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Vacation Rentals in Sugarloaf Key, FL and nearby

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    1 / 8
    Sugarloaf Key
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    1 / 12
    Sugarloaf Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    Sugarloaf Key
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    1 / 23
    Sugarloaf Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Balcony
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    • Patio
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    • ?
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    • x
    Location Information
    Sugarloaf Key, Florida Keys 33042
    1 / 24
    Sugarloaf Key
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    Sugarloaf Key, Florida Keys 33042
    1 / 23
    Sugarloaf Key
    5 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Patio
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    • x
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    • x
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    Sugarloaf Key, Florida Keys 33042
    1 / 24
    Sugarloaf Key
    3 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    Location Information
    Sugarloaf Key, Florida Keys 33042

    The following rentals are within 5 miles of Sugarloaf Key, Florida Keys, Florida.

    1 / 25
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • x
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    • x
    About this property
    Venture Out Unit 411 is a waterfront unit with 35' of dock space and Wi-Fi internet access that will provide you with all of the comforts of home. Rather than be cramped into a simplistic motel room, you'll have all of the benefits of having a kitchen, dining room, living room, two bedrooms, two... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 54
    Cudjoe Key
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Patio
    • Washer
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Waterfront 120' Dock - Extensive Tropical Gardens Abound - Privacy - New Stainless Steel Appliances - 3 Bedrooms - Home Newly Remodeled and Redecorated - 300 sq' Elevated Deck - Pets Welcome w/ Fenced Backyard - New Bathroom Featuring Large 3 Head Shower - New King Size Sleep Number Bed - Fully... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 24
    Cudjoe Key
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Shared Outdoor Pool...
    • Wi-Fi
    • Ocean Views
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Cudjoe Key, Florida Keys 33042
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    1 / 19
    4.5 of 5 bubbles (3) Very good
    Cudjoe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Grill
    • Patio
    • Satellite TV
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    • Waterfront
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    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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    1 / 28
    Cudjoe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Parking
    • Wi-Fi
    • Terrace
    • Grill
    • Ocean Views
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 21
    Cudjoe Key
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
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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... View all property information
    Location Information
    Cudjoe Key, Florida Keys
    1 / 22
    3 of 5 bubbles (9) Average
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Secure Parking
    • Hot Tub
    • Children's Pool
    • Grill
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    • Washer
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    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 10
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • ?
    About this property
    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
    Location Information
    Cudjoe Key, Florida Keys
    1 / 20
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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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... View all property information
    Location Information
    Cudjoe Key, Florida Keys
    1 / 23
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    • 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
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 23
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
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    • x
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    • ?
    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... View all property information
    Location Information
    Cudjoe Key, Florida Keys
    1 / 19
    Cudjoe Key
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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... View all property information
    Location Information
    Cudjoe Key, Florida Keys
    1 / 23
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    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
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    1 / 16
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Pet-friendly
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    • x
    • ?
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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
    Location Information
    Cudjoe Key, Florida Keys
    1 / 22
    5 of 5 bubbles (9) Excellent
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Internet Access
    • DVD Player
    • Waterfront
    • Satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    Suitability
    • 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 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 / 12
    5 of 5 bubbles (1) Excellent
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 8
    2 of 5 bubbles (1) Poor
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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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... View all property information
    Location Information
    Cudjoe Key, Florida Keys
    1 / 16
    5 of 5 bubbles (2) Excellent
    Cudjoe Key
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Private Outdoor...
    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • 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 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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    1 / 18
    4.5 of 5 bubbles (13) Very good
    Cudjoe Key
    6 Bedrooms, 4 Bathrooms, Sleeps 18 | Quick View
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    • Washer
    • Satellite TV
    • Air Conditioning
    • Porch
    • Grill
    • Internet Access
    • Waterfront
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    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... 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 / 21
    5 of 5 bubbles (11) Excellent
    Cudjoe Key
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
    • Washer
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    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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    1 / 21
    4 of 5 bubbles (3) Very good
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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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... View all property information
    Location Information
    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 / 27
    3.5 of 5 bubbles (3) Average
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
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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 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 / 11
    3.5 of 5 bubbles (3) Average
    Cudjoe Key
    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 / 22
    5 of 5 bubbles (1) Excellent
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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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
    Location Information
    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 / 34
    4.5 of 5 bubbles (48) Very good
    Cudjoe Key
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
    • Patio
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    • Private Outdoor...
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    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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 4 weeks ago
    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 / 37
    Sugarloaf
    2 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    About this property
    Tropical Oceanfront resort style home in Bay Point, Florida Keys just off mile marker 15 on your very own beachfront 1 acre piece of heaven. Enjoy a beautiful open great room, large sundeck and patio area with views where the ocean meets the sky. Chill out by your lagoon style pool or catch some of... View all property information
    Location Information
    Sugarloaf, Florida Keys 33040
    1 / 12
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Washer
    • DVD Player
    • Ocean Views
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Cudjoe Key, Florida Keys 33042
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    Cudjoe Key
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 20
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Hot Tub
    • Terrace
    • Grill
    • Patio
    • Washer
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Cudjoe Key, Florida Keys 33042
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