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Pet Friendly Holiday Rentals in Matecumbe Key

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    Travellers to Matecumbe Key are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    74 Matching Rentals in the Matecumbe Key AreaView all 324 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.
    FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 31
    (5)Excellent
    Islamorada
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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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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    33070, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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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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    33036, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    **Winter Promo**  Amazing views from this Oceanside Home near Pennekamp, dining1 / 25
    (3)Very good
    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
    • Cable/satellite TV
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    • Grill
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2016
    Here is the bottom line..after about a week of our two month rental we had already rented this home for next year. The location is awesome and fishing off the dock was...
    Reviewed 25 March 2015
    Great House! Big enough for extended family. I really enjoyed the dock and the view of the water. Clean and neat.
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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 *** *** Owner is highly motivated to rent! Contact...
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    33070, Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Fabulous 6 Bedrooms /4 Bathrooms Tropical Waterfront Pool Home!1 / 15
    (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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    33070, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    33036, Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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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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    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    **Winter Promo**  Ocean Front Keys Home with Private Beach - Great for Kite Surf1 / 25
    (2)Average
    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Balcony
    • Grill
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    • 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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    33036, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Tavernier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise on mile marker 90, minutes from the Ocean or Bay. Relax and enjoy the coastal breeze and rustling palms in your own private oasis. Sure to become your favorite Keys home-away-from-home, this waterfront villa boasts elegance at every level with its spacious layout, modern decor...
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    33070, Tavernier, Key Largo
    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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    33036, Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful three bedroom, waterfront home with a private dock & pool in sunny Key Largo (MM 104). Welcome to your own Keys oasis! Kick back like a local and relax in your own Keys home. This split level house is located in Key Largo; the Sports Fishing Capital of the World. It is a private home...
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    33037, Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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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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    33070, Tavernier, Key Largo
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 5
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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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    FL 33036, Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise Beach Sandy Oceanfront1 / 46
    (1)Excellent
    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
    Reviewed 4 November 2018
    There was a group of nine of us (2 families...4 adults and 5 kids). We had an amazing time at the house ....the home was amazing (tons of space) and the pool was perfect...
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    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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    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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    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Do you ever dream vacationing in The Florida Keys? We are pretty sure if you do, this is the home you were thinking about. Located in the Heart of Key Largo, this beautiful 3 bedroom 3 bath home is close to shopping, dining, and of course, world class fishing and diving. Bring your boat, kayak,...
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    33037, Tavernier, Key Largo
    Condo/Apartment - 3 Bedrooms, 3 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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    • 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
    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 station, a screened lanai, inviting décor and comfortable accommodations. It is located...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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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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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 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
    33070, Tavernier, Key Largo
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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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
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    • Cable/satellite TV
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    • 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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 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
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    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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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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
    33070, Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    LYONS LANDING1 / 24
    (1)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 28 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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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
    33037, Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 2 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
    33070, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    SUNSHINE PLACE1 / 23
    (13)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 2 weeks ago
    We've been coming to the keys for about 10 years. This was the first time we brought our boat and rented a house. Andy and her team at Keys Holiday Rental were outstanding...
    Reviewed 10 October 2018
    We loved this condo in a beautiful location with excellent amenities. Spotlessly clean and very comfortable.
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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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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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
    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 studio type apartment with a private bath on the ground level. This home has a cozy cottage...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
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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
    33070, Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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 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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    MY PARADISE1 / 25
    (5)Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Balcony
    • Internet Access
    • Parking
    • Patio
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2018
    We fell in love with Sunset Drive the first time we stayed. My Paradise was our first choice but was already rented during the time we wanted, so we stayed elsewhere. The next...
    Reviewed 4 July 2018
    As a family - and GROWING - We have vacationed in the Keys for many years. We have stayed on the same street and in the same one or two houses and are booked for next year...
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    About this property
    Minimum Rental: 28 Days 'My Paradise' is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Grill
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 28 DAYS 'Sunrise on Sunset' is the ULTIMATE BEACH FRONT HOME. There are BREATH TAKING OCEAN VIEWS from almost every room in this house! Play in the sand, walk into the ocean or sit under the covered ground level area. This spacious 3BR/3BA single family home offers many ways...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    SANCTUARY IN PARADISE1 / 21
    (5)Excellent
    Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2017
    We booked Sanctuary in Paradise as there were three families (9 people) traveling together. It was perfect as each family had separate sleeping quarters. We were able to...
    Reviewed 23 October 2014
    My family/extended family stayed here in June 2012 for two weeks and it was beyond wonderful. The owner ALWAYS was quick to respond to emails even if it was to say "you're...
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    About this property
    WWW.SCHOONERHAMMOCK.COM This unique property offers : -master suite -apartment -cottage -3 full kitchens On Atlantic Ocean. Simple, sweet, and serene sanctuary. Please contact Andy Cancela 828 808 1693 We love The Lord and look forward to sharing our home with you.
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    Location Information
    33070, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Tavernier
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Manatee Manor! Find paradise at this newly remodeled 2,100 square foot 4BR/3BA vacation home, set on the canal in Key Largo. With spacious interiors, an expansive backyard, and indoor/outdoor kitchen and dining areas, there’s plenty of room for six people. Spend your days poolside...
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    Location Information
    33037, Tavernier, Key Largo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    About this property
    ***SPECIAL*** 20% DISCOUNT ON 2018 NOVEMBER/DECEMBER RENTAL. 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 comfortable and extremely...
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    Location Information
    33070, Tavernier, Key Largo
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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
    33070, Tavernier, Key Largo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Islamorada
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • 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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
    • Internet Access
    • Grill
    • Parking
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. Sliding doors open from the dining area into the sunroom overlooking the canal....
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    MANATEE MANOR1 / 25
    (2)Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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
    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 located on a deep and wide canal with easy access to the Bay or a short ride to Tavernier Creek...
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    Location Information
    33070, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    VILLA RIOLO1 / 22
    (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
    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 over the years and for the first time the owners are offering you an opportunity to...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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