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Holiday Homes in Lower Keys

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    Travellers to Lower Keys are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    All 41 Rentals in Lower Keys
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    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Blue weekly vacation rental, great view. Heated private Pool.1 / 25
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Ocean Views
    • Balcony
    • Cable/satellite TV
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    • Washer
    • Waterfront
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Captain's Quarters *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. This one-of-a-kind waterfront home features an amazing entertaining space with a full-service boat bar, a 68-foot boat dock, a...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Waterfront
    • Washer
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • 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 200 foot long dock for your boat. Exclusive heated pool to relax and enjoy the surrounding ocean view - just breath taking! The private lot is .81 acre with two other rentals and still very spacious. Stunning...
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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    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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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Patio
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    • 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 250 ft. dock for your boat. Consider it a must-see rustic outdoor environment with fishing traps on lot, very typical in the Keys! The private lot is .68 acre with one other rental and still very...
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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Serene Barry Cove Top Tier with Boat Parking & Heated Pool!1 / 31
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Washer
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    • Cable/satellite TV
    • Balcony
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    • Ocean Views
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2019
    We stay in the place was good, had everything. But we want to use the dock and the owner said that part is private, and people will use that apartment shortly. Never came people...
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    About this property
    Welcome to Paradise! Come experience the amazing Keys and beautifully serene top tier home for your next land/boating adventure! Relax and enjoy the majestic landscape and heated pool - just breath taking! The private lot is .81 acre with two other rentals and still very spacious. Boat parking on...
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    Little Torch Key, Lower Keys 33042
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Parking
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ”Gone Fishing” is exactly where you will be during your vacation time at this pristine home on Summerland Key, just 23 miles to Key west and 25 miles to Marathon. Relax and enjoy cocktails and snacks by the heated and chilled swimming pool after a great day exploring all the treasures the Florida...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    florida keys vacation rental1 / 13
    (1)Excellent
    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 31 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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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Patio
    • Cable/satellite TV
    • Ocean Views
    • Washer
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Paradise! Come experience the amazing Keys and beautifully serene low tier home for your next land/boating adventure! Relax and enjoy the majestic landscape and heated pool - just breath taking! The private lot is .81 acre with two other rentals and still very spacious. Boat parking on...
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    Little Torch Key, Lower Keys 33042
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the cleanest blue water flow-thru canals in the Keys! This comfortable home is clean and conveniently located at MM 24.5 on Summerland Key, near the beginning of a deep blue water canal. This elevated CBS home has concrete floors covered in ceramic tile and new carpet in the bedrooms....
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Oceanfront House1 / 51
    (1)Excellent
    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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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    • Terrace
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a newly remodeled four bedrooms multimillion-dollar elegant mansion. The house has its own private beach located in the heart of Summerland Key. It is the perfect Key for a vacation getaway. Summerland Key is an island in the lower Florida Keys about 20 miles east of Key West. The island...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Waterfront
    • Hot Tub
    • Washer
    • DVD Player
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    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Duck Key Vacation Rentals! Located on a private island in the Florida Keys, our Duplex is the perfect spot for your next vacation! Within walking distance, you’re only minutes away from many outdoor activities like fishing, diving, snorkeling, dolphin encounters, sailing, parasailing,...
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    Lower Keys, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As the day dawns over Pine Channel and the spectacular sunrise greets you each morning it will be hard to decide where to have your first cup of coffee, the screened in porch or perhaps the L shaped dock with your boat secured and ready for a day of fishing, diving/snorkeling or exploring the...
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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Ocean Views
    • Washer
    • Terrace
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom, 2 Full Bathroom; 864 Square ft.; Sleeps 6; Kitchen - 1 Full; Bedding includes 1 King bed, 2 Twin beds, 1 Sofa bed most comfortable for 2 children; Laundry is in Common area; Balcony, In-room safe. Located midway along the Florida Keys, Marathon is just before the famous Seven Mile...
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    Lower Keys, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Patio
    • Ocean Views
    • Waterfront
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    • 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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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    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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    Little Torch Key, Lower Keys 33043
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Luxury waterfront accommodations await for the whole group. This stately home has all the best of everything. The large great room has lots of seating. 42' Sony flat-screen, hi-def TV with surround sound makes you feel like you are right in the middle of the action. Kitchen is a chef's delight with...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water boat access for the avid angler and plenty of dockage for all the water toys. This stylish home is outfitted in Florida tropical style with cool and comfortable leather in the...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    This spacious, Caribbean-style vacation home comes equipped with its own private swimming pool and great deep-water canal. This beautiful home has three stories including a super play room off the pool area with a ping-pong table and a big screen TV for the kids. The 2nd floor accommodates a large...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well-equipped, custom kitchen. Spacious living and dining rooms provide ideal entertaining areas for friends and family....
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    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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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Buccaneer Boathouse! Pack your floral shirts, swimming gear and sandals and come on down to Little Torch Key in the beautiful Florida Keys. This lovely home is spacious with 2 bedrooms and 2 bathrooms. It offers a large open kitchen, dining and living area for everyone to hang-out and...
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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Enjoy many peaceful days and evenings at Cruikshank Isle, situated right on the tip of Cruikshank Island on Summerland Key where astounding sunsets and ocean vistas will be yours. The grounds are very shady and groomed with a nice Tiki hut at the waters edge. Plenty of dockage on the canal side and...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you'll find some of the best deep water boating in the Lower Keys! Just imagine yourself gazing out at these spectacular ocean vistas! The entire water-side of this home is glass. Views just go on forever......
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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    'Conch Out' on your tropical vacation at this spacious and comfortable 3 bedroom, 2 bathroom canalfront home on Big Pine Key. Relax on a swing under your private tiki hut, entertain in the large screened porch with your own built-in grill, or take advantage of the quick, excellent boating to either...
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    Little Torch Key, Lower Keys 33043
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    Little Torch Key, Lower Keys 33043
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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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    Little Torch Key, Lower Keys 33043
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
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    Smoking allowed
    About this property
    Come live the Salt Life at Salty Retreat! Stay at this luxury top of the Line tropical style home on Summerland Key. Located in a very popular subdivision on Lagoon Drive with deep boating access. This home is five stars the moment you pull into the paver circular driveway. Sitting on two lots...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This beautiful custom home located in Jolly Rodger subdivision on Little Torch Key has the best of everything. Just furnished in 2012 with the finest tropical decor, flat screen TV's, wireless internet and top of the line gourmet kitchen. The large living area is spacious and cheery with tall...
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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on a pristine canal-front lot, situated in Little Torch Key, this well-appointed home offers all the amenities you will need to enjoy the casual lifestyle of the Lower Keys. The lovely back yard area has a gas BBQ grill, a dining table with seating for six, a cocktail table with seating for...
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    Location Information
    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pirates Pointe1 / 18
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 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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    Location Information
    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 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
    You will be absolutely delighted to vacation at this remarkable luxury vacation home on Summerland Key. This multimillion dollar home has only the best to offer. The kitchen is a chef's dream with top of the line stainless appliances, cook top, built in ovens and gorgeous stone countertops. The...
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    Location Information
    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • 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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    Location Information
    Little Torch Key, Lower Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Balcony
    • Patio
    • Washer
    • DVD Player
    • 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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    Location Information
    Summerland Key, Lower Keys 33042
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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