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Holiday Rentals in Florida Keys, FL

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    Travellers to Florida Keys are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    2 BedroomsSleeps 6Quick View
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    5 of 5 bubbles
    2 Reviews
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    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 of 5 bubbles
    2 Reviews
    3 BedroomsSleeps 8Quick View
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    Please contact us if you have any policy questions since we do not agree with this website forcing us to choose policies they dictate. We have our own polices so please ignore what's posted in the policies section on this website. Beautiful three story luxury home in the heart of Islamorada the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 of 5 bubbles
    16 Reviews
    3 BedroomsSleeps 6Quick View
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    This beautiful CBS construction- three bedroom / two bath home is located in a private, gated community with only 32 homes and has been completely renovated with new baths and kitchen, including granite counters and stainless steel appliances in a beautiful kitchen that opens to the dining and...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    4 Reviews
    1 BedroomSleeps 2Quick View
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    Solaris Cottage, located on one of Key West most private slow lanes, was built for you. We guarantee that the moment you step onto the front porch and into the cool, sun-dappled living area, your stress will drop away and your creativity will soar. This one-bedroom, one-bath unit is located on a...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4.5 of 5 bubbles
    7 Reviews
    2 BedroomsSleeps 8Quick View
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    About this property
    This truly tropical retreat Keys’ home has an open floor plan, vaulted ceilings, and modern open kitchen. Master Bedroom has king sized bed, full bathroom with shower, granite sink, walk in closet, glass block windows. Second Bedroom has queen sized bed, closet, and adjoining bathroom with...
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    Marathon, Florida Keys 33417
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    About this property
    Welcome to Duck Key Vacation Rentals! Located on a private island in the Florida Keys, our Duplex is the perfect spot for your next vacation! Within walking distance, you’re only minutes away from many outdoor activities like fishing, diving, snorkeling, dolphin encounters, sailing, parasailing,...
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    Lower Keys, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 BedroomsSleeps 4Quick View
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    Relax in this two bedroom, one bath tropically colored vacation home. This home has just been fully remodeled. Lots of windows give it a bright spacious feel. Fun colors and decorations add to its tropical ambiance. Large living room dining area with windows on two sides. Sleeper sofa, rocking...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Take a dip in our gorgeous new pool, or jacuzzi (for 14 people)! Ocean Pointe Suites in Key Largo is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. The suite offers a...
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    Tavernier, Key Largo 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • Balcony
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    Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    4 of 5 bubbles
    42 Reviews
    3 BedroomsSleeps 6Quick View
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    Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West. Hidden behind the most photographed "prohibition fence" in Key West, this three bedroom, two bathroom home includes a large sunny pool and patio as well as off street parking (1...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Welcome to a truly magnificent Key West conch home. Ellen's Casa resides on the lovely Pearl St in midtown Key West just a couple blocks away from parks, marinas and only a 5 minute drive to Duval St. The high class neighborhood is home to many local residents and is very quiet, no matter the time...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    47 Reviews
    1 BedroomSleeps 2Quick View
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    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    StudioSleeps 12Quick View
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    Classic romantic 1800’s Key West architecture has inspired a superbly executed renovation of this extraordinary historic Victorian estate. Displaying a perfected cosmopolitan flair, the owner / designer has artfully intertwined a look-back into architectural history with a sophisticated...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bathrooms, Sleeps 12
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    4.5 of 5 bubbles
    9 Reviews
    3 BedroomsSleeps 8Quick View
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    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50", 42", and 27" flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 of 5 bubbles
    2 Reviews
    12 BedroomsSleeps 30Quick View
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    • Private Outdoor Pool (Unheated)
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    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This rental offers a great option for multi-family vacationing by providing three 4-bedroom homes side-by-side. This gives you 3 kitchens, 3 pools, 3 deep water docks, 3 gas grills, parking for 8 vehicles and 6 kayaks! These properties are non-smoking and...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 12 Bedrooms, 8 Bathrooms, Sleeps 30
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    4 of 5 bubbles
    6 Reviews
    StudioSleeps 10Quick View
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    • Hot Tub
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    Pet friendly
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    This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites. Opposites attract...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bathrooms, Sleeps 10
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    • Private Outdoor Pool (Unheated)
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    About this property
    TOWNHOUSE TOTALLY RENOVATED AND FURNISHED TERRACES OFF EVERY ROOM (4) BAYFRONT WITH DOCK, POOL TIKI HUT , CARPORT FOR TWO CARS,CENTRAL AIR,WASHER AND DRYER,WIFI,DISHWASHER,MICROWAVE AND CABLE TV FOR 3 TVS GAS BARBEQUE IN UNIT,STORAGE SHED,AND BEACH CHAIRS CLOSE TO RESTAURANTS AND SHOPPING...
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    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    9 Reviews
    2 BedroomsSleeps 5Quick View
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    7 day minimum please Key West Vacation Rental This fully furnished newly updated getaway! It is so close to all the Beach, our pool and the local Key West bars & restaurants and museums just take a short stroll or jump on a bike and a way you go... Our gated pool is climate controlled with plenty...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    • Balcony
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    • Ocean Views
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    About this property
    Experience total seclusion in this ten-unit oceanfront complex called Port of Call, nestled along Millionaire's Row in Plantation Key, Islamorada on the Atlantic Ocean, Mile Marker 88. Outdoor facilities include a heated pool; chickee hut with common area barbecue grills, Volleyball courts on a...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    28 DAY MINIMUM RENTAL .... NO PETS ACCEPTED Break away from it all at Escape on Fleming. This comfortable and fresh two bedroom one bathroom apartment is located in the heart of Old Town. Conveniently located near charming Old Town restaurants such as Azur and Cafe Sole, yet off the beaten path,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Waterfront Home in the heart of the Florida Keyes. Come relax and enjoy the beautiful waters of Sombrero and Bahia Honda Beaches. Both nearby. There is plenty of room and comfort in our 4 bedroom, 3 bath home. Two King Master Suites with attached baths. Satellite Flat Screen TV's in each...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Canal front, two bedroom, two bath home with relaxing tropical decor and colors. Shaded canal side area with patio furniture for dining or relaxing. For the fisherman a 35' concrete dock/seawall with dock posts, cleats, ladder and fish cleaning table. Florida style living room has glass sliders...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    This property is quite the hidden gem! Located on the second story of one of the most famous streets in the world, you will find Duval Dreamin'. The home over looks Duval Street and features TWO living areas, TWO bedrooms and TWO bathrooms. This is the perfect pad for couples, friends or family...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    2 Reviews
    2 BedroomsSleeps 6Quick View
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    About this property
    Take a trip to the Fabulous Florida Keys and stay at Tarpon Cove at OCEAN POINTE RESORT CONDOS, a private 65 acre tropical resort. Our totally renovated 2 bedroom/ 2 bath beautifully furnished apartment. Sleeps 6 and is ready for you and your family. Tropical landscaping, sandy oceanfront...
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    Tavernier, Key Largo 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Our Key West condominium, Casa Tropico is a 2 bedroom, 1 bath ground floor condominium. The master bedroom has a queen size bed, the second bedroom has 2 twins. A double set of French doors in the living room open onto the rear deck. The deck overlooks a quiet walking lane. Outfitted with table,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
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    3 BedroomsSleeps 8Quick View
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    • Private Outdoor Pool (Heated)
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    This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it’s own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 of 5 bubbles
    13 Reviews
    3 BedroomsSleeps 6Quick View
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    About this property
    “Southard Comfort” is true Island living in downtown Historic Old Town Key West. Two story, 3 bedroom, 2.5 bath plus outdoor shower Nancy & Carl welcome you to their Key West vacation home! This established rental is a dazzling property, and we are committed to continuing its reputation of...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    About this property
    For your next Florida Keys vacation, reserve a stay at this waterfront home located on a canal with easy access to either the Atlantic or the Gulf. This home has everything you need to enjoy a relaxing vacation with resort amenities at your backdoor. Featuring 2 bedrooms, 1 bathroom. The master...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    About this property
    CANAL FRONT Charming Private Pool Duplex! 2 bedroom, 2 bathroom with loft. Sleeps 6 with optional 7.This half duplex home has everything you need for the perfect getaway included heat optional private pool. This unique home has a fully equipped kitchen with bar seating, open floor plan,...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    5 of 5 bubbles
    2 Reviews
    3 BedroomsSleeps 8Quick View
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    Pet friendly
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it’s own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    This impressive home is located in Islamorada on a private lagoon with quick direct access to the Florida Bay. Featuring 5 bedrooms and 5 bathrooms, this private residence offers plenty of balconies for water viewing, expansive cathedral ceilings, top of the line appliances and ceiling fans...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    4.5 of 5 bubbles
    7 Reviews
    StudioSleeps 8Quick View
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    About this property
    Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This tropically...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bathrooms, Sleeps 8
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    5 of 5 bubbles
    1 Review
    3 BedroomsSleeps 5Quick View
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    • Shared Outdoor Pool (Unheated)
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    Smoking allowed
    About this property
    Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    5 of 5 bubbles
    9 Reviews
    2 BedroomsSleeps 6Quick View
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    • Patio
    • Washer
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    • Waterfront
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Royal Palm House. Home is located at Mile Marker 54.5 in Coco Plum Beach Subdivision in the heart of the Florida Keys. This custom built contemporary home features 1,515 square foot of central air condition and heated living space. Massive Great Room has vaulted ceilings, clay tile...
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    Marathon, Florida Keys FL
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Washer
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    • Balcony
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    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is in a very quiet section of a quiet island . It is surrounded by palm trees. There is a large screened deck which catches the breeze. At the end of the canal (approximately a block ) you will be in a large open area between Big Pine and Little Torch ; from there you can easily travel...
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    Location Information
    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 of 5 bubbles
    4 Reviews
    3 BedroomsSleeps 6Quick View
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    • DVD Player
    • Air Conditioning
    • Ocean Views
    • Waterfront
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    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located just 90 miles south of Miami and 45 miles from...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    16 Reviews
    3 BedroomsSleeps 8Quick View
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    • Internet Access
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Washer
    • Ocean Views
    • Waterfront
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the relaxing, laid back lifestyle of Key Largo. For those who love diving, fishing, snorkling, boating, or just simply letting the world go by while relaxing oceanside. Feel free to contact me whenever you are ready - we are waiting for your call! Beds: 3 King Beds, 1 Sofa Bed
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Patio
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    • Internet Access
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    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Slip into the beach lifestyle and leave the daily grind behind when you book your stay at this oceanfront Layton cottage. With a dock, expansive deck, and a stunning beach location, you may never want to leave. With historic roots as the home to the 1900's author, Zane Grey, and easy access to a...
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    Location Information
    Long Key, Florida Keys 33001
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 of 5 bubbles
    1 Review
    1 BedroomSleeps 2Quick View
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    • Private Garden
    • Air Conditioning
    • Shared Garden
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    • Parking
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <BR> KEY WEST VACATION CONDO RENTAL DESCRIPTION<BR><BR> Our beautiful deluxe one bedroom condo in Key West Florida on<BR>Southard Street is just blocks from the ocean and Duval street.<BR>Located in historic old town, the condo is enclosed in a beautiful<BR>garden on the ground floor. It is...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 BedroomsSleeps 6Quick View
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    • Private Outdoor Pool (Heated)
    • Balcony
    • Washer
    • Sauna
    • Internet Access
    • Grill
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautifully renovated high end luxurious monthly rental at 1800 Atlantic. The moment you walk in you will appreciate the attention to detail. Enjoy the lovely views of the complex and Atlantic ocean from the private balcony. The master bedroom suite has a brand new king size bed. The...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    1 Review
    3 BedroomsSleeps 8Quick View
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    • Private Outdoor Pool (Heated)
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    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 BedroomsSleeps 3Quick View
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    • Ocean Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Directly on your private oceanfront beach. Ocean views from every room of your two bedroom one bath Keys style duplex villa.You will experience the true 'old Keys' charm of bird watching on the wraparound deck to fishing on the beach...or perhaps just relaxing on the sand.With over a half acre of...
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    Matecumbe Key, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    2 BedroomsSleeps 6Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful two bedroom, two bath home in Marathon has a fantastic Gulf view and quick, easy access to open water! Very spacious, concrete dock, sundeck on top of home makes for spectacular sunrise and sunset scenes. Master bedroom has king bed with sitting area and full bath. Second bedroom has...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 of 5 bubbles
    2 Reviews
    2 BedroomsSleeps 4Quick View
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    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Parking
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 7 Days "Moon Bay #A410" is a 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and appliances. New linens...
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    Location Information
    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    StudioSleeps 2Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our efficiencies/Studio apartments are located 50 yards from the Ocean. All units are fully furnished with equipped Kitchens,lines, and baths. Each efficiency has a small outdoor space sharing a common front yard with tropical foliage, individual gas-BBQ grills, picnic tables and umbrella's for...
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    Location Information
    Grassy Key, Marathon 33050
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    5 of 5 bubbles
    2 Reviews
    4 BedroomsSleeps 8Quick View
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    • DVD Player
    • Waterfront
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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