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Holiday Homes in Cudjoe Key

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    Travellers to Cudjoe Key are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    All 30 Rentals in Cudjoe Key
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort1 / 11
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 2 Kayaks and padl board1 / 12
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the breathtaking open water views from the multi-level porches of Waterside Bay! This 3 story custom home has 3 bedroom and 3 baths and has upscale yet comfortable living. Complete with a Gourmet Kitchen of stainless steel appliances and granite counters making entertaining a breeze....
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes, is located right in the center of the Lower Keys. Key West is only 16 miles in one direction and Marathon 25 miles in the other. This 1200...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • DVD Player
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy Paradise in the comfortable island style of Catch of the Day! This 2 bedroom 2 bath canal front home on Cudjoe offers the casual lifestyle of the Lower Keys. It features all amenities including new furnishings, a well appointed kitchen and fresh linens. A large under-house storage area...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Concrete home with canal front view. 80 foot concrete dock with easy access to the Gulf and Ocean. Lots of parking on the oversized lot . 3 screened in porches for outdoor entertaining. The home is well stocked with everything you’ll need to enjoy your stay. This is a 28 day minimum rental....
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Family Retreat ocean front home with private pool1 / 25
    (15)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Grill
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    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2018
    Nice large house with plenty of space .Not much Beach or Access to fishing without a Boat as the water is very shallow in this whole area. Easy drive to whatever you are wanting.
    Reviewed 21 December 2017
    This is the PERFECT Family retreat! Each year, my husband and I take our 5 grown kids and their significant others to the Keys for a family vacation. We've tried multiple...
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    About this property
    Oceanfront 6 bed/4 bath home with panoramic ocean view on Cudjoe Key. Sleeps 12+. Beach, Hot Tub, Floating Dock, Heated Pool, Kayaks and 540 square foot screened in porch overlooking the Atlantic ocean. This house has been very popular with large groups. New memory foam mattresses in 2018....
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Terrace
    • Private Garden
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Deep water canal, bring your boat or rent one, sunset vies from balcony, lagoon view and peak of the Atlantic Ocean. Brand new bed linens with every stay, everything else very clean, security system, large capacity fridge to storage all your catch, fishing boat available for rent, off street...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Hot Tub
    • Terrace
    • Grill
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom 2 Bath Sleeps 6 Tropically Decorated Stilt Home Lovely Covered Porch with Water View You won't be disappointed in the beautiful decorated 2 Bedroom/2 Bath stilt home with a canal view. Relax on the covered deck with privacy palms. Lovely tropical decor with a nice size living room and...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fandango1 / 24
    (12)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Waterfront
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2017
    Our family and friends had an amazing week at Fandango. Everything from the location, to the amenities was perfect. The house had all you needed to create unforgettable family...
    Reviewed 8 December 2016
    My daughter-in-law leased Fandango House for 3 days to celebrate the birthdays of my two children and myself. Fandango is a beautifully kept vacation rental that has all the...
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    About this property
    Designed as the ultimate vacation rental. Five Bedroom/Three Bath Oceanview Home with Heated Pool and Hot Tub. Panoramic Ocean Views. Sleeps 10+. Located on Cudjoe Key. Includes private boat dock, private beach, kayaks, and bikes. Weber BBQ grill, Lot's of lounge chairs and two hammocks....
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Tropical Paradise Oceanfront Home with Pool1 / 24
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2017
    Our family of four loved everything about this property - the location, the kayaks and bikes that are provided, Cudjoe Bay (which is just steps from the deck), the view! So...
    Reviewed 19 July 2016
    I had originally reserved a larger house a few streets down from this one. That was when there was going to be a much larger group. However, due to the fact that some friends...
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    About this property
    Paradise found, this house has it all, beach, dipping pool, screened in porch, kayaks, bikes, floating dock and amazing views. This has been a popular honeymoon and anniversary celebration home for over 15 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Blue Adventure Waterfront at Venture Out1 / 29
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Waterfront
    • Hot Tub
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    • Ocean Views
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable and charming, this newer stilt home has everything you could want for a vacation for just the two of you, a few friends, or the whole family! Fantastic waterfront open canal views. Located on a 60' wide canal, you can bring your powerboat, jet ski, kayak, or what have you, and dock...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oksana's Tropical Beach Oasis1 / 22
    (2)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Garden
    • Air Conditioning
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    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2017
    The house is very nice. They are upgrading many of the rooms...the kitchen is really nice. The view is spectacular and the large backyard is great. The fact that they allow...
    Reviewed 1 May 2016
    Our family of 3 couples and 2 singles stayed here in April and loved it. Rental process was smooth, management very nice and provided local info on places to eat and things to...
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    About this property
    Oksana's Tropical Beach Oasis is a spacious ocean front property with spectacular views and a large swimming pool with overflow spa. The beach area has not been dug out by man. We recommend you bring swim shoes to walk around in that area. The dock is currently under repairs after Hurricane Irma...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Charming 3bedroom/2bath home in the Florida Keys1 / 19
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Patio
    • Cable/satellite TV
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    • Waterfront
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2016
    I would recommend this house to anyone the house is clean and comfortable, stocked with evrything you will need. The loacation is perfect, your located about 15 minutes from...
    Reviewed 20 October 2015
    This was a last minute change of plans to rent this home and we could not have been any more pleased. The home was clean, very inviting and I truly felt like I was staying at my...
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    About this property
    Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing, lobstering, diving, and...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This great Vacation Home is conveniently located on Cudjoe Key. The all tile kitchen is fully equipped and living & dining rooms provide ideal entertaining areas for friends and family. Enjoy warm, tropical breezes on the large wood dock, overlooking the deepwater canal, perfect for swimming and...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Dreaming of an awesome Florida Keys vacation? This is your perfect pick! This Cudjoe Key home has everything you could wish for and a perfect vacation spot! The home is designed with rich and warm wood tones making it the perfect place to relax after a long wonderful day of fishing and diving in...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    This home is great for families! It has been recently updated with new tile throughout, new furnishings and bedding, and features 3 bedrooms and 2 bathrooms as well as a roomy loft area. You'll enjoy an open living plan with a nice size full kitchen with plenty of counter room, a dining area as...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Enjoy the rustle of swaying palms and the balmy tropical breezes from the screened and tiled balcony of this immaculate Island home. Home-away-from-home comforts include central air and a well equipped kitchen. The 30' dockage area provides quick and easy access to the best fishing and diving in...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This beautiful, vacation home is tropical, bright and confortable. You'll wish it was your own! The kitchen is fully equipped with all the luxuries of home (and more!). The dockside Tiki Hut and hammock overlook a great, deepwater canal perfect for boating and swimming. This vacation rental home...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Welcome to Egret's Landing! From the private balcony located off the master bedroom living area, to airy and vaulted ceilings, this Cape Cod style home promises all the comforts of home, and so much more! The 40' dock and yard is landscaped with native foliage and offers wandering pathways...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Lafitte Landing is the perfect destination for your Florida Keys vacation. Very nicely appointed 2 bedroom, 2 bathroom canal front home is very comfortable and spacious. This home offers a living-dining-kitchen great room floor plan with comfortable seating and a flat screen TV. Double sliding...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Pet friendly
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    About this property
    Escape from all your cares at this wonderful vacation rental on Cudjoe Key. Just the spot to unwind and let your hair down. There are 3 bedrooms and 3 baths plus a recreation room for the kids to get away. Open and airy living and kitchen area for friends to gather. Full walk around screened...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    It's always 5 O'Clock here at this wonderful Florida Keys vacation spot. Start your day off with refreshing Mimosas or Bloody Marys as you enjoy sitting out on the screened porch overlooking the nice boating canal. The interior is nicely decorated in tropical island style with lovely accents to...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Kick back and relax in this Island vacation home. Or, enjoy the spacious deck located off the kitchen area, and take in the warm tropical breezes, canal and spectacular sunset skies. Fish from the dock or take advantage of the convenient boating access and cruise out to Looe Key, site of some of...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    About this property
    Welcome to Cudjoe Cottage, a wonderful spot to spend your Florida Keys vacation! This 2 bedroom 2 bath home, nestled among lush landscaping, is delightfully decorated in neutral tones with beach accents. The kitchen is completely equipped for the most ardent of chefs, while others may choose to sit...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This Cudjoe Key home is neat as a pin. Brand new in 2007 with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get togethers. The large comfortable living room has plenty of seating including recliners in the sofa and loveseat. Laminate hardwood...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Palm Harbor located at mile marker 23 in Cudjoe Gardens is the perfect spot to unwind and relax in the Florida Keys sunshine. Just minutes from Cudjoe Gardens marina for gas, bait and your fishing needs. Deep draft boating will accommodate up to 4 foot draft. Large and spacious inside with open...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Ocean Views
    • Air Conditioning
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CANAL FRONT HOME WITH 3 BEDROOM AND 2 BATH AND POSSIBLE 4TH BEDROOM , TWO ENTRANCE HOME ONE TO LIVING ROOM AND OTHER TO COVERED DECK OVERLOOKING CANAL. GLASS SLIDERS TO BEAUTIFUL VIEWS OFF 2 BEDROOMS . ALL NEW FURNITURE AND STAINLESS STEEL APPLIANCES, GRANITE COUNTER TOPS AND COFFEE NOOK IN...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Blue Palms Retreat (formerly known as Heron's Roost)1 / 24
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Reviewed 23 August 2018
    The house was clean, up to date, and very comfortable. The furniture under the house was great, as we could sip on cold drinks in the shade and still have a view of the ocean...
    Reviewed 23 August 2018
    We so enjoyed staying at Blue Palms Retreat. The views from the house were simply breathtaking. We enjoyed lounging by the pool and hanging out in the gazaebo. Fishing was...
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    About this property
    This house is a charmer. 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key. Large, heated swimming pool with shaded hang out area and ping pong table. Double kayak and hammock provided. Bikes and paddle boards available for rent. Charming character with hand made pottery...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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