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Beautiful Ocean Beach and Pool view from the deck. Relax in paradise where everything is steps away! Suntan on the white sand beach complete with chairs, tiki and palm trees! Spectacular sun sets!Condo is townhouse style with stairs to bedrooms. Master bedroom has king bed with full private...
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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 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 $120 * This is not a hotel; it is a privately owned condo facing the...
Featured review
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...
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Welcome to Barracuda Bungalow in Big Pine Key! This quaint ground level home is reminiscent of old Florida Keys with some new and improved upgrades like the brand new inground pool and spa. If you’re looking for that laid-back island feel, in a nice quiet neighborhood where you can watch the key...
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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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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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Escape to Key Largo and experience the ultimate Florida Keys getaway! Whether you're looking for a family vacation, a trip with friends, or a peaceful retreat, this newly remodeled 4-bedroom, 3-bathroom home offers the perfect setting to relax, explore, and make lasting memories.Key Features:Spacious...
Featured review
We stayed in this home for a month and we had a wonderful time. The home is very spacious with 4 bedrooms and 3 bathrooms. It is remodeled and it has 2 family rooms. It had space for my boat and parking...
Distance to beach: 5 miles to Bahia Honda State Park
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Welcome to your very own “Island Escape”! This beautiful home is located in one of Big Pine Key’s most favorable boating neighborhoods with quick ocean or gulf access for most any size boat. It’s only a few lots in from open water! The large 75’ concrete dock offers plenty...
Distance to beach: 2 miles to Founder's Park
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Long-term rental available in the beautiful Venetian Shores community of Islamorada, Florida. This 3-bedroom, 2-bath home sits on a secluded plugged canal by the water. Enjoy a large master bedroom, a spacious open layout, and a generous outdoor deck ideal for entertaining. Additional features include...
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“Endless Paradise” is truly a Cudjoe Gardens gem! This ground level (no stairs here!) vacation rental home is walk in and relax ready! Located in the highly desired Cudjoe Gardens neighborhood known for its great boating access, ground level prestigious builds, local marina and don’t...
Distance to beach: 0.1 miles to At Kawama Yacht Club
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Enjoy Key Largo - A Year Round Vacation Paradise *** Short Term Rentals Available**** * * NO PETS * * *NO PETS * * *NO PETS * * *. - the Associate does not permit renter's pets!!!* * * SPECIALS LISTED HERE WHEN AVAILABLE * * * RATE REDUCED - March 7 - 11 (4 nights) Inquire...
Featured review
We have stayed in Kawama yacht club several times over the years. This is our second time in this particular condo. Everything you could possible need is in this condo. Another huge benefit is if there...
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Please be advised that the building elevators will be out of service for modernization from April 27, 2026 through, June 19, 2026. During this time the elevators will not be functional — all guests and visitors must use the stairs.Beautiful top floor ocean front 2 bedroom 2 bath condo at La...
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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CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...
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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...
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,...
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CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...
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Welcome to the Snow Grouper, a classic and comfortable vacation rental home in the much sought after Summerland Cove on Summerland Key.This two-bedroom, two-bathroom home is completely remodeled, with a layout that is welcoming, from the open concept kitchen and living room, to the beautifully furnished...
Distance to beach: 0.5 miles to Key Colony Cabana Club Beach
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Beautiful 2-story half duplex home on wide canal with boat slip. Sleeps 10 comfortably. 4 bedrooms, bathrooms and lower-level family room with mini kitchen make this a great place for multiple families to have private space or gather together.Plenty of parking for boat trailer and multiple vehicles,...
Featured review
Rare find of 4 full baths and 4 real bedrooms (not a daybed stuck in a sunroom like some rentals market as a bedroom). House comes with everything you need - beach towels, coffee maker, toaster, blender,...
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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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Welcome to "Sol y Sal" in Buttonwood Bay. Brand new 2 bedrooms + den/ 2 1/2 bath townhouse. This unit was just redone in 2024 and includes fantastic, high-end finishes. Spacious living room with 70 in. tv, dining room with seating for 8, and kitchen with stainless steel appliances, and powder...
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Welcome to Croton Lane Retreat! This comfortable home is located on a canal with 2 bedrooms (Queen beds) and 2 full bathrooms. It has a beautiful screened-in porch with comfortable seating for relaxing and an outdoor dining table with seating for 6 for comfortable outdoor dining. The house has central...
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...
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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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Available for the 2026 season! (weekly rentals permitted) Affordable piece of paradise! Escape the cold and come enjoy this Venture Out home with open concept, bright and airy rooms, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you’ll be amazed. This fully furnished home...
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Welcome to San Remo Retreat, a very unique property located in the highly desirable Doctor’s Arm neighborhood on Big Pine Key. Bring your boat, plenty of dock space here! The fish cleaning table will hold your biggest catch of the day!You will feel right at home in this very nicely decorated,...
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PLEASE INQUIRE WITHIN FOR ALL STAYS AND SPECIAL DEALS!!!OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access. This Open Water home HAS IT ALL. -Brand New (Sept 2017) Huge, heated...
Featured review
Great location! Sunrises and sunsets were amazing. Easy location to open water, kids loved going out on boat. Fishing right off the dock. Lots of wildlife. Everyone loved the outdoor bathroom! Very convenient....
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Large, very spacious, beautifully appointed 7 BR home with breathtaking ocean views, large dock, pool, 2 jacuzzis, BBQ grill, 4 kayaks, large tiki, two fully equipped kitchens, all new appliances and major upgrades since Irma. Comfortably accommodates multiple families. Very private and secure with property...
Featured review
We loved our stay at Casa Lorelane! We had 18 people and never once felt crowded. The living area on the second floor was amazing. The second kitchen on main floor made it easy to prepare food to enjoy...
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This beautiful waterfront home was recently updated and features 3 bedrooms with a spacious master bedroom and 2 bathrooms. The home has a very large kitchen with an island and two refrigerators. The kitchen is fully equipped with pots, pans, utensils, plates and more. We also provide a coffee machine...
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PROPERTY NAME: Moon Bay A410 104350 Overseas Highway, Key Largo, FloridaLOCATION: Bayfront CondominiumMINIMUM STAY: WeeklyMILE MARKER: 104.3DETAILS: This 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and...
Distance to beach: 7 miles to Sombrero
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Great news, we just completed construction of a brand new 60FT dock. We have a kayak launch and plenty of room for your boat.Our indoor upgrades included getting a Tempur Pedic king-size adjustable bed for the master bedroom (raise the head or feet). All the TVs are now 4K smart TVs, which we mounted....
Featured review
This house has the latest and greatest of everything. It's beautifully decorated and located on the best part of the island. Over looking a heated pool, it's steps away from an elevated observation deck...
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*TOP 1% HOME* GUEST FAVORITE* This Key Largo 4 BED/ 4 BA Trendy & Modern Home 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 baths await...
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Welcome to Turtles Nest! A beautiful 2-bedroom 2 bath condo in the heart of Marathon complete with 40' boat slip and a private boat ramp! 30 steps to the water and heated pool, this 2/2 condo is ready for your changes in attitudes, changes in latitudes!Community/Location: - beautiful canal-front...
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Welcome to Margarita Manor – Your Tropical Escape in the Florida Keys!Set your watch to island time and relax at Margarita Manor, a vibrant waterfront oasis perfectly suited for sun-chasers and boating enthusiasts alike. Located just moments from open Atlantic waters, this breezy retreat offers...
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Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs...
Featured review
Love Beacon Reef and the unit was very comfortable and well equipped. Very close to the pool and the staircase from the balcony was convenient
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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: 88.5DETAILS: "Twice the Charm" is a gorgeous newly remodeled single family...
Distance to beach: 0.3 miles to Sunset Park
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This beautiful, modern and stylish home is perfect for families and group vacations. It features high quality and modern furniture and beds, a fully equipped kitchen, high-speed wireless internet and a private, heated pool.This is the lower half and if you book a reservation, there WILL NOT be people...
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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...
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This pet-friendly home completed in 2012 has 5 rooms, 3 king-size beds, and 4 twins plus a twin sofa bed and three full bathrooms. The home has a huge kitchen with custom made wood cabinets and top of the line stainless steel appliances including an indoor gas grill and a standing freezer: to keep the...
Featured review
SIX STARS * * * * * *This is a wonderful home with channel access right behind the house. It's perfect for the whole family, very spacious. The owners are very accommodating, making sure everything...
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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...
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Coastal Themed Villa Retreat in Paradise Awaits for You! Spacious Large Open Floor Plan on 2nd Floor with large Family Room and 2 Large Bedrooms each on opposite sides of the unit. Large Open Kitchen to Family and Dining Area...Bathrooms are also Coastal Themed. Villa is quiet and peaceful surrounded...
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Welcome to Buccaneer Boathouse! Pack your floral shirts, swimming gear and sandals and come on down to Little Torch Key in the beautiful Florida Keys. This lovely home is spacious with 2 bedrooms and 2 bathrooms. It offers a large open kitchen, dining and living area for everyone to hang-out and plan...
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This relaxing retreat is situated in a very private part of Port Pine Heights on Big Pine Key. Great boating, fishing, and snorkeling can be easily accessed, just a short boat ride down the canal to Pine Channel. There is plenty of space to park your boat on the concrete dock and clean your catch on the...
Featured review
We thoroughly enjoyed our stay at Palmetto Retreat. The home was spotless and had all the amenities we needed. A couple of menial things didn't work, and Christine (Rudy) took prompt care of them while...
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An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most...
Featured review
We have been spending time here for 11 years now. Love our summer stay at your cozy home. Thank you for letting us make great memories here
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PROPERTY NAME: Marlin House 156 Venetian Drive, Islamorada, FL 33036LOCATION: Bayside Canal home located in the popular Islamorada neighborhood of White Marlin BeachMINIMUM STAY: 90 days, this is a 3 month minimumMILE MARKER: 74.5DETAILS: You will love this charming and cozy Keys Holiday...
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Multi-million dollar views and the peace and quiet you expect in the Keys. This completely renovated condo has direct views of Florida Bay throughout, and the property includes white sandy beaches, a clubhouse with a new gym, sauna, and firepit. The property also boasts a swimming pool, bocce, basketball,...
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Looking for the perfect getaway for your Florida Keys vacation? Look no further! Tropical Oasis is just the home for you and your guests with only 23 miles to Key West; not that you’ll ever want to leave the beautiful views of the mangroves and sea-life!Tropical Oasis is a two bedroom, two bath...
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Best Deal in Truman Annex – Céad Míle Fáilte! 2 Bedroom | 1 Bathroom | Sleeps Up to 5 GuestsWelcome to Innis-free, our little slice of paradise in Key West—where you're greeted with Céad Míle Fáilte, an Irish expression meaning “a...
Featured review
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...
Distance to beach: 0.0 miles to Inch Beach - Just a 3 minute walk
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Note!! ALL Reservations are accepted on a "Saturday to Saturday" check in/Check out basis.Casa Mar Azul II is a charming 2 Bedroom, 2 Bath 1/2 Duplex (Sleeps 2-5) located at 12 7th Street directly across from the Key Colony Beach Golf Course with a great view out back of a 200 foot canal....
Featured review
We were looking for a place in the keys to dock our boat while enjoying all the Keys has to offer. The casa was well appointed for anything you might need in the kitchen including crock pot and blender....
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Hi, nice to meet you!!! If you like to be somewhere surrounded by a magnificent peace and balance, fresh, organized and a very clean home, "you just found it". You will be happy to go out in the boat and come back to a relaxing home to enjoy the rest of the day with family or friends with...
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Aaarrrghhhhhhh MATEY! Florida Keys Vacation Rentals – Looking for a perfect sunny get away in the beautiful Florida Keys? Blackbeard’s Bounty is just the place for you and your guests!This tropical oasis is located on Little Torch Key and is only 28 miles from Key West. Situated on a wide...
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The South House is a superb vacation home on Summerland Key. It offers everything you need to make your Florida Keys vacation truly memorable.The downstairs pool area is private and serene. There are several lounging areas to enjoy suntanning or wonderful afternoon shade. The crystal blue pool is...
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