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Holiday Homes in Sugarloaf Key

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    Don't let other travellers get your favourite Sugarloaf Key area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 92 Rentals in Sugarloaf Key
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    Sugarloaf Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 15 kilometres of Sugarloaf Key.
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Waterfront Cozy Camper with Boat Ramp & Dock!1 / 15
    (1)Excellent
    Little Torch Key
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Tropical Blue Adventure Waterfront at Venture Out1 / 29
    (2)Very good
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Children's Pool
    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 you, and dock...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cudjoe Key
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes, is located right in the center of the Lower Keys. Key West is only 16 miles in one direction and Marathon 25 miles in the other. This 1200...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sugarloaf
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Balcony
    • Waterfront
    • Terrace
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This pet-friendly home completed in 2012 has 5 rooms, 3 king size beds, and 4 twins plus a twin sofa bed and three full bathrooms. The home has a huge kitchen with custom made wood cabinets and top of the line stainless steel appliances including an indoor gas grill and a standing freezer: to keep...
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    33042, Sugarloaf, Florida Keys
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    Little Torch Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise! Come experience the amazing Keys and beautiful open water home with ramp and long dock for your boat. Consider it a must-see rustic outdoor environment during fishing trap season, very typical in the Keys! The private lot is .68 acre with one other rental and still very...
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    33042, Little Torch Key, Lower Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a spacious, open floor plan, Three bedrooms, Two Bathrooms, 6 people accomodation, brightly painted colors, beautifully furnished. Relax in the upper covered porch or down below to the open and spacious patio leading to the pool. Outdoor Tiki shower hut. The grounds are landscaped with an...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cudjoe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Little Torch Key
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Waterfront
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 BR, 2 BA home offers so many special features all in one perfect location! Situated around the corner from Dolphin Marina, a quick 60 second trip down the canal puts you directly to open water offering access to both the Gulf and Ocean. The canal has a depth of 8-10 ft which can accommodate...
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    33042, Little Torch Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Pirates Pointe1 / 18
    (1)Excellent
    Little Torch Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2016
    Excellent !!! I rented this house for a month last fall and didn't want to leave. I towed a boat down from NC and docked it in the canal right behind the house. Part of my...
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    About this property
    Here is the hidden treasure you have been looking for. Pirates Pointe is a great get a way for you and the family. Located in the Jolly Rodger subdivision at mile marker 28 which boasts excellent deep draft boating. Dolphin Marina is located at the entrance to the subdivision making it easy to...
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    33042, Little Torch Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the ultimate peace and quiet offered on Big Torch Key. Located just 5 miles off the Overseas Highway. This pristine area is a true treasure of the lower Keys. This home is nicely remodeled and boasts large spacious room and comfortable furnishing. The shady screened porch overlooks the...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Little Torch Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Anchors Away vacation home on Big Pine Key. A simply delightful and cozy home. The exterior is out of this world with a large heated swimming pool, large double outdoor shower and beautiful dock area .The interior is recently updated with hardwood floors and soothing colors. The kitchen...
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    33043, Little Torch Key, Lower Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sugarloaf
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second...
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    33040, Sugarloaf, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Casa Del Sol1 / 15
    (1)Average
    Ramrod Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2017
    My wife and I rented this home for September of 2016. We rented it mainly because it was pet friendly and had a nice view. We paddle board so the location was perfect. The...
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    About this property
    Sit back and relax in this delightful home, situated on the open water. The entire rear wall of this home is glass for endless views of the blue-green waters of the Florida Keys. Equipped with all the comforts of home plus a heated pool. The open porch catches the breeze, and the tropical setting...
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    33042, Ramrod Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
    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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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ramrod Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Tree House on Ramrod Key. This home is a  delightful Florida Keys get-a-way. This home is roomy and spacious to please the whole family. The combination kitchen, dining and living room is just perfect for everyone to gather around and make super cocktails and snacks while planning...
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    33042, Ramrod Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    • Washer
    • Waterfront
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It’s more than just another Day in Paradise, it’s an incredibly wonderful and memorable vacation stay in the fabulous Florida Keys! Please come stay with us in this large 3 bed 3 bath heated and chilled pool home on deep water canal in Summerland Key. Entering the home by way of the 2 story Great...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cudjoe Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Summerland Key
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Patio
    • Ocean Views
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Casa Manana,' the name affectionately assigned this beautiful gated property in Summerland (Ramrod) Key, is a uniquely situated private waterfront venue. Enter through the gates and you will immediately be transported into the tranquil, easygoing and thoroughly relaxing Keys lifestyle. Located on...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Cudjoe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dreaming of an awesome Florida Keys vacation? This is your perfect pick! This Cudjoe Key home has everything you could wish for and a perfect vacation spot! The home is designed with rich and warm wood tones making it the perfect place to relax after a long wonderful day of fishing and diving in...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Little Torch Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Simple and sweet with no muss, no fuss. It's all right here - Gulf Side! This quaint two bedroom vacation home offers views, a deep-water boating and swimming canal and a protective seawall. This home offers 2 queen-size beds and an additional sleeper sofa. A glassed-in porch and all the other...
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    33043, Little Torch Key, Lower Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Little Torch Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Manatee Bay located in the Port Pine Height area is just the right spot to bring your family and friends for an unbelievable Keys vacation. Great Gulf-side boating is at your fingertips and just a short run out to the Atlantic to fish and dive all the great reef spots. The gulf side waters are full...
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    33043, Little Torch Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Little Torch Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set sail for a glorious Florida Keys vacation at the Blue Marlin. Spacious and comfortable for 6 people in this 3 bedroom, 2 bath, Little Torch Key home. Located down a private lane and overlooking the crystal blue waters of Pine Channel, gulf side. All the rooms are spacious and decorated in...
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    33042, Little Torch Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront House1 / 51
    (1)Excellent
    Summerland Key
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Garden
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2018
    What a find in renting this home. It’s one of the nicest we have stayed in since coming to the Keys. From the owner’s, to the manager, to the pool guy, to the grounds’ keeper...
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    About this property
    This luxurious, but cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands, the most prominent of which is Looe Key reef, a popular diving/snorkeling area. (There is an island, located a few miles out directly in front of the home, was formerly...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Fandango1 / 60
    (12)Excellent
    Cudjoe Key
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Waterfront
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2017
    Our family and friends had an amazing week at Fandango. Everything from the location, to the amenities was perfect. The house had all you needed to create unforgettable family...
    Reviewed 8 December 2016
    My daughter-in-law leased Fandango House for 3 days to celebrate the birthdays of my two children and myself. Fandango is a beautifully kept vacation rental that has all the...
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    About this property
    Designed as the ultimate vacation rental. Five Bedroom/Three Bath Oceanview Home with Heated Pool and Hot Tub. Panoramic Ocean Views. Sleeps 10+. Located on Cudjoe Key. Includes private boat dock, private beach, kayaks, and bikes. Weber BBQ grill, Lot's of lounge chairs and two hammocks....
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Family Retreat ocean front home with private pool1 / 25
    (15)Very good
    Cudjoe Key
    6 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2018
    Nice large house with plenty of space .Not much Beach or Access to fishing without a Boat as the water is very shallow in this whole area. Easy drive to whatever you are wanting.
    Reviewed 21 December 2017
    This is the PERFECT Family retreat! Each year, my husband and I take our 5 grown kids and their significant others to the Keys for a family vacation. We've tried multiple...
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    About this property
    Oceanfront 6 bed/4 bath home with panoramic ocean view on Cudjoe Key. Sleeps 12+. Beach, Hot Tub, Floating Dock, Heated Pool, Kayaks and 540 square foot screened in porch overlooking the Atlantic ocean. This house has been very popular with large groups. New memory foam mattresses in 2018....
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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    Canal Front Home with Seawall & Kayaks1 / 18
    (1)Excellent
    Little Torch Key
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2018
    Perfect location to Picnic Island, absolutely could not ask for more for a little house to offer. Slept 7 of us very comfortably, Amy with Walkabout Retreats is a super host...
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    About this property
    This home is located in a quiet community on a deep canal with great boating access to open water. 2 kayaks and 2 bikes are included with your rental. Heated swimming pool and Tiki Hut for relaxing in the shade. Just a short 30 minute drive to Key West. Kiki's Sand Bar and Grill is a great place...
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    33042, Little Torch Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Concrete home with canal front view. 80 foot concrete dock with easy access to the Gulf and Ocean. Lots of parking on the oversized lot . 3 screened in porches for outdoor entertaining. The home is well stocked with everything you’ll need to enjoy your stay. This is a 28 day minimum rental....
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Little Torch Key
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Waterfront
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Lower Keys 6BR/4.5 getaway has a private boat basin and ramp, a pool, and a separate guest house with its own kitchen and living room. Relax in your outdoor oasis at the water's edge before heading out to scuba dive, shop, fish, or even embark on a lobstering adventure. Located on Pine...
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    Location Information
    33042, Little Torch Key, Lower Keys
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental is 28 Days to a single family or party (no subleases allowed). Special 11% off Sept - mid Dec 2018 rates on availabile dates.$143/night. All pictures are post IRMA.Simply Breathtaking VIEWS of the sunset over the ocean like this right from this home and from the deck. 2 Bedroom 2...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront Home Rental in Ramrod Key, Florida1 / 12
    (5)Very good
    Ramrod Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Patio
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3bd/2ba home w/ sliding glass doors off entire back of house provides never ending views of the Atlantic Ocean Fully equipped home just 25 min from Key West, 10 minutes from beautiful Bahia Honda State Park. Deep water access w/ mean draft of 3ft. Ramrod Key features Looe key reef for excellent...
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    33042, Ramrod Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Little Torch Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the balmy breezes at Island Chalet for a laid back Florida Keys vacation. Located on Little Torch Key with awesome boat access to Big Pine channel. Just a few minutes away to Dolphin Marina for all the boating necessities for those fun fishing trips. Enjoy the chalet-style feeling of the...
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    Location Information
    33042, Little Torch Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    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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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Paradise Oceanfront Home with Pool1 / 25
    (10)Excellent
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2017
    Our family of four loved everything about this property - the location, the kayaks and bikes that are provided, Cudjoe Bay (which is just steps from the deck), the view! So...
    Reviewed 19 July 2016
    I had originally reserved a larger house a few streets down from this one. That was when there was going to be a much larger group. However, due to the fact that some friends...
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    About this property
    Paradise found, this house has it all, beach, dipping pool, screened in porch, kayaks, bikes, floating dock and amazing views. This has been a popular honeymoon and anniversary celebration home for over 15 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise n Summerland Key Cove1 / 20
    (1)Excellent
    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2016
    Whatever I'd hoped for, this vacation home has without question, surpassed any and all expectations! Excellent location; in a quiet and beautiful strip. Loved relaxing on the...
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    About this property
    Amazing canal front 3 bed 2 bath open concept house located in prestigious community of Summerland Key Cove. It is the first canal from open water and one of just a few flow-through canals providing excellent water quality. The canal is deep and wide. Expect to see lobsters, crabs and other sea...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    florida keys vacation rental1 / 13
    (1)Excellent
    Little Torch Key
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2018
    This property is wonderful and the pictures do not do it justice. Very clean & the houses comes with everything you need. The pool is huge and plenty of room for our large...
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    About this property
    Beautiful 2-Acre Waterfront property, Main House sleeps 6, possibly 8, and sits very close to the water. You can watch the sun come up across the channel from your bed, or slip outside and and watch from the tiki hut, or take a few more steps and settle into one of the hammocks, or a few more steps...
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    33042, Little Torch Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy Paradise in the comfortable island style of Catch of the Day! This 2 bedroom 2 bath canal front home on Cudjoe offers the casual lifestyle of the Lower Keys. It features all amenities including new furnishings, a well appointed kitchen and fresh linens. A large under-house storage area...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ramrod Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy all the best the Keys have to offer at this super special Little Torch vacation rental home. All updated with beautiful tropical colors and furnishings with attention to every detail. The large living/ dining area with full seating for 6 so all your friends and guest can enjoy those special...
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    33042, Ramrod Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Island Living1 / 15
    (2)Very good
    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Washer
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2015
    Island Living is quite comfortable for us. Plenty of room for friends. Quiet, safe neighborhood. Easy ride to shopping and Key West. The pool is very nice. Boating access is...
    Reviewed 2 April 2012
    The home and pool were clean, comfortable and nicely furnished. Kitchen is simply furnished and could use a variety of serving dishes and sharp knives. You will need to purchase...
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    About this property
    Lovely three Bedroom/2 Bath home with pool and hot tub located on Summerland Key. Mile marker 25. Deep water swimming canal with boat ramp and dockage. Large screened in porch for outdoor dining and BBQ grill. Tropical landscape and extra sleeping. Sleeps up to 8. 28 day rental. Please...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Blue Palms Retreat (formerly known as Heron's Roost)1 / 24
    (2)Excellent
    Cudjoe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2018
    The house was clean, up to date, and very comfortable. The furniture under the house was great, as we could sip on cold drinks in the shade and still have a view of the ocean...
    Reviewed 23 August 2018
    We so enjoyed staying at Blue Palms Retreat. The views from the house were simply breathtaking. We enjoyed lounging by the pool and hanging out in the gazaebo. Fishing was...
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    About this property
    This house is a charmer. 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key. Large, heated swimming pool with shaded hang out area and ping pong table. Double kayak and hammock provided. Bikes and paddle boards available for rent. Charming character with hand made pottery...
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    Location Information
    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ramrod Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2Bd/2Ba Home With Sleeper Sofa Can Sleep Up To 6 People Very comfortable elegant 2-bed 2-bath, two story stilt home with a wraparound deck in a tropical paradise in the Lower Keys. Decorated in a tasteful nautical decor with very large open and spacious tiled living area, this house offers many...
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    33042, Ramrod Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ramrod Key
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bahia Azul, 'Bay of Blue' is exactly the perfect spot for your next Florida Keys adventure. The open water views are just stunning and spectacular. Its location at the end of the street makes this a very private get-away. This large home will accommodate all your friends and family with 4 bedrooms...
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    33042, Ramrod Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 2 Kayaks and padl board1 / 12
    (1)Excellent
    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • DVD Player
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 November 2018
    What an awesome place to stay. Home had everything we needed in the kitchen to cook a Thanksgiving meal for two. All we needed was to stop at Winn Dixie in Big Pine and we were...
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    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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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sugarloaf
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW Situated on 475 feet of lush canal frontage, this gated 3BR/2BA provides a luxurious getaway with panoramic views of Sugarloaf Sound. Highlights of the property include prime outdoor entertaining space and a spacious floor plan furnished in a beachy style. Your backyard oasis...
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    33042, Sugarloaf, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Little Torch Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Pack your floral shirts, swimming gear and sandals and come on down to Angelfish Cove. Fun is the order of the day. Enjoy the beautiful crystal clear swimming pool or jump in your boat to go explore some of the best fishing and diving the Florida Keys has to offer. This home offers 70 feet of canal...
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    33043, Little Torch Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cudjoe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Summerland Key
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedroom / 2 Bath Upstairs 1 King Bed, 2 Queen Spacious office with open water views 2 Bedroom/ 1 Bath Down 1 King, 2 twin 2 Separate living room areas, up and down, each with large flat screen TV's and DVD players Large screened porch up and down Heated Pool w/ outdoor shower and pergola...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sugarloaf
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Sugarloaf Key is one of the most desirable islands in the Lower Keys. Large roomy lots, plenty of biking and walking trails in the area. Kayaking , boating and diving are just some of the water sports you will enjoy during your stay. Green Turtle Landing is just the right spot to spend your Florida...
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    33042, Sugarloaf, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Barry Beach (weekly Rental)1 / 15
    (1)Excellent
    Little Torch Key
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Waterfront
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2016
    We traveled to Little Torch Key with another family for the first time and stayed at Barry Beach. This rental was PERFECT! The house is bigger than it appears in the photos and...
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    About this property
    This Florida Style home was built in 1965 and wonderful surprises await you on the inside. The ground level house is painted in bright tropical colors to give you that that old island feel. This spacious 2,000 square foot house has plenty of room to spread out. On one side are 2 king size master...
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    Location Information
    33042, Little Torch Key, Lower Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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