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Matecumbe Key Pet Friendly Holiday Rentals

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    Travellers to Matecumbe Key are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    70 Matching Rentals in the Matecumbe Key AreaView all 311 rentals
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    75130 Overseas Highway1 / 19
    (5)Excellent
    Matecumbe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Matecumbe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 10 kilometres of Matecumbe Key.
    **Fall Promo** Amazing views from this Oceanside Home near Pennekamp, dining and1 / 25
    (3)Very good
    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Fabulous 6/4 Tropical Waterfront Pool Home!1 / 27
    (1)Excellent
    Islamorada
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    We are one of two couples who each have rented a level for the past six winter seasons and we are so looking forward to returning in 2018. The location is perfect-within one...
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    About this property
    Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. Video of house and area available upon request. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. Our beautiful home is Great...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    Islamorada Tropical Canalfront Paradise1 / 13
    (1)Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Parking
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2018
    Wow! This property is just perfect for a quick getaway! The backyard was so fun, for our entire family. My kids loved the hot tub, my wife loved the waterfront view and I loved...
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    About this property
    The moment you step in the back yard, you'll know vacation has begun. . . time stands still as the laid-back island lifestyle takes over...Totally remodeled, canal-front home, quiet and in the nicest of neighborhoods (Plantation Key Colony). The 2 bed/2 bath stilted (upper unit) island retreat is...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Comfortable Clean HouseBoat in an amazing location1 / 25
    (4)Excellent
    Tavernier
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2016
    What's not to love? Heidi greeted us with warmth and a smile. She showed us around and provided recommendations for great dinner and SCUBA spots. The house boat was spotless, it...
    Reviewed 3 August 2016
    This is a great little houseboat, clean and comfortable. The owner is kind and responsive. I would highly recommend. There is a little bar and grill at the marina, it closes at...
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    About this property
    Very spacious Houseboat. One bedroom with queen size bed. Very comfortable queen size pull out sleeper sofa, and extendable single sleeper Large closet and lots of storage space. Full bathroom, shower and bath towels, hand towels and washcloths. A fully equipped galley with all the comforts of...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    Beautiful Bayside View1 / 39
    (1)Excellent
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 May 2018
    My family just LOVED this house. The backyard is amazing with a beautiful view and plenty of space for boat-dockage. My family had fun paddle boarding, kayaking, and...
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    About this property
    Bayside View is truly an amazing Florida Keys home, with great Bay views from all floors! Bayside View is a 3 bedroom/3 bath home that is directly on the Florida Bay. This location satisfies all of your fishing & water sport desires. The home is completely renovated and absolutely gorgeous. The...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Islamorada
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Prestigious Venetian Shores subdivision in Islamorada! This vacation home has 5 bedrooms and 3 bathrooms with 100'  concrete dock. The house is situated into two separate living quarters. Upstairs is a large master suite and 2 guest bedrooms, cathedral ceilings & fully stocked, eat-in kitchen,...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (4)Very good
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2018
    I was having trouble booking my reservation online (technicality), and had to call in for help. One of the girls there was able to help me quickly, booked me & took my payment...
    Reviewed 19 January 2018
    Yes there was..DO NOT RENT FROM ITRIP/PHOENIX RENTALS.They were totally dishonest with me. They did not tell me that there was major construction going on in the building I...
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    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
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    Islamorada, Florida Keys FL 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Tavernier family vacation home is like 'home away from home'. Property is fenced. Nicely decorated and tiled throughout our home is very well kept and clean only four homes from open Bay access with clear water canal and direct ocean access via Tavernier Creek. Master suite features queen size...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    **Summer Promo** Ocean Front Keys Home with Private Beach - Great for Kite Surfi1 / 25
    (2)Average
    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Had a wonderful time beach just out front and did a lot "beaching". Close to a nice supermarket and rental places. Will definitely be back! Thanks for a great get away!
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Beautiful four bedroom, Ocean Front home with...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Islamorada
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful Venetian Shores home... It truly is a must see! The interior is clean and nicely decorated. The large porch on the back allows you to see the famous Florida Keys sunsets from your own home! Located a few houses down from Snake Creek, you'll have quick ocean and bay access. Deep...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer and living area that opens up onto a large...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage....
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    MATECUMBE JEWEL1 / 25
    (2)Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Private Outdoor Pool (Heated)
    • Grill
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 December 2017
    Very accommodating, house is well taken care of and lots of amenities. Just need to figure out how to stay longer.
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    About this property
    ***FALL SPECIAL*** RECEIVE 10% OFF RENT FOR ALL BOOKINGS IN SEPTEMBER AND OCTOBER. Minimum Rental: 28 Days 'Matecumbe Jewel' is a jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in the beachside pool. The front home sits...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Islamorada
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Deam home in they keys is one of the very few legal weekly rentals in Islamorada. It is a 4000 square foot home on water with heated Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Islamorada
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Gated Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding Staircase, Expansive Ocean Views, Over 4000 Sq. Ft. of Living Space. Heated Pool, Sandy Back Yard, Gated Entrance Lined With Palm Trees. Enjoy the Ocean Views and...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Patio
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2013
    We have rented the upper duplex of Little Bay in April for the last few years. it is a beautiful property in a perfect setting. The grounds are kept immaculately and the area...
    Reviewed 5 November 2012
    We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach...
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    About this property
    Minimum Rental: 7 Days Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Incredible Luxury Home with Waterfront!! Paradise1 / 17
    (2)Excellent
    Islamorada
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Grill
    • Washer
    • Hot Tub
    • Balcony
    • Central Heating
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 December 2017
    Cannot even express in words how great of an experience my family had! The house is unbelievable, with two apartments downstairs and three bedrooms upstairs. The yard is amazing...
    Reviewed 5 December 2017
    I loved having everyone at one location and with the 3 separate living areas, there was plenty of space! Easy access to a great bike/walking path. Great restaurants just a...
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    About this property
    Lo-Key Estate is truly a luxury Keys home situated on a private 400’ waterfront peninsula with the use of a tropical swimming pool w/waterfall and hot tub(shared w/guest house) There are Ocean Views from the 2 & 3rd floors. Lo-Key is a custom 5 bedroom/5 bath home that opens onto Florida Bay...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    LITTLE BAY - Lower Duplex1 / 23
    (4)Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 7 Days Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is the Perfect getaway for large groups!  You can rent from 1 to 4 homes depending on the size of your group. The Pelican and Egret homes will offer you 2 homes, 5 bedrooms, and one pool.  The Pelican is a 3 bedroom 2 bath ocean front pool home which will sleep up to 8 people.  (Sofa...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    San Roc is a private home with 150 feet of oceanfront and spectacular views of open water with heated pool and spa. Beautiful 4 Bedroom 3 Bath Home situated on over 2.5 acre secluded wooded lot. Landscaped grounds in a premier area of Islamorada, Florida known as 'Millionaires Row' Enjoy...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Grill
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***FALL SPECIAL*** RECEIVE 10% OFF RENT FOR ALL BOOKINGS IN SEPTEMBER, OCTOBER AND NOVEMBER. MINIMUM STAY: 28 DAYS 'Flamingo Cottage' is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tavernier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Hot Tub
    • Terrace
    • Grill
    • Parking
    • Cable/satellite TV
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'Bay Therapy' invites happy vacationing. Owners call their special getaway 'Bay Therapy' for many reasons. It is located in a great neighborhood in Key Largo. It is convenient to the mainland and is the gateway to the Keys. Since purchasing this home the owners have...
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    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    VILLA RIOLO1 / 25
    (2)Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2018
    We have stayed in many places, this is one of our favorites by far. Great location, great fishing. Very clean and well kept. Has a private boat ramp which was very important...
    Reviewed 13 August 2014
    Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.
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    About this property
    ***FALL SPECIAL*** RECEIVE 10% OFF RENT FOR ALL BOOKINGS IN OCTOBER AND NOVEMBER. Minimum Rental: 28 Days 'Villa Riolo' is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key's Villa1 / 54
    (1)Excellent
    Tavernier
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Secure Parking
    • Private Garden
    • Children's Pool
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Rolando was amazing. We were planning a small intimate wedding with less than 15 people. He was sooooo helpful and wonderful. We arrived on 14th to a clean home. Rolando was...
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    About this property
    This is a very spacious 2,352 sf canal front house accommodating up to 12 guess. It is fully furnish with all brand new high end furniture. The house is located on the ocean side in Downtown Key Largo on MM 100. It’s 5-15 minutes away from all the restaurants, bars and cafes. It is also 5-15...
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    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    SUNSHINE PLACE1 / 23
    (12)Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Grill
    • Internet Access
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    We loved this condo in a beautiful location with excellent amenities. Spotlessly clean and very comfortable.
    Reviewed 22 August 2018
    Beautiful property! A piece of paradise in Islamorada. Great service from the Keys Holidays Rentals team. We will come back to this piece of heaven.
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    About this property
    Minimum Rental: 7 Days 'Sunshine Place' is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Waterfront
    • Hot Tub
    • Terrace
    • Washer
    • Ocean Views
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Endless open water views with spectacular sunrises and sunset colored skies await in this private gated estate. Sink your toes into the natural sand beach. Enjoy your privacy at the heated pool and spa among lush tropical vegetation and palm trees. This Key West styled house offers stunning...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***FALL SPECIAL*** RECEIVE 20% OFF RENT FOR ALL BOOKINGS IN OCTOBER AND NOVEMBER. Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms....
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps eight people. Master bedroom has a king bed with access to the balcony. Second bedroom has a queen bed and third one has two twin beds. TVs in every...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental1 / 38
    (28)Excellent
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    Over the years, we have stayed here 4 times, and each time gets better due to the improvements to the property. The location is perfect and relaxing for folks who like to fish...
    Reviewed 28 March 2016
    This is my fourth year at the property and it has only gotten better. There were some criticism of the deck conditions and lack of refrigerator at the outside Tiki hut. Those...
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    About this property
    Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email me for the application. Weekly vacation rental...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    LYONS LANDING1 / 24
    (2)Excellent
    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Patio
    • Terrace
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 February 2018
    Had a great time.we hope to do it again.we caught many fish from the dock.my family had a ball.they let us bring our small dog.
    Reviewed 27 June 2017
    Every room is comfortable,charming and the property managed to make you feel comfortable and at home..with every amenity..including an ice maker..so nice to have here in The...
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    About this property
    Minimum Rental: 28 Days 'Lyons Landing' is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home. 3 bedrooms and two baths on the upper level plus a bedroom and...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Islamorada
    5 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people. The Upper Duplex &...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 18
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    Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Grill
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Tavernier
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Terrace
    • Washer
    • DVD Player
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous waterfront home is a fisherman's dream with 65' of concrete dock, a covered fish cleaning station WITH a commercial ice machine, running water & outdoor shower - backyard shaded by palm trees. Located at MM90 oceanside right off Tavernier Creek with easy, quick ocean & bay access -...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Tavernier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Balcony
    • Terrace
    • Parking
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'Palm Harbor' is a spacious elegant home with pool and dock. Gently swaying palm trees greet you at the gated entrance to this wonderful home. The ground level entry features a billiard/game room, bedroom and full bath. An open curved staircase leads to the 2nd floor...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Cable/satellite TV
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Infinite ocean views from the large windows at this modern and luxurious oceanfront condo at mile marker 87. Accommodation - Sleeps 4 Master Bedroom: - King Size Bed - Night Stands - Reading Lamps - Dresser with Drawers...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Waterfront Home In Florida Keys1 / 22
    (3)Very good
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Patio
    • Washer
    • Internet Access
    • Balcony
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relaxing Home in the Florida Keys. Come enjoy a view from all but 1 room in this 2 Bedroom 2 Bath home. New 12,000lb boat lift to keep your boat on up and out of the water. 2 Balconys to relax and enjoy the views. Plentiful parking for car, truck, Motorhome, boat trailer. This home is 2nd key in...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Islamorada
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    CONCH BAR SOUTH1 / 24
    (2)Very good
    Tavernier
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
    • Grill
    • Patio
    • Terrace
    • Parking
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2018
    The service from start to finish was outstanding! Everyone was so helpful and responsive to every need. We even received a welcome basket.
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    ***FALL SPECIAL*** RECEIVE 20% OFF RENT FOR ALL BOOKINGS IN SEPTEMBER, OCTOBER AND NOVEMBER. Minimum Rental: 28 Days 'Conch Bar South' is a magnificent home is located at the mouth of a wide canal in Plantation Key and offers phenomenal open water views. The furnishings are new and provide a...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beautiful Oceanfront, heated pool, free wifi1 / 27
    (19)Excellent
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Oceanfront splendor on the Atlantic ocean has a weekly vacation rental license, which allows for weekly rentals. There is a 350' pier that you can fish off of or simply jump in the ocean. The dock can accommodate most size boats if you wish to bring one. Just relax by the pool on those...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Upper Duplex is a 1,500 sq ft unit with 2 bedrooms, 2 full...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    MANATEE MANOR1 / 25
    (2)Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Internet Access
    • Patio
    • Parking
    • Grill
    • Private Outdoor Pool (Heated)
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2017
    We enjoyed the month of June at Manatee Manor. You are greeted on the first floor with a comfortable game room area that includes a pool table that converts to ping pong and...
    Reviewed 10 August 2017
    Our family stayed and Manatee Manor for the month of July and had the perfect summer vacation. The layout of the home as well as the quality of the furnishings, location and...
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    About this property
    ***FALL SPECIAL*** RECEIVE 10% OFF RENT FOR ALL BOOKINGS IN SEPTEMBER, OCTOBER AND NOVEMBER. Minimum Rental: 28 Days 'Manatee Manor' is a 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay. Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget all the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    BLUE WATER RETREAT1 / 26
    (3)Very good
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Patio
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2017
    We recently returned from a month long vacation stay at Blue Water Retreat and it was so hard to leave! This house is situated on an ocean canal with spectacular ocean views...
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    About this property
    Minimum Rental: 28 Days 'Blue Water Retreat' is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you have your sights set on the ideal spot to spend your next tropical getaway, then jump on the chance to book your stay at this dog-friendly, oceanfront Islamorada home on a one-acre lot. Boasting a private stretch of white sand beach, a private pool, hot tub, and water toys like kayaks and...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get ready to enjoy your Islamorada Vacation in this beautiful deep water canal home! Located at Mile Marker 90 in Plantation Key Colony, this 3 bedroom, 3 bath home has it all. Upstairs has 2 bedrooms, two baths, beautiful open kitchen and family room, large screened porch, washer and dryer. Your...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Lower Duplex is a 1,500 sq ft unit with 2 bedrooms, 2 full...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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