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Vacation Rentals in Cudjoe Key, FL

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    Travelers to Cudjoe Key are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 54
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 22
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 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...
    5 of 5 bubbles Reviewed April 13, 2016
    Our second trip to the keys; this property met our expectations in full. Renting it was hassle free. Moreover, the owner quickly responded to question before, during and after the...
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    1 / 22
    3.5 of 5 bubbles (10) Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Secure Parking
    • Hot Tub
    • Children's Pool
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    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
    5 of 5 bubbles Reviewed February 3, 2016
    This was our third or fourth stay at Cottage by the sea, a comfortable place to stay, the weather was disappointing this year, 5" of rain, wind and cold to 58 degrees. And then...
    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...
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    1 / 19
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
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    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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    1 / 12
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Parking
    • Wi-Fi
    • Terrace
    • Grill
    • Ocean Views
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    • x
    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 / 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
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Palm Harbor located at mile marker 23 in Cudjoe Gardens is the perfect spot to unwind and relax in the Florida Keys sunshine. Just minutes from Cudjoe Gardens marina for gas, bait and your fishing needs. Deep draft boating will accommodate up to 4 foot draft. Large and spacious inside with open... View all property information
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    Cudjoe Key, Florida Keys
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    1 / 34
    4.5 of 5 bubbles (46) 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 3 weeks ago
    We loved both houses. Place was clean and very convenient to the keys!!! Pool was refreshing and relaxing. Definitely planning our next trip here to stay again. Chris the...
    5 of 5 bubbles Reviewed October 27, 2016
    What a great place to stay with a group of friends. There is plenty of space and the owner is one of the nicest and attentive people you could ever meet. The ammenities are very...
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    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Porch
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    • x
    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
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    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
    1 / 15
    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... View all property information
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    Cudjoe Key, Florida Keys
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    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
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
    1 / 8
    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
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Porch
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    • x
    About this property
    It's always 5 O'Clock here at this wonderful Florida Keys vacation spot. Start your day off with refreshing Mimosas or Bloody Marys as you enjoy sitting out on the screened porch overlooking the nice boating canal. The interior is nicely decorated in tropical island style with lovely accents to... View all property information
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    Cudjoe Key, Florida Keys
    1 / 22
    5 of 5 bubbles (10) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
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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
    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...
    5 of 5 bubbles Reviewed July 1, 2016
    Our family recently stayed at this home. Home was perfect , more than enough stuff for a family to do. Not including only 20 miles from Key West. Had 1 small , minor issue and...
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    1 / 15
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Private Outdoor...
    • Private Yard
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    4 bedroom/3 bath Ocean Front home on Cudjoe Key with; heated pool with attached spa, boat dock, 2 screened in porches, kayaks and spectacular ocean views. Sleeps 10+ Master Bedroom: King bed, bath with shower and tub. TV Second Bedroom: Queen bed, hall bath with tub/shower. Third Bedroom: King... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    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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    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    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 / 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 / 27
    3.5 of 5 bubbles (3) Average
    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
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    Cudjoe Key, Florida Keys 33042
    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...
    4 of 5 bubbles Reviewed January 3, 2015
    Nice property on a friendly resort. Goods and bad points:- Small shop with a simple selection of key essentials Onsite parking underneath the property Plenty of storage No...
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    1 / 21
    3.5 of 5 bubbles (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Cudjoe Key, Florida Keys 33042
    3 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...
    4 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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    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 / 11
    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... View all property information
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    Cudjoe Key, Florida Keys
    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
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    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
    1 / 21
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Relax enjoying water views from both front and back decks. This home was recently redecorated with comfy upscale furniture and art. Large open living room has flat screen TV with DVD. Furniture is large and comfortable, sleeper sofa, love seat and armchair with hassock. Kitchen is conveniently laid... View all property information
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    Cudjoe Key, Florida Keys 33042
    5 of 5 bubbles Reviewed November 10, 2014
    We had a wonderful stay at Venture Out. It was very peaceful and enjoyable. The internet was fast and the cable TV had plenty of channels. The appliances and furniture are modern...
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    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • ?
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    • 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
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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 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 / 20
    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 35dock 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
    1 / 19
    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
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    Cudjoe Key, Florida Keys
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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... View all property information
    Location Information
    Cudjoe Key, Florida Keys
    1 / 11
    4.5 of 5 bubbles (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Washer
    • Air Conditioning
    • Parking
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    For a TROPICAL VACATION come to our beautiful designer furnished 2BD/2BA cottage at VENTURE OUT RESORT on Cudjoe Key. We pride our home on its comfort and cleanliness and have been told we have one of the nicest 2BD/2BA NON-WATERFRONT RENTAL HOMES in Venture Out Resorts. Olympic size pool, hot... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 bubbles Reviewed February 28, 2016
    We stayed here for the month of February 2016, and were very pleased with our experience. The unit is well laid out, had a modern renovated kitchen, updated bathrooms, and great...
    3 of 5 bubbles Reviewed July 18, 2015
    This place is fine if you do not mind small. This is a small mobile home close to water in a large community. The place was not real clean, mostly the floors were dirty and our...
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    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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... View all property information
    Location Information
    Cudjoe Key, Florida Keys
    1 / 11
    3.5 of 5 bubbles (3) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Amenities & Details
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    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
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Private Outdoor...
    • Terrace
    • Air Conditioning
    • Internet Access
    • Washer
    • Balcony
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    3 Bedrooms, 3 Bathrooms, Sleeps 8 L’Anquesa – The Angel’s Key Luxury Amenities Include: Total renovation completed January 2014 2 master bedrooms suites with king beds, ensuite baths, flatscreen TVs and surround sound with incredible panoramic views 1 Guest room with 2 Queen Beds... View all property information
    Location Information
    Cudjoe Key, Florida Keys
    5 of 5 bubbles Reviewed March 31, 2016
    L'Anquesa is a perfect destination for decompressing from the grind. Your art is the ocean and it can be seen from everywhere in the home. Attention to detail was perfect and...
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    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This 5 bedroom 3 bath house with pool on ocean front property on Highway, located just 20 miles away from the famous Key west complete with WiFi. This lovely home has it's own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill,... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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... View all property information
    Location Information
    Cudjoe Key, Florida Keys