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Cudjoe Key Holiday Rentals

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    Travellers to Cudjoe Key are booking December 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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Oceanview Estate 15 minutes from Key West - 6 bedroom accommodate 13 guests1 / 34
    (48)Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • Waterfront
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    • Central Heating
    • Ocean Views
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful Ocean view, on a canal, three lots from open water in Venture Out Resort; a safe, gated community. Park your boat or kayak right outside your front door on the canal, or just relax and enjoy your mosaic picnic table and 4 patio chairs, and Weber charcoal BBQ. Only 7 steps up or down to...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fandango1 / 25
    (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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    Cudjoe Key, Florida Keys 33042
    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
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    • Waterfront
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    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 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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    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • DVD Player
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Family Retreat ocean front home with private pool1 / 18
    (13)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2016
    The house is designed perfectly for a mixed aged family group. Lots of separate areas for different activities and also a large area for the whole group to celebrate together...
    Reviewed 18 June 2015
    12 of our family came down from NC & VA to celebrate a college graduation and fulfill some bucket list items. It was a classic road trip and the very best vacation imaginable...
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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. Floating dock is great to fish and swim...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    ** Contact for special rates ** The minimal rental is a WEEK but once you book a partial month, the entire month is to be blocked off. THESE are not our laws but laws from MONROE county we need to abide by them. The rates FOR A WEEK, 2 WEEKS are posted below at the bottom of the description....
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    Cudjoe Key, Florida Keys 33042
    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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    • DVD Player
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    • Terrace
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    • Balcony
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    Pet friendly
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    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    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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    Cudjoe Key, Florida Keys 33042
    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
    Come enjoy the best the Florida Keys has to offer, with this lovely 3 bedroom and 2 bathroom canal front home on Cudjoe Key! This nautically decorated, comfortable home offers quick boating access to Cudjoe Bay from the 40’ dock and is fully equipped for the water enthusiast with provided kayaks...
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    Cudjoe Key, Florida Keys 33042
    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    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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    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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    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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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    Cudjoe Key, Florida Keys 33042
    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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    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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    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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    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Come and enjoy the wonderful Florida Keys lifestyle at Tropical Bay. Located at mile marker 22, close to Key West and Marathon for great day trips around the islands. This spacious 3 bedroom, 2 bathroom ground level home is cozy and comfortable. Extra large screened porch overlooks a peaceful canal...
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    Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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    • Waterfront
    • Cable/satellite TV
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    • Air Conditioning
    • Hot Tub
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    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
    2 Bedroom+/2 Bath+ Tropical Paradise Home with floating dock, small beach & heated dipping pool. This has been a popular honeymoon and anniversary celebration home for over 10 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even have to get out of bed. This...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
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    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Blue Adventure Waterfront at Venture Out1 / 23
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Ocean Views
    • Children's Pool
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    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Balcony
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    About this property
    Head to Cudjoe Key and revel in upscale Florida comfort in this three-bedroom, two-bath home for six. Lounge by your private pool and leave your cares behind. Located right on a canal and within walking distance to the Gulf and ocean, you'll be able to enjoy a sunny, water-focused vacation. Also...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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