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Holiday Rentals in Florida Keys, FL

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    Travellers to Florida Keys are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    Islamorada
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Marathon
    3 Bedrooms, Sleeps 6 | Quick View
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    2.5 of 5 stars (2) Poor
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 38
    5 of 5 stars (36) Excellent
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Oceanfront splendor on the Atlantic ocean. Has a 350' pier that can accomodate most any size boat. Just relax by the pool on those hot days or take a dip in the ocean. The pool is heated for the winter months. The house is extremely private. There is a wooden fence around the house and... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    Key Largo
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    WWW.KEYLARGODREAMS.COM Our delightful home comfortably sleeps 10 and features 2 baths, 2 showers, 1 tub, and 4 lovely bedrooms. Bedroom 1 has a queen-size bed. Bedroom 2 offers 2 full beds. Bedroom 3 includes 2 twin beds. And, bedroom 4 is perfect for the kids with 2 sets of bunk beds. Featuring... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 9
    5 of 5 stars (1) Excellent
    Tavernier
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Sunset view,tennis courts, heated pool, recently remodeled,fish from the dock,boat slip right in front of unit. quiet gated community, monthly $3850.00 in season, $2850.00 out of season Weekly $1450 per week in season, out of season $1250 per week This 2 bedroom townhouse, with built in bar,... View all property information
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    Tavernier, Key Largo
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable reopening price and enjoy! If we find that the house has been left excessively dirty,... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Terrace
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    About this property
    Newly remodeled split level townhouse In Luxurious Mariner's Club Private Resort. 3 bedroom/3 bath with sleeping accommodations for up to 7. Balconies with seating on 2nd and 3rd floors facing the marina and picnic areas. Beautiful sunrise views. Great Amenities on-site including Fitness Center,... View all property information
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    Key Largo, Florida Keys 33037
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Completely renovated keys cottage. Classic and charming design with modern amenities. This is a concrete home on the ground level, not a trailer or mobile home. Master suite with bath on ground floor. Two bedrooms upstairs with balcony overlooking Buttonwood Sound. Lots of room for the whole... View all property information
    Location Information
    Key Largo, Florida Keys 33037
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    1 / 50
    5 of 5 stars (13) Excellent
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    $1,500 (Standard Rate for 2016) - additional rates apply to holidays and Lobster Weeks.ASK ABOUT REDUCED FALL RATES! (September 2016- December 17, 2016) Reduced rates do not apply to holiday weeks. PRIVATE-ON-SITE POOL, 45 FT DOCK, CABANA CLUB, GROUND LEVEL, CARPORT, W/D, BAIT FREEZER,OUTSIDE... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    1 / 30
    Marathon
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** Walk to Sunset Park - Located down the block! "Island Bay" Tropical large five-bedroom, four bathroom home on a deep water canal with boat dockage in Key Colony Beach. Private upper level king master bedroom suite... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 19
    5 of 5 stars (6) Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    <b> Minimum Rental: 7 Nights </b> You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who treasure... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 11
    5 of 5 stars (2) Excellent
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Beautiful Keys luxurious home at canal five house from Atlantic Ocean . It offers 50ft dock along with powers . Through boat about 4/5 minutes to Vaca Cut & about 7/9minutes distance from 7 miles Bridge . About 20 minutes distance from the Sombrero Reef . Through land about 10 minutes short... View all property information
    Location Information
    Marathon, Florida Keys 33050
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
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    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    5 of 5 stars (1) Excellent
    Key Largo
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Relax laying on the hammocks and enjoy the ocean breeze from this 4 bedroom 2 bath newly remodeled vacation home. Located on the same street as the Private Community Boat Ramp. You will be able to launch your boat and be on the ocean side or cross via Adams Cut to the bayside in minutes. Everything... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 22
    3.5 of 5 stars (10) Average
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Cute and CozyMobile Home located in gated community of Venture Out MM 23 in the Florida Keys. 2 bedrooms and 1 bathroom on a dry lot along the fence. Fully equipped kitchen, newer refrigerator , self cleaning oven, free internet, Cable, 50 inch flat screen TV in living room 4 brand new A/C's 2... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 25
    4.5 of 5 stars (6) Very good
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    <b> Minimum Rental: 7 Nights (Saturday to Saturday)</b> BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 15
    5 of 5 stars (2) Excellent
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    <b> Minimum Rental: 7 Nights SATURDAY to SATURDAY</b> Calling all fishermen and divers... Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. World famous dive sites are minutes away and phenomenal fishing is... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 17
    4 of 5 stars (1) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    For those of you who want to stay as close to Key West as possible without paying those outrageous Key West prices, stay with us between mile marker 10 and 11 in this waterfront condominium. This small, yet efficient penthouse condominium, 672 sq. ft., stands alone as a roof unit on building 3 of... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 16
    Grassy Key
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    About this property
    Imagine gazing across a large, sparkling swimming pool to see a natural in-ground aquarium..... Big enough to swim in and filled with tropical fish. The dock accommodates large boats drawing 5' + The home sits on almost 3 acres of landscaped property The house is large and can handle big groups... View all property information
    Location Information
    Grassy Key, Marathon 33050
    Cudjoe Key
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Waterfront 120' Dock - Extensive Tropical Gardens Abound - Privacy - New Stainless Steel Appliances - 3 Bedrooms - Home Newly Remodeled and Redecorated - 300 sq' Elevated Deck - Pets Welcome w/ Fenced Backyard - New Bathroom Featuring Large 3 Head Shower - New King Size Sleep Number Bed - Fully... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    Marathon
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • x
    About this property
    Ocean Front - Villa Bali inspired Florida Keys beauty on Privately owned Walker's Island. This is a spacious 5 bedroom, 5.5 bath home with luxury in every detail and design. Features include cathedral ceilings, marble, stainless steel and and mahogany finishes, and fireplaces in the living room... View all property information
    Location Information
    Marathon, Florida Keys 33050
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
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    About this property
    Enjoy the Florida Keys without breaking the bank! Come and stay in our little piece of heaven and take advantage of all the Keys has to offer. Located about an hour south of Miami, this quaint home offers a king bed in the large master bedroom and a comfortable queen bed in the second bedroom and a... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Wonderful two story townhome in a private, gated community with all amenities you'd expect while on vacation. Inside: Newly renovated and remodeled unit. Fully equipped kitchen and stainless appliances, large storage cabinets with pull outs. Granite counters etc. Living room area with 60 inch... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 27
    5 of 5 stars (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights***<BR><BR>MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS<BR><BR>Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    4.5 of 5 stars (5) Very good
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Porch
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    About this property
    We offer a 34 Ft 5th Wheel with all utilities hooked up minutes away from major stores and attractions.You need not bring anything other than your cloths and snorkeling equipment.We have everything the most demanding outdoor adventurer would expect.As our guest you have access too our pool located... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 24
    3.5 of 5 stars (3) Average
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Outdoor Dining Area
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    • ?
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    • x
    About this property
    Half duplex located in prestigious Key Colony Beach. Tropical decor throughout. Located on a 100ft. wide canal with quick access to ocean. There is a concrete dock for your boat, and a great patio in the back. You are within walking distance to the "Cabana Club" , a private beach club with a... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33050
    1 / 28
    5 of 5 stars (5) Excellent
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick 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... View all property information
    Location Information
    Marathon, Florida Keys 33417
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    Duck Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Duplex in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait and tackle shop, bank, jewelry store, and much more. Two marinas that you can use, rental of jet skis, kayak boat, sailing boats, snorkeling and fishing trips. You have access to... View all property information
    Location Information
    Duck Key, Florida Keys
    1 / 13
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** Enjoy spectacular sunsets and beautiful waterfront at **Caribbean Sunset**. This spacious three bedroom, three bathroom home has a well appointed kitchen, three king bedrooms (one converts to two twins) and a beautiful... View all property information
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    Marathon, Florida Keys 33050
    1 / 9
    4 of 5 stars (1) Very good
    Key Largo
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    2 bedroom, 2.5 baths, sleeps 6, Townhouse<BR><BR>Beautiful, recently remodeled, 2 bedroom, 2½ bath townhouse in gated, bayside community. Fully equipped with everything you need to enjoy a great vacation in this tropical island paradise. Heated swimming pool, toddler pool, marina, boat ramp,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 14
    4.5 of 5 stars (3) Very good
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautifully refurbished 4th floor condo has great marina and ocean views from the living room, master bedroom & balcony! Gorgeous wood floors throughout and new furnishings lend an elegant atmosphere with lots of comfort in mind. Master bedroom has a king-sized bed, while guest bedroom has 2... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    Big Pine Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Welcome to the Lazy Manatee. We are located on Big Pine Key,Fl. Our passion is to provide a place to relax while enjoying all the wonders of the Florida Keys. Big Pine is home to the famous Key Deer, an endangered species that can be seen throughout this area. The Lazy Manatee is a spacious 2... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 32
    5 of 5 stars (1) Excellent
    Marathon
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Lush Tropical Waterfront Homes with Incredible View, Pool, Tiki Hut and 100' of Deep Water Dockage - Full Duplex (two homes, one property, one price). Spectacular view of the Gulf of Mexico and incredible sunsets. With this full duplex home you get two large side-by-side 2 bedroom, 2 bath homes.... View all property information
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    Marathon, Florida Keys 33050
    1 / 30
    5 of 5 stars (36) Excellent
    Key Largo
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
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    • x
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    Bay front Vacation Condo in Key Largo, Florida. <BR><BR>We book early so don't wait, beat the rest to one of the best and most reasonable, clean, and well appointed condos in beautiful Key Largo, Florida.<BR><BR>We now Accept PayPal, at a small fee.<BR><BR>Beautiful sunsets, water view from our... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 66
    5 of 5 stars (20) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    Don't hesitate to call us! Many folks prefer to speak with a real live person. We're here to help :) 517-420-4212 (call or text- anytime!) Read 90+ guest reviews at www.homeaway.com/177656. Welcome to the beautiful Florida Keys! We're Greg and Stevie (Stephanie) Bovee from Carbondale, CO. We... View all property information
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    Key Largo, Florida Keys 33037
    1 / 15
    4 of 5 stars (9) Very good
    Duck Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • x
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    LATE FALL SPECIAL DEALS; RATES AS LOW AS $125 PER NIGHT. LATE FALL IS GREAT IN THE KEYS!, Situated in the grounds of Hawkscay hotel and resort, on the beautiful upscale island of duck key, this lovely villa boasts a quality recently refurbished interior. Outside there is a waterfront private... View all property information
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    Duck Key, Florida Keys 33050
    1 / 19
    5 of 5 stars (1) Excellent
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This one-of-a-kind Fantasy Resort Villa vacation rental perfectly blends two charming historic cottages right into a little bit of island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard of this extraordinary property just off Upper Duval St. in... View all property information
    Location Information
    Key West, Florida Keys 33040
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    Fantastic 2 bedroom, 2 bath condo resort. Enjoy the breathtaking view of the Atlantic Ocean from the patio just steps from the white sandy beach. Make sure you head out to the pier each evening at sunset to see picture postcard views. <BR><BR>This condo is fully equipped with two large bedrooms... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    1 / 9
    3.5 of 5 stars (3) Average
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    MINI VACATIONS 3 DAYS 2 NIGHTS $250 April 1 - May 15, 2015 This Key Largo property is a paradise in a gated private community. This comfortable park model trailer includes cable TV, full kitchen, bathroom, Queen size bed in master bedroom and much more. Outside terrace with BBQ grill and... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 29
    5 of 5 stars (38) Excellent
    Key West
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Private Outdoor...
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    • x
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    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer.... View all property information
    Location Information
    Key West, Florida Keys 33040
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    Located at the end of the marina with breath taking views of sparkling waters and the setting sun, Coquina is a cottage with a lot of history that whispers from the past with old Florida comfort and charm. Spacious, tropical and beautifully decorated, the cottage is made from Dade County Pine with... View all property information
    Location Information
    Marathon, Florida Keys 33050
    1 / 25
    5 of 5 stars (6) Excellent
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Outdoor Dining Area
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    • x
    • x
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    Relax in this peaceful, open-water, bird and wildlife sanctuary with private views of the State Park. From your private deck only 9 feet from water's edge, you can watch fish swim and birds fly, or if you prefer, you may simply sit and enjoy the ebb and flow of the tide. In these environmentally... View all property information
    Location Information
    Marathon, Florida Keys 33001
    Key Largo
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Central Heating
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    • x
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    • x
    About this property
    Newly remodeled split level townhouse in luxurious Mariner's Club Private Resort. 3 bedroom, 3 1/2 bath with sleeping accommodations for up to 8 guests. Unit is a 2 bedroom/2 1/2 bath + 1 bedroom/1 bath efficiency with kitchenette. Balconies with seating on 1st and 2nd floors. Great amenities... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 42
    4.5 of 5 stars (2) Very good
    Tavernier
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    • Porch
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    • x
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    About this property
    This is a beautiful home, you will enjoy every minute of your stay here! There aren't many homes built like this in the Keys. The room for rent is the guest room (the other room is occupied), with 14 foot vaulted ceilings, a comfy, queen sized bed and a ladder leading to a crawl space above (see... View all property information
    Location Information
    Tavernier, Key Largo 33070
    Key Largo
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    If you are looking for a spacious, beautifully furnished & decorated house located in Key Largo to have fun with your family and experience beautiful sunrises and sunsets, wildlife, and marine life, This is a fabulous place next to the channel. You will love the peacefulness and the nature.The... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 31
    5 of 5 stars (23) Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen television, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful... View all property information
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    Islamorada, Florida Keys 33070
    1 / 17
    5 of 5 stars (19) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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... View all property information
    Location Information
    Key Largo, Florida Keys 33037