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Holiday Rentals in Florida Keys

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    Travellers to Florida Keys are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    3 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    1 Bedroom, Sleeps 2Quick View
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    6 Bedrooms, Sleeps 16Quick View
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    2 Bedroom 2 bathroom high ceilings spacious unit in Truman Annex. Bright and Airy floor plan with cathedral ceilings, balcony. Highly desirable and rare 2 bedroom, 2 bath unit. One assigned parking space, large community pool and short distance to Fort Taylor Beach. Short walk to Duval Street,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    14 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    About this property
    This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 5Quick View
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    Minimum Rental: 28 Days "West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    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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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. La Brisa is a two bedroom two bath condo on the third floor. The master bedroom has a king size bed with a walk in closet, a desk...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Satellite TV
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    • Private Outdoor Pool (Unheated)
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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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    9 Reviews
    3 Bedrooms, Sleeps 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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    2 Bedrooms, Sleeps 4Quick View
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    MINIMUM RENTAL REQUIREMENTS due to licensing restrictions; rates go down the longer you stay; deals and specials offered. Quiet end unit located in the Truman Annex. Just steps away from Fort Zachary State park/beach; two blocks from Duval Street and one block from The Green Parrot. Walking...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    25 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • Private Outdoor Pool (Heated)
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    LAVENDER JUNGLE - Beautiful 2 bedroom 1 bath downstairs Shipyard condo for rent Key West located in Truman Annex, this home has a renovated kitchen and upgraded bathroom. For those who don't want to climb stairs, this property is on the first floor and has a large brick patio and grill. Master...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    About this property
    This adorable, well-lit 3 bedroom, 2 bath duplex is on a canal, features a fishing table and is perfect for family reunions, weddings or vacation rentals of any kind. The Florida Keys are internationally known for their natural beauty, spectacular weather, world class fishing, snorkeling and...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, Sleeps 4Quick View
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    This property has it all. The seawall is 35’ with cleats, posts and fish cleaning table and a propane grill. Step up to a covered deck which has patio furniture to enjoy the canal view and perhaps happy hour and dinner. Enter Florida room through glass sliders into living room which has a flat...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
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    About this property
    Minimum Rental: 28 Days "Casa Dorado" is an exceptional privately owned single family home located directly on Florida Bay on Lower Matecumbe Key in Islamorada. The house is named after the owners' favorite species of fish, the Dolphinfish, also known as Dorado in Spanish speaking coastal...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Waterfront
    • Balcony
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Cayo, a Magnificent Florida Keys Home With a Bay View, Located in Islamorada at Mile Marker 88.5 in the Exclusive Gated Community of Futura Yacht Club. Casa Cayo Has Been Completely Updated Throughout and Includes Many Luxury Features to Make Your Stay Relaxing and Enjoyable. This...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 10Quick View
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    About this property
    Beautiful home with 3 bedrooms and 2 bathrooms,everything renovated,kitchen remodeled with stainless steels appliances ,the house have comforted beds for 10 people's ,backyard area with BBQ ,private parking inside the house for 6 cars,private ramp for boat and jetski inside the house,beautiful...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    • Patio
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    • Ocean Views
    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    This deluxe three bedroom waterfront condo is on MM 99.5 in Key Largo. It is a 3-story unit with beautiful views of the Atlantic Ocean. The unit has 3 spacious bedrooms, each with a queen size bed. You also have the convenience of having a full size washer and dryer in the unit. Other amenities...
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    Key Largo, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Satellite TV
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    About this property
    While relaxing in the free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Upon entering the 3200+ square foot home, the spacious nature of the home is evident providing ample room for large groups. Around the back of the home, the large deck with...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 18
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    2 Bedrooms, Sleeps 4Quick View
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    Affordable vacation home beautifully decorated in peaceful pastel colors. This home has many nice features including being bright, spacious and tropically decorated. The living room area has a Flat screenTV with DVD & VCR, queen size sleeper sofa, glass top table and comfy chairs. Master bedroom...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    11 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Key Colony Beach house (duplex) description SPECIAL rate of $1100 for 4 guests (may have 6) $10 per extra person per day, 6 max total) Valid for Spring ( check rates) Summer is $1200 per week, excluding lobster weeks which are $1700. 2018 Winter rates are $5200 per month for Jan Feb Mar, only...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    19 Reviews
    2 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
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    Pet friendly
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    About this property
    Located one hour from Miami, Florida... the Kawama Yacht Club is your escape route to the Florida Keys. Situated at mile marker 100 on the Atlantic Ocean, this gated community offers all you need for a relaxing vacation or getaway. Enjoy the panoramic view this 5th story unit has to offer of the...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10Quick View
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    • Ocean Views
    • Air Conditioning
    • Housekeeping Included
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    • Waterfront
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    110 Feet of Direct Gulf Front Spacious Home with Spectacular Sunsets. Part of the experience includes Kayaking (included 2 doubles with life vests) right from our steps. Relax in the Sun, use the 10 foot Jacuzzi Spa, and wait for the extraordinary sunsets that change by the minute. Beauty and...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Review
    4 Bedrooms, Sleeps 10Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    About this property
    Minimum Rental: 28 Days "Conch Bar South" is a magnificent home is located at the mouth of a wide canal in Plantation Key and offers phenomenal open water views. The furnishings are new and provide a comfortable and extremely inviting living environment. This 4 bedroom 3 bath single family home...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Reviews
    1 Bedroom, Sleeps 4Quick View
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    About this property
    Looking for the perfect Key West get away or corporate retreat? Look no further, here is your opportunity. This little gem is located one block from the world famous Duval Street. This stunning second floor, one bedroom one bath condominium is filled with quality, style and class throughout. The...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • Ocean Views
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    This is a beautiful 4 bedroom, 3.5 bath single family home. The home is located in the very desirable, Sombrero Beach area. There is a private pool, deep water dockage and washer/dryer. This is a spectacular home offers 2 levels of living space with beach views from the dining room, living room and...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Internet Access
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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 6
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    3 Bedrooms, Sleeps 8Quick View
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    About this property
    This is a waterfront manufactured home that has been upgraded. You can rent the home with or without the boat. You can relax in the waterfront Tiki hut or float in the pool. The house is very convenient to either the ocean or bay side of the island. House comes complete with cable tv in every...
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    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Review
    3 Bedrooms, Sleeps 8Quick View
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    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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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex consisting of 70 units. Enjoy wonderful Bay views and sunsets from our two bedroom / two bath condominium unit that sleeps up to 6 people. Stay in...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    15 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    About this property
    NEWS BULLETIN. JUST HAD A CANCELLATION FOR THE WEEK OF MAY 20 TO 27 AND JUNE 17 TO 24 IN MY OTHER CONDO IN KEY WEST THAT WILL ACCOMMODATE UP TO 4 PEOPLE SO I WILL DO RIGHT BY YOU WITH THE RATE. Now onto my cottage. . Envision yourself unwinding and getting into the casual clothes we wear in Key...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Brand new, state-of-the-art home in Coco Plum. Concrete construction, metal roof, three floors, four bedrooms, four baths, 3,356 SF under air, plus another 1,500 SF of porches. Fabulous exterior living areas. Huge kitchen with Hansen & Bringle custom cabinets, GE Monogram Appliances! Super-high...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Review
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    Q: What's better than vacationing in the Florida Keys? A: Vacationing in a charmingly cute canal-front home in the Florida Keys! And this home takes the cake for cute! Located at mile marker 101 on the bay-side in Key Largo, this home is equipped to make your month (or longer!) in the Keys one to...
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    Key Largo, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    30 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    Havana Lane hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery, this classic conch cottage embodies the essence of rustic charm while offering modern amenities and style. Centrally located...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, Sleeps 6Quick View
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    Full Kitchen Weeks are Friday to Friday and Saturday to Saturday only Coral Lagoon Resort & Marina is a waterfront Marathon, Florida resort that offers extraordinary luxury. Our intimate hotel in Marathon features 25 beautiful Key West Conch-style villas and cottages dotted through six acres of...
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    Marathon, Florida Keys 33050
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    27 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this Key West vacation rental offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    Breezy Bungalow - Weekly Rental When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside breezes to flow openly into Breezy Bungalow. Two levels of...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    3 Bedrooms, Sleeps 6Quick View
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    Smoking allowed
    About this property
    30 night MINIMUM STAY Picture yourself on a tropical island, half-asleep in a poolside lounge chair. Feel your body succumb to the tropical breeze as it gently cascades over you, draining your stresses away! It is not a dream! It is life in Marathon, heart of the Florida Keys! In a recent review...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Waterfront
    • Air Conditioning
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 2 story, 2 bedroom, 2 bathroom townhouse that comfortably sleeps 6 in a 24 acre Resort / Condo complex. Included in the price are Taxes, Cleaning, WiFi, a Golf Cart, Kayaks, Paddle Boards, Bikes, Fishing Gear, Snorkeling Gear, Tennis Equipment, Towels, Linens, Kitchen utensils,...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Terrace
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Satellite TV
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Infinite ocean views from the large balcony at this modern and luxurious oceanfront condo at mile marker 87. BOAT SLIP INCLUDED which can accommodate up to a 30' boat. SLEEPING ARRANGEMENTS (Sleeps 4) Master Bedroom: - King Size...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    • Air Conditioning
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Full Kitchen Weeks are Saturday to Saturday only Ocean Pointe Suites in Key Largo is located on a 60-acre ocean front sanctuary, surrounded by lush tropical landscape and the iconic blue waters of the Florida Keys. From sunrise to sunset you can enjoy the many activities Ocean Pointe has to offer...
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    Location Information
    Tavernier, Key Largo 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Secure Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious and clean 3 bedroom 2 front canal front home. Bring you water toys. Access to open ocean from house. Large deck with spectacular sunset views. Large heated pool, private yard. Walk or bike to Beautiful Sombrero beach. 3 bedroom, 2 bath very clean and neat. Great location, beautiful...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    This beautiful custom home located in Jolly Rodger subdivision on Little Torch Key has the best of everything. Just furnished in 2012 with the finest tropical decor, flat screen TV's, wireless internet and top of the line gourmet kitchen. The large living area is spacious and cheery with tall...
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    Location Information
    Little Torch Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Reviews
    3 Bedrooms, Sleeps 8Quick View
    other travellers have booked this property
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    • Hot Tub
    • Satellite TV
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, Location, Location! Ocean View, Lagoon Beach Front. This 83' Luxury Houseboat is located at 6000 Peninsular Ave. Key West, FL 33040, slip 25. The property is furnished and includes: linens, towels, 3 bedrooms, 3 beds, 2 full baths, 1 Large pull-out couch, all kitchen appliances,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Waterfront
    • Hot Tub
    • Ocean Views
    • DVD Player
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    • Children's Pool
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfectly positioned on Sunset Key, ‘the islands island,’ the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the ‘main island’ of Key West. A splendid view gazing toward Mallory Dock and the famous sunset celebration, this one-of-a-kind waterfront property offers a...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 10Quick View
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    • Private Garden
    • Wi-Fi
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Live your tropical dream at this palatial oceanfront estate. Located near mile marker 89, on Islamorada's Millionaires' Row, this 4 bedroom / 6 bath home comes with just about every convenience you can imagine, as well as some you probably haven't even considered. Enjoy a swim in the pool that...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    • DVD Player
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for your next friends or family getaway to the Florida Keys, this Key Largo condo in the Ocean Point Suites offers room for up to seven, plus access to community amenities like a private dock and boat marina, tennis courts, a private beachfront area, a hot tub, and a large pool with a...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 10Quick View
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    • Internet Access
    • Satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Terrace
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 6Quick View
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    • Washer
    • Balcony
    • Private Outdoor Pool (Heated)
    • Grill
    • Sauna
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Monthy rental on the Island side of the property. Queen bed in the master bedroom and a double in the guest. Updated kitchen. For your convenience there is a desk area set up in the living room for those that have to work whilst away from home. Beautiful updated kitchen and a washer/dryer....
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Washer
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Grill
    • Internet Access
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Balmy weather, sunshine and a little magic await you in the Florida Keys… Look no further than this exquisite Islamorada vacation rental home as your own personal oasis during your upcoming tropical getaway! Nestled in the exclusive oceanfront gated community of Angler’s Reef in Islamorada on...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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