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Sugarloaf Key Holiday Rentals

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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 88 Rentals in Sugarloaf Key
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    Sugarloaf Key
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Sugarloaf Key
    5 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    Sugarloaf Key
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Quaint romantic cottage with street parking, close to the beach & adventure!1 / 24
    (49)Very good
    Sugarloaf Key
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 January 2016
    My 8 friends and I stayed here this last week and had a great time. It's directly off duval and has three king beds with a pullout couch. The beds were very comfortable while...
    Reviewed 2 December 2015
    Right in the heart of Duval and nicely tucked away from the street. Rental was very clean and orderly however it did have a strong musty smell so we purchased multiple air...
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    About this property
    Hemingway's Shadow *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.* Whisk your special someone away for a tranquil retreat when you book your next vacation at this Key West cottage. Putting you...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sugarloaf Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Parking
    • Terrace
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Affectionately known as the Captain’s Quarters, this two-story custom-built 3BR/3BA is located on a quiet lane in Bahama Village. This lovely neighborhood exudes a charming old Key West vibe. Please inquire for options. Step out to your back yard for a dip in the private pool, set amid lush...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The following rentals are within 15 kilometres of Sugarloaf Key.
    Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort1 / 11
    (1)Very good
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • Waterfront
    • Grill
    • Washer
    • Central Heating
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Ocean view, on a canal, three lots from open water in Venture Out Resort; a safe, gated community. Park your boat or kayak right outside your front door on the canal, or just relax and enjoy your mosaic picnic table and 4 patio chairs, and Weber charcoal BBQ. Only 7 steps up or down to...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
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    Suitability
    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Little Torch Key
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Little Torch Retreat *Please note that this home only allows minimum stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Enjoy the amazing water views from this cozy home situated in a quiet, family-friendly neighborhood. This fisherman's paradise is...
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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Blue weekly vacation rental, great view. Heated private Pool.1 / 25
    (1)Excellent
    Summerland Key
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation home sits behind some mangroves and has a view over Cudjoe Bay to the Atlantic. 4 bedroom and 2 bathrooms. Large deck with water access for a small boat. Water access has a shallow area to and from the deep area the boat would be docked at. Vacation home sits far off of the main road for a...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Little Torch Key
    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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    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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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cudjoe Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the breathtaking open water views from the multi-level porches of Waterside Bay! This 3 story custom home has 3 bedroom and 3 baths and has upscale yet comfortable living. Complete with a Gourmet Kitchen of stainless steel appliances and granite counters making entertaining a breeze....
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Waterfront Cozy Camper with Boat Ramp & Dock!1 / 19
    (1)Excellent
    Little Torch Key
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Grill
    • Washer
    • Waterfront
    • Ocean Views
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2018
    Great dock for your boat. Camper is not fancy but it is very very clean and well stocked. Plenty of towels even beach towels. Fully stock kitchen right now to salt and pepper...
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    About this property
    Welcome to paradise! Come experience the amazing Keys and beautiful open water home with ramp and long boat 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 5
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    Cudjoe Key
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Secure Parking
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    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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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Terrace
    • Grill
    • Washer
    • Waterfront
    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ramrod Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a WEEKLY RENTAL! Welcome to Sunset Bay, where you’ll experience the most glorious sunsets! Located on tranquil Big Torch Key, Sunset Bay is situated on the open water of Niles Channel, Gulf side. This home is an outdoor lover’s delight! Situated on a large parcel with a long grassy...
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    Ramrod Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Little Torch Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Patio
    • 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 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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    Family Retreat ocean front home with private pool1 / 25
    (16)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 1 May 2019
    Our 3 generation family of 7 stayed at Family Retreat in April 2019. The house is perfect for the 2 married couples, 1 single person, and 2 teenage boys. We used 5 of the 6...
    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.
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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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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    Oceanview Estate 15 minutes from Key West - 6 bedroom accommodate 13 guests1 / 56
    (49)Very good
    Cudjoe Key
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Patio
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 January 2017
    This house was perfect for our large family to stay. We used the whole property and Kazi was great to work with. We had perfect weather and we had a great time in the pool...
    Reviewed 14 January 2017
    Kris and Adam both of our fabulous host were fantastic! When we arrived Kris was there to welcome us and made our check-in easy, answered any questions and any issues right away...
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    About this property
    We are away from the hustle of Key West activities, but close enough to the excitement when you want it and the Atlantic Ocean’s spectacular sunrises, sunsets and endless views of the starry nights. We have one of a kind property in the Florida Keys with custom built fence, gated, quiet and...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    Serene Barry Cove Top Tier with Boat Parking & Heated Pool!1 / 31
    (1)Very good
    Little Torch Key
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Washer
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    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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    Charming 3bedroom/2bath home in the Florida Keys1 / 21
    (3)Very good
    Cudjoe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Waterfront
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 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...
    Reviewed 20 October 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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    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...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fandango1 / 30
    (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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    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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    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    Suitability
    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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    Little Torch Key
    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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    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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    Sugarloaf, Florida Keys 33042
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    Summerland Key
    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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    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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    Location Information
    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Location Information
    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Oksana's Tropical Beach Oasis1 / 34
    (2)Excellent
    Cudjoe Key
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Garden
    • Air Conditioning
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    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2017
    The house is very nice. They are upgrading many of the rooms...the kitchen is really nice. The view is spectacular and the large backyard is great. The fact that they allow...
    Reviewed 1 May 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...
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    About this property
    Oksana's Oasis is a spacious ocean front property with spectacular views and a large swimming pool with 10 foot overflow spa. Kayaking is great in the shallow waters of the Keys and this rental provides 2 double and 2 single kayaks. There is a long pier that goes out over the shallow water and...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    Cudjoe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful house nestled far off of US 1. Rent one or both of our other properties that are within feet of each other for a great full family vacation. Nice water view over Cudjoe Bay, comes with water access for a small boat with options to dock larger and multiple boats nearby at no extra cost....
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sugarloaf
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1,700 sq ft house is located on Lower Sugarloaf Shores at Mile Marker 17, a half mile off of US 1 in an extremely quiet neighborhood. It is a three bedroom, three bath elevated house. All of the bedrooms are located on the second floor with two full bathrooms. Each bedroom has a queen size...
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    Sugarloaf, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Little Torch Key
    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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    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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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Ramrod Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Private Garden
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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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    Ramrod Key, Florida Keys 33042
    Holiday Rental House - 2 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
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    Smoking allowed
    About this property
    This great Vacation Home is conveniently located on Cudjoe Key. The all tile kitchen is fully equipped and living & dining rooms provide ideal entertaining areas for friends and family. Enjoy warm, tropical breezes on the large wood dock, overlooking the deepwater canal, perfect for swimming and...
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    Cudjoe Key, Florida Keys 33042
    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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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Coral House is a prime destination spot for a great Florida Keys vacation! Conveniently located on Ramrod Key, mile marker 27. Close to all the choice restaurants and services that the Florida Keys have to offer. This home is beautifully decorated in island style with attention to even the...
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    Ramrod Key, Florida Keys 33042
    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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    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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    Location Information
    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ramrod Retreat1 / 10
    (1)Terrible
    Ramrod 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
    This Ramrod Key rental is a great spot for your next Florida Keys vacation. Comfortable and affordable, with 2 bedrooms downstairs and 1 bedroom upstairs. This home has two bathrooms, ample size kitchen and living areas, and the screened porch overlooks a peaceful canal with 28ft of dock space for...
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    Ramrod Key, Florida Keys 33042
    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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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Little Torch Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Patio
    • Grill
    • Waterfront
    • Washer
    Suitability
    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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    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lafitte Landing is the perfect destination for your Florida Keys vacation. Very nicely appointed 2 bedroom, 2 bathroom canal front home is very comfortable and spacious. This home offers a living-dining-kitchen great room floor plan with comfortable seating and a flat screen TV. Double sliding...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Cudjoe Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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
    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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    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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    Little Torch Key, Lower Keys 33043
    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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    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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    Little Torch Key, Lower Keys 33043
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cudjoe Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kick back and relax in this Island vacation home. Or, enjoy the spacious deck located off the kitchen area, and take in the warm tropical breezes, canal and spectacular sunset skies. Fish from the dock or take advantage of the convenient boating access and cruise out to Looe Key, site of some of...
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    Cudjoe Key, Florida Keys 33042
    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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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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