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Cudjoe Key Vacation Rentals

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    Travelers to Cudjoe Key are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    4.5 of 5 bubbles (3) Very good
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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... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 bubbles Reviewed July 17, 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 Key...
    5 of 5 bubbles Reviewed October 20, 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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    3 of 5 bubbles (9) Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 | 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 A/C's 2 queen... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    3 of 5 bubbles Reviewed October 12, 2015
    We love Cudjoe Key and Venture out is a great resort. The unit we stayed in was in need of some repairs, sort of shabby, but clean functional and well stocked. The owner was quick...
    4 of 5 bubbles Reviewed July 23, 2015
    Check-in with resort guard house (this is a gated community) was quick and easy; only accepts cash and checks however for resort fees, so be prepared for that. The rental is just...
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    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. Our home is third from the waters edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool... View all property information
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    Cudjoe Key, Florida Keys 33042
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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... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 19
    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... View all property information
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    Cudjoe Key, Florida Keys
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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... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Location Information
    Cudjoe Key, Florida Keys 33042
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    1 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    For your next Florida Keys vacation, reserve a stay at this waterfront home located on a canal with easy access to either the Atlantic or the Gulf. This home has everything you need to enjoy a relaxing vacation with resort amenities at your backdoor. Featuring 2 bedrooms, 1 bathroom. The master... View all property information
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    Cudjoe Key, Florida Keys 33042
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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... View all property information
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    Cudjoe Key, Florida Keys
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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... View all property information
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    Cudjoe Key, Florida Keys
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    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... View all property information
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    Cudjoe Key, Florida Keys
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    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... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick 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... View all property information
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    Cudjoe Key, Florida Keys 33042
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick 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... View all property information
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    Cudjoe Key, Florida Keys
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    2 of 5 bubbles (1) Poor
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Cute as can be! Tastefully decorated with cozy comfortable furniture. Close to all of the amenities, including the pool, community store, marina, recreation hall, bocce ball courts, etc. Queen bed in one room and a double bed in the second bedroom Nice, large deck on front of home with table and... View all property information
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    Cudjoe Key, Florida Keys
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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... View all property information
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    Cudjoe Key, Florida Keys
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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... View all property information
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    Cudjoe Key, Florida Keys 33042
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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... View all property information
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    Cudjoe Key, Florida Keys
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Relax in this two bedroom, one bath tropically colored vacation home. This home has just been fully remodeled. Lots of windows give it a bright spacious feel. Fun colors and decorations add to its tropical ambiance. Large living room dining area with windows on two sides. Sleeper sofa, rocking... View all property information
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    Cudjoe Key, Florida Keys
    1 / 34
    4.5 of 5 bubbles (48) Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    White Ibis Inn away from the hustle of Key West activities, but close enough to the excitement when you want it and the Atlantic Ocean’s spectacular sunrises, sunsets and endless views of the starry nights. A private Caribbean-style accommodation with adjacent guest house with panoramic view of... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 bubbles Reviewed January 24, 2017
    This house was perfect for our large family to stay. We used the whole property and Kazi was great to work with. We had perfect weather and we had a great time in the pool...
    5 of 5 bubbles Reviewed January 14, 2017
    Kris and Adam both of our fabulous host were fantastic! When we arrived Kris was there to welcome us and made our check-in easy, answered any questions and any issues right away...
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    1 / 16
    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... View all property information
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    Cudjoe Key, Florida Keys
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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... View all property information
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    Cudjoe Key, Florida Keys 33042
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Elegance and Relaxation have been masterfully designed for your stay at this two bedroom, two full bath home located on a canal. There is a 35’dock with posts, cleats, swim ladder and fish cleaning table for the boat you bring or rent. Lounge furniture provided on seawall dock for sunning and... View all property information
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    Cudjoe Key, Florida Keys
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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... View all property information
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    Cudjoe Key, Florida Keys 33042
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    Fresh and clean canal front 2 BD/2 BA vacation home.17’ dock with dock posts, cleat, whip posts and swim ladder.Relax dockside on padded patio furniture with shade umbrella table or up on covered deck's patio furniture with glass sliders leading into living room area. Living room has a 32’ flat... View all property information
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    Cudjoe Key, Florida Keys
    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Cudjoe Key, Florida Keys 33042
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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... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 25
    5 of 5 bubbles (11) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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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.... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    4 of 5 bubbles Reviewed December 8, 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...
    5 of 5 bubbles Reviewed October 16, 2016
    My wife booked this rental property for a long weekend this fall and we were very pleased with the Fandango. Cudjoe Key is pretty much a residential key and doesn't have the...
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    About this property
    AS PER MONROE COUNTY RENTAL LAWS ONLY ONE RENTAL IS ALLOWED PER MONTH TO ONE GROUP OR FAMILY PER 28 Day period. 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.... View all property information
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    Cudjoe Key, Florida Keys 33042
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    About this property
    Canal front, two bedroom, two bath home with relaxing tropical decor and colors. Shaded canal side area with patio furniture for dining or relaxing. For the fisherman a 35' concrete dock/seawall with dock posts, cleats, ladder and fish cleaning table. Florida style living room has glass sliders... View all property information
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    Cudjoe Key, Florida Keys
    1 / 18
    4.5 of 5 bubbles (13) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 18 | Quick View
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    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... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 bubbles Reviewed July 9, 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. It...
    5 of 5 bubbles Reviewed June 18, 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. We...
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    1 / 22
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Designer decorated home located canal front with a 35’ seawall. Seawall comes complete with posts, cleats , fish cleaning table and patio furniture. The inviting living room area has a flat screen TV, a sleeper sofa, rocking recliner easy chair, glass top table with seating for four overlooking... View all property information
    Location Information
    Cudjoe Key, Florida Keys
    5 of 5 bubbles Reviewed April 10, 2017
    Great place and quiet location. Loved the remodeled kitchen with the seating area. We enjoyed the scuba diving @ Looe Key - having a dock for our boat was fantastic. The complex...
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 25
    5 of 5 bubbles (2) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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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. There is a small channel at the end of the dock that... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 bubbles Reviewed January 2, 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...
    5 of 5 bubbles Reviewed May 1, 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 do...
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 bubbles Reviewed January 20, 2017
    This property is fantastic and is actually even better than advertised. Very clean and has amazing ocean views from all rooms. We were three couples renting for a week and had...
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Peace, Privacy, Perfect. This ocean front home has 180 degree wrap porch complete with patio furniture. Large 42' seawall with dock posts, cleats, fish cleaning table, swim ladder and outdoor shower. This home is spacious and well designed for comfort. Front room has 3 sets of double glass sliders... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    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... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 25
    5 of 5 bubbles (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • DVD Player
    • Waterfront
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    2 Bedroom+/2 Bath+ Tropical Paradise Home with floating dock, small beach, heated dipping pool and hot tub. 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... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 bubbles Reviewed March 16, 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...
    5 of 5 bubbles Reviewed July 19, 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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    1 / 22
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Check-out this vacation home! It is situated on the widest canal in Venture Out!! Located on a 35' concrete dock with cleats and dock posts. Beautiful views of the open water from the living room, dining area and kitchen. Recently remodeled, clean fresh decor. Living room has a 49" flat screen 4 K... View all property information
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    Cudjoe Key, Florida Keys 33042
    5 of 5 bubbles Reviewed November 10, 2015
    I have nothing but good things to say about this rental. Sleeps 6, we had three in our group, and more than enough room to stretch out. Comfortable beds, new linens and fresh...
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    1 / 23
    4 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • Ocean Views
    • Air Conditioning
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    • Satellite TV
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Terrace
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    • Pet-friendly
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    • x
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    • x
    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... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 27
    4 of 5 bubbles (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    You will fall in love with the happy colorful tropical decorations in this canal front home. This home offers the fisherman a 35' seawall with high end dock posts, cleats and swim ladder. Lounging furniture to enjoy the seawall view and shade under the home. Covered upper deck has a view of canal,... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 bubbles Reviewed 4 weeks ago
    Clean Comfortable for our family of 4 Close to Key West and neighboring keys Great restaurants near by Safe and convenient development Rented a boat from Maya over on mm 24.5...
    5 of 5 bubbles Reviewed March 31, 2015
    Very nice clean house. Could have used a couple more needed utensils in the kitchen. But, other than that very clean canal, great security, and lots of activities. Great for...
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    1 / 11
    3.5 of 5 bubbles (3) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • ?
    About this property
    Canal front home with spacious ambiance. 35 seawall with dock posts, cleats, fish cleaning table with hose . Covered back deck with ceiling fan, drop shades and patio furniture. Living room has large Flat Screen TV with DVD, sleeper sofa, two rockers, recliner and door to covered deck. Master... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 bubbles Reviewed June 20, 2016
    This was a nice little house for my boys and I. Comfortable and close to all the places we wanted to go. I only wish that we had been advised about the road construction that was...
    5 of 5 bubbles Reviewed July 19, 2015
    We had a very great family vacation. We couldn't have asked for a better place. Everything we wanted and more. We will be back.
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    1 / 24
    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
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    Cudjoe Key, Florida Keys 33042
    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Parking
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    • ?
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    • x
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    Cudjoe Key, Florida Keys 33042
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Washer
    • Patio
    • Satellite TV
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    • Shared Outdoor Pool...
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    Location Information
    Cudjoe Key, Florida Keys 33042
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