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Vacation Rentals in Sugarloaf Key, FL and nearby

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    1 / 42
    Sugarloaf Key
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    The following rentals are within 5 miles of Sugarloaf Key, Florida Keys, Florida.

    1 / 24
    Cudjoe Key
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 25
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 54
    Cudjoe Key
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Patio
    • Washer
    • DVD Player
    • Balcony
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    • Pet-friendly
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    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
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Private Outdoor...
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    • Waterfront
    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    WATERFRONT POOL HOME, MINUTES TO KEY WEST, CONVIENT TO RESTATURANTS AND LOCAL ATTRACTIONS. A perfect vacation get away. But please note we only rent weeks from Saturday to Saturday. Three separate living/sleeping areas. 1)Main house is fully appointed with flat screen TV, DVD, DVR, Comcast cable,... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 27
    4 of 5 stars (1) Very good
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    • Sauna
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    • x
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    • x
    About this property
    For your next escape to the Florida Keys, reserve a stay at this delightful waterfront Cudjoe Key vacation rental home. Perfectly situated on a canal with easy access to the area’s most notable attractions, this serene house has everything you need for a relaxing island retreat! Featuring 2... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33462
    4 of 5 stars Reviewed July 13, 2016
    The rental was as advertised. The location was great with easy access to great snorkeling and fishing. Great location to moor a boat. Be advised there is an additional charge of...
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    1 / 22
    3.5 of 5 stars (10) Average
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Secure Parking
    • Hot Tub
    • Children's Pool
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    • 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
    5 of 5 stars 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 stars 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 / 12
    5 of 5 stars (1) Excellent
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Peace, Privacy, Perfect. This ocean front home has 180 degree wrap porch complete with patio furniture. Large 42' seawall with dock posts, cleats, fish cleaning table, swim ladder and outdoor shower. This home is spacious and well designed for comfort. Front room has 3 sets of double glass sliders... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 28
    Cudjoe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Parking
    • Wi-Fi
    • Terrace
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    • Ocean Views
    • Air Conditioning
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    • 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
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    Cudjoe Key, Florida Keys 33042
    1 / 15
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Canal front home on spacious double lot, interior has been remodeled to feature comfort with designer touches. 32’seawall complete with posts, cleats, swim ladder, fish cleaning table and waterhose. Great views of the canal can be enjoyed from many spots including a bench on seawall, the covered... View all property information
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    Cudjoe Key, Florida Keys
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    1 / 24
    5 of 5 stars (1) Excellent
    Cudjoe Key
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Terrace
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    • Pet-friendly
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    • x
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    • 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 stars 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 / 13
    Cudjoe Key
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This home features stunning Open Water Views from upper level covered deck, living room, dining area and dock! Upstairs large deck overlooks the open water; streetside deck is perfect for relaxing, and enjoying the evening breezes. Shaded patio/dock area complete with tropical decor furniture... View all property information
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    Cudjoe Key, Florida Keys
    1 / 8
    2 of 5 stars (1) Poor
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick 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... 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
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    Cudjoe Key, Florida Keys 33042
    1 / 7
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Description: 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... View all property information
    Location Information
    Cudjoe Key, Florida Keys
    1 / 19
    4.5 of 5 stars (3) Very good
    Cudjoe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Grill
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    • Satellite TV
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    • Waterfront
    • Air Conditioning
    • DVD Player
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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 stars 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 stars 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 / 16
    3 of 5 stars (1) Average
    Cudjoe Key
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
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    • ?
    About this property
    Canal front home with 35 seawall. Dock side complete with whips, posts, cleats, swim ladder and mosaic picnic table. Relax canal side under shade awning on patio furniture and soft folding chairs and recliner. Glass sliders leading into bright open Florida style living room which has flat screen TV... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    3 of 5 stars Reviewed March 18, 2016
    This small, quirky little trailer met our basic needs. Not a place I would rent if I needed it for more than a place to sleep and shower. The community is clean, friendly and...
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    1 / 13
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Two bedroom home with ocean view from living room and deck. Living room has a queen size sleeper sofa, flat screen TV.Smart TV with Wifi for your devices. Kitchen is open and inviting with wood tone cabinets. Dining area located in a pleasant alcove near kitchen has a glass top table with seating... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 11
    3.5 of 5 stars (3) Average
    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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    About this property
    You will fall in love with the happy colorful tropical decorations in this canal front home. 35' seawall with whips, high end dock posts, cleats, swim ladder. Large table, comfortable patio chairs and lounging furniture to enjoy the seawall view and shade under the home. Upper deck has a view of... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 stars 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 stars 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 / 22
    5 of 5 stars (9) Excellent
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • DVD Player
    • Waterfront
    • Satellite TV
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    2 Bedroom+/2 Bath+ Tropical Paradise Home with floating dock, small beach, heated dipping pool and hot tub. This has been a popular honeymoon and anniversary celebration home for over 10 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even have to get out of... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 stars 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 stars 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 / 21
    3.5 of 5 stars (2) Average
    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 stars 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 stars 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 / 34
    4.5 of 5 stars (42) Very good
    Cudjoe Key
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
    About this property
    Please note that we are totally revamping our property during the month of August. Upgrades include improving the swimming pool, replacing furniture, and significant improvements of the landscaping. Please visit us at White Ibis Inn soon to see the brand new look of our property. White Ibis Inn... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 stars Reviewed 2 weeks ago
    This was our family's first trip to Florida keys and I don't think we could have chosen a better place than White Ibis Inn. The location is right between Bahia Honda beach and Key...
    4 of 5 stars Reviewed December 30, 2015
    We came with a very large group of family for our daughters wedding. While making reservations we decided we didn't want to be in all the noise and rat race of bust Key West...
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    1 / 15
    5 of 5 stars (1) 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
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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 stars 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 / 20
    5 of 5 stars (9) Excellent
    Cudjoe Key
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
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    • Private Outdoor...
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    • Pet-friendly
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    • 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
    5 of 5 stars 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...
    5 of 5 stars Reviewed September 12, 2015
    This property really is wonderful. We had a fantastic 10 days here an would come back in a heart beat! The house has breath taking ocean views especially from the master bed and...
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    1 / 22
    5 of 5 stars (1) Excellent
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 40' flat screen TV... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 stars 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 / 15
    4 of 5 stars (1) Very good
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Freshly redecorated canal front home. Living room has a 32 flat screen TV with DVD and two sleeper sofas. Master bedroom has full size bed, mirror closet and a vanity with drawers. Guest bedroom has twin size trundle bed with mirror closet and slider doors to patio and canal. Spacious open kitchen... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    4 of 5 stars Reviewed November 23, 2013
    Two bedrooms, living room, full kitchen and bathroom was enough to accommodate five people. Place is quiet, but not very close to public beaches. For the end of October there are...
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    1 / 19
    4.5 of 5 stars (13) Very good
    Cudjoe Key
    6 Bedrooms, 4 Bathrooms, Sleeps 18 | Quick View
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    • Washer
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    • Air Conditioning
    • Porch
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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
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    Cudjoe Key, Florida Keys 33042
    5 of 5 stars 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 stars 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 stars (1) Excellent
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
    Location Information
    Cudjoe Key, Florida Keys 33042
    5 of 5 stars 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 / 11
    4.5 of 5 stars (4) Very good
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • ?
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    • 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 stars 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 stars 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 / 24
    Cudjoe Key
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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