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Cudjoe Key Family & Kid Friendly Rentals

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    Travelers to Cudjoe Key are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    65 Matching Rentals in Cudjoe KeyView all 93 rentals
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    Smoking allowed
    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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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Family Retreat ocean front home with private pool1 / 25
    (16)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 May 1, 2019
    Our 3 generation family of 7 stayed at Family Retreat in April 2019. The house is perfect for the 2 married couples, 1 single person, and 2 teenage boys. We used 5 of the 6...
    Reviewed June 11, 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.
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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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    Cudjoe Key, Florida Keys 33042
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 18
    Fandango1 / 32
    (12)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Waterfront
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 8, 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 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...
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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
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Oceanview Estate 15 minutes from Key West - 6 bedroom accommodate 13 guests1 / 56
    (50)Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2019
    So glad we booked this lovely home. All three generations had a fabulous time and used all the facilities this rental offers. This 6 BR craftsman house and cottage was the...
    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...
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    About this property
    We are 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. We have one of a kind property in the Florida Keys with custom built fence, gated, quiet and...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 14
    Tropical Paradise Oceanfront Home with Pool1 / 25
    (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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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Cudjoe Key, Florida Keys 33043
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Oksana's Tropical Beach Oasis1 / 34
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Yard
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    About this property
    This is an older home that has been previously remodeled and updated. The carpets are due for replacement, and scheduled to be replaced in the 2020. We are continuing to update this home and are in the process of bringing it up to a higher standard. Current condition of this beautiful home will...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful house nestled far off of US 1. Rent one or both of our other properties that are within feet of each other for a great full family vacation. Nice water view over Cudjoe Bay, comes with water access for a small boat with options to dock larger and multiple boats nearby at no extra cost....
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated 3 bedroom/2 bath home sleeps 8. Enjoy early morning coffee or evenings gazing at the stars from the cozy balcony. Downstairs area also has space for relaxing, grilling or simply putting all your fishing equipment together. Our Island House is on a canal leading within minutes to...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Charming 3bedroom/2bath home in the Florida Keys1 / 21
    (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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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely remodeled canal-front home on Cudjoe Key. Remodel includes new floors throughout (bamboo hardwood and tile), chef's kitchen with island and stainless appliances, ceiling fans throughout and new a/c. Brand new couch and chair (not pictured). The house has a new roof, stairs, siding,...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Patio
    • Washer
    • Grill
    • Terrace
    • Balcony
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come get your day made at “Make My Day.” This ground level home offers 2 bedrooms, den with a queen sleeper sofa, a well-equipped kitchen and cozy living room. While enjoying the comforts of inside open the double French doors and let the open water breezes blow your worries away. Step out on to...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    • Terrace
    • Patio
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    • Balcony
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay at this heavenly oasis. Pull up to a fully fenced 2 bedroom, 2 bathroom Florida Keys home. The front parking area provides parking for you AND your guests. In addition, there is plenty of space to park your water toys on the 60’ of dockage. The home offers beautfiul, vaulted wood...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Ocean Views
    • Balcony
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay at this tropical style 2 bedroom, 2 bathroom home in Venture Out. Located in a gated community with all the amenities you will need for any Florida Keys vacation, including a marina with a store, 2 boat ramps, and easy access to the Gulf or Atlantic Ocean side. When you are not boating,...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Blue Palms Retreat (formerly known as Heron's Roost)1 / 33
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 9, 2019
    This is our second year staying at Blue Palms and we would do it again! This is our 7th year traveling to the Keys for our family vacation. We had our family of four and...
    Reviewed August 23, 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...
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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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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Paradise in the Lower Keys!1 / 34
    (12)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    * OCEAN FRONT *56' PRIVATE DOCKAGE * 5 to 7 night min. 2Bd/2Ba Sleeps 4 + 2 Kids1 / 42
    (72)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 5, 2019
    Wow! Ocean views all around. Magnificent sunrises right from the deck. I am typically a beach person and love Cudjoe Key because it is about 40 minutes to Fort Zachary Taylor...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Blue Vacation Home, private heated pool, boat dock.1 / 50
    (42)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed November 1, 2019
    We just returned home from a wonderful vacation!! The house was clean and in a great location! The pool was perfect for the kids. We were extremely happy with our stay and will...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Luxurious Oceanfront Home on Beach w/Heated Pool, Dock, Kayaks, Bikes, Fire Pit1 / 50
    (69)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Private Cottage with Pool and Dock1 / 19
    (34)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Cudjoe Cottages, swimming pool, kayaks, 20 miles from Key West1 / 27
    (14)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Water Front Beautiful Home1 / 47
    (55)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Cozy and modern island living, Cudjoe Key1 / 23
    (13)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Paradise Awaits, Stilt home on Canal for fisherman,or Rest and Relaxation1 / 50
    (15)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
    Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West1 / 23
    (87)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Venture Out #465 2/2 Tropical Getaway on Canal with Open Water View1 / 24
    (22)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Crystal Clear Water Getaway!1 / 33
    (15)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Private heated Pool, perfect location, boat dock. Tent sites.1 / 46
    (38)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful home in oceanfront resort with pool & dock, 16 miles from Key West1 / 17
    (71)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Sparkling Clean & New Turn Key 1Bd/1Ba1 / 21
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access.1 / 36
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Direct Oceanfront - Atlantic Side - Dockage - Swimming Pool - Kayak1 / 16
    (46)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Cottage with Pool and Dockage, just minutes to Key West1 / 18
    (30)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    BIG BLUE waits for you in the sunny Keys1 / 49
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Just 20 miles from Key West!  Oceanfront, dockage, kayaks, swimming pool1 / 21
    (14)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Resort Waterfront Home1 / 29
    (35)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    MAGNIFICENT OCEAN VIEW w/35' of DOCKAGE!! Many activities. Great Rates for 2019!1 / 22
    (48)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Venture Out - Waterfront Paradise   2/1, with  35' Dock and open water views!1 / 38
    (69)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Cottage with Pool, Kayaks, and Boat Dockage just minutes to Key West!1 / 17
    (24)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Reviewed September 2, 2017
    I rented this cottage for my husband's birthday. Awesome location. There was a mix up when we arrived but the owner came right over and cleaned the unit for us and had it...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    OCEAN FRONT: The Glass House1 / 48
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Fishermen’s paradise � CHRISTMAS SPECIALS!1 / 38
    (13)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    1
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