers wonderful sunrises and moon rises. Kick back and enjoy the balmy breezes on the serene screened in porch. The pool...
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The Heart of StoneIs a canal and pool front elevated keys home with 2 bedroom and 3 bath with plenty living, lounging and entertaining areas. The home has been recently completely renovated and refinished. The home boulsters an open floor design with 2 balconies (canal/ocean/pool view) in both the...
Featured review
We stayed at this beautiful home, in a perfect location, during the months of March and April 2025. It is a home away from home with all the necessary comforts. It is situated on the canal and steps away...
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If you want to experience the true meaning of a Key Largo Island vacation, then look no further than our spacious townhouse on the ocean side of the world-famous Key Largo, Florida. ... The Dive Capital of the World! This Villa is located inside Kawama Yacht Club, a beautiful Hawaiian Island style resort...
Featured review
Nice condo in Key Largo. Owner very responsive. Beds comfortable. Would rent again, for sure. Close to a lot of restaurants & stores.
Distance to beach: 2 miles to Sombrero Beach
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A beautiful waterfront half duplex home in a tropical setting with views of the Gulf of Mexico and incredible sunsets. Recently renovated octagonal shaped home with wide open water views from every window. Newly furnished comfortable interior with all the amenities you'd expect. Brick pavers surround...
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We have rented Brian A for the last 3 Januarys to escape the cold north. The location is wonderful because we like the 4 mile walk around the airport. We enjoy the heated pool and the occasional manatee...
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PROPERTY NAME: Twice the Charm 214 S. Ocean Shores Dr, Key LargoLOCATION: Oceanside Canal Front HomeMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 98.5DETAILS: "Twice the Charm" is a gorgeous newly remodeled single family...
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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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Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and...
Featured review
Our family has been traveling to Islamorada for Spring Break for the last 4 years and this was by far our favorite place to stay! Our family enjoyed the private oasis that the townhome provided. We felt...
Distance to beach: 4 miles to Founders Park
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Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air...
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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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Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking...
Featured review
This condo was very conveniently located. We could snorkel at John Pennekamp and kayak the mangroves of Islamorado. Plenty of close good seafood restaurants in vicinity. Spend the day at Bahia Honda.
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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: 3 miles to Bahia Honda Park
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Modern 4 bedroom 2 bath stilt home centrally located in Big Pine. Heated salt water swimming pool. Corner canal front lot with 120 ft of dockage. 5 min. to the Gulf and 10 min. to the Atlantic. Close to the Winn Dixie grocery store. Free public boat ramp 5 min away. Room on property to park 6+ cars...
Featured review
Well, we think the house is very nice and clean. Great location, lovely neighbors nice quiet place we have only positive things to say and nothing negative so have a great day
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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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This charming 2-bedroom, 2-bath rental home is perfect for your tropical getaway! With a minimum stay of 28 days, it accommodates up to 6 adults and 1 child, making it ideal for families or groups. The master bedroom features a king-size bed, while the guest bedroom offers a queen-size bed. Additional...
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Enjoy breathtaking sunsets on the private beach while staying in this beautifully remodeled corner unit. The unit was completely gutted in 2021 and features 2 bedrooms plus a built out loft and 3 full bathrooms.The unit has a huge master with a king bed plus a bathroom/walk-in closet and...
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We stayed at this location in April-May 2026. It was amazing. My parents stayed with my husband and I and our 10 year old son. The unit was immaculate. It was clean, beautiful and fully equipped for our...
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
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...
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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Clean, Tropical 3/2 on open canal in quiet residential neighborhood on a cul-de-sac. House is on Gulfside with quick access to Miles Channel Bridge towards ocean or bayside. 50’ concrete dock with fish cleaning station.Master Bedroom has a queen size bed, shower and indoor jacuzzi tub. Second...
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Alex and I had a wonderful time in your beautiful home. Loved eating dinners (breakfast and lunch too!) sitting outside. Peaceful and lovely. The storage room downstairs was perfect for storing all our...
Distance to beach: 10 miles to Bahia Honda
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Welcome to Paradise Palms! This amazing 3 bedroom home on Cudjoe Key is perfect for your next Florida Keys vacation! Tropical landscaping surrounds an inground pool that overlooks a beautiful canal...everything you could want and more! There is also large concrete dock for your boat, quick easy ocean...
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My family and I stayed for the month of June 2022 and this was the first time we had visited Cudjoe Key. The house was beautiful and VERY clean. The kitchen was well equipped with everything you needed...
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