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Cudjoe Key Vacation Rentals

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    Travelers to Cudjoe Key are booking May dates now. Secure your vacation rental today, and have the perfect trip.
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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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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Satellite TV
    • DVD Player
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    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    3 Reviews
    3 BedroomsSleeps 6Quick View
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    • Washer
    • Grill
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    • Satellite TV
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    • Waterfront
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent 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...
    Excellent 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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    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
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    1 BedroomSleeps 4Quick View
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    About this property
    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...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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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...
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    Cudjoe Key, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    About this property
    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...
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    Cudjoe Key, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 BedroomsSleeps 6Quick View
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    • Grill
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Retreat to a canal home on the peaceful Cudjoe Island. 25 minuets from Key West, this 3 bedroom home pulls out everyones inner Fisherman. Additional amenities include: dock/boat-slip, coffee maker, stove/oven, stainless steel appliances, 4 private parking spots, large wrap around deck, monthly...
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    Cudjoe Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 of 5 bubbles
    9 Reviews
    2 BedroomsSleeps 6Quick View
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    • Secure Parking
    • Hot Tub
    • Children's Pool
    • Grill
    • Satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Average 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...
    Very good 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...
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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...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Pet friendly
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    Smoking allowed
    About this property
    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...
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    Cudjoe Key, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    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...
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    Cudjoe Key, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Cudjoe Key, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 of 5 bubbles
    2 Reviews
    2 BedroomsSleeps 6Quick View
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    • Hot Tub
    • Internet Access
    • Ocean Views
    • Air Conditioning
    • Washer
    • DVD Player
    • Satellite TV
    • Waterfront
    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...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    1 Review
    1 BedroomSleeps 4Quick View
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    Excellent of 5 bubbles
    Reviewed 2 weeks ago
    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...
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    About this property
    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...
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    Cudjoe Key, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • Wi-Fi
    • Washer
    • DVD Player
    • Ocean Views
    • Waterfront
    • 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 of 5 bubbles
    11 Reviews
    5 BedroomsSleeps 14Quick View
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    • Satellite TV
    • Washer
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good 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...
    Excellent 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
    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
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    4.5 of 5 bubbles
    48 Reviews
    6 BedroomsSleeps 14Quick View
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    • DVD Player
    • Patio
    • Hot Tub
    • Washer
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent 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...
    Excellent 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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    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...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    5 of 5 bubbles
    1 Review
    2 BedroomsSleeps 6Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    2 Reviews
    5 BedroomsSleeps 14Quick View
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    • Private Outdoor Pool (Heated)
    • Private Yard
    • Air Conditioning
    • Parking
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent 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...
    Excellent 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...
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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...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    5 of 5 bubbles
    10 Reviews
    2 BedroomsSleeps 6Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • DVD Player
    • Waterfront
    • Satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent 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...
    Excellent 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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    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...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 of 5 bubbles
    1 Review
    2 BedroomsSleeps 4Quick View
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    About this property
    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...
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    Cudjoe Key, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    • DVD Player
    • Hot Tub
    • Terrace
    • Grill
    • Patio
    • Washer
    • 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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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 of 5 bubbles
    3 Reviews
    2 BedroomsSleeps 6Quick View
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    Smoking allowed
    Average of 5 bubbles
    Reviewed July 12, 2016
    Great location, but this is a RV park and has rules and limited parking. The general store has everything you need, Ice to fuel and ramps have a water to wash and flush. Easy...
    Very good of 5 bubbles
    Reviewed October 27, 2014
    Enjoyed our stay. Lots to see and do! The view was breathtaking and the resort was in a great location. The pools and hot tub were very convenient. We would definitely visit again!
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    About this property
    Panoramic open water view! Enjoy million dollar ocean view from deck, living room, dining area and kitchen. Unusually large 50' seawall with cleats for your boat, dock area also has a swim ladder and fish cleaning table. Living room area has a Flat screen TV conveniently placed for viewing from...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    13 Reviews
    6 BedroomsSleeps 18Quick View
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    • Washer
    • Satellite TV
    • Air Conditioning
    • Porch
    • Grill
    • Internet Access
    • Waterfront
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent 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...
    Excellent 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...
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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
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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    • Balcony
    • Parking
    • Wi-Fi
    • Terrace
    • Grill
    • Ocean Views
    • Air Conditioning
    • Hot Tub
    Suitability
    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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    Cudjoe Key, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.5 of 5 bubbles
    3 Reviews
    2 BedroomsSleeps 5Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent 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...
    Excellent 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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    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...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 of 5 bubbles
    1 Review
    2 BedroomsSleeps 6Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent 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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    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...
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    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.5 of 5 bubbles
    4 Reviews
    2 BedroomsSleeps 6Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 3 days 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...
    Excellent 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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    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,...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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