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Holiday Rentals near Bud n' Mary's Sportfishing Marina

79851 Overseas Hwy, Oceanside, Islamorada, Florida 33036-3812
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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 70 Rentals in Islamorada
    75731 Overseas Highway1 / 32
    (13)Very good
    4.0 miles from Bud n' Mary's Sportfishing Marina
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    76004 Overseas Highway1 / 23
    (4)Excellent
    3.7 miles from Bud n' Mary's Sportfishing Marina
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    132 Columbus Drive1 / 18
    (16)Very good
    3.1 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    75130 Overseas Highway1 / 19
    (5)Excellent
    4.5 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2017
    We stayed here for a few days and it was amazing. The house is warm and cozy and has all the details you need when away from home. The beachfront is wonderful and can go...
    Reviewed 21 June 2016
    This two bedroom home was the perfect getaway for my husband and me. The cute sea-theme décor added to the cozy ambience. The living room/kitchen are flanked with a queen...
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    About this property
    Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs...
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    Matecumbe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 31
    (5)Excellent
    3.4 miles from Bud n' Mary's Sportfishing Marina
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Ocean Views
    • Patio
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2018
    Despite our rainy week in Islandmorada, Sean helded to make our vacation seemless! We had 10 people staying with us to help celebrate my husbands 50th birthday. The house had...
    Reviewed 13 July 2017
    The property manager was super helpful and walked us through the entire house showing us all the nooks and crannies. I must say I've never had someone take close to 45-an hr to...
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    About this property
    ***7 day minimum rental - notwithstanding anything in the rates page the MINIMUM rental is 7 days ****This custom built 5 bedroom house has been immaculately taken care of and has a proper size elevator and is fully wheel chair accessible. Enjoy your stay in Sereni-key looking out to an endless...
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    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    76300 Overseas Highway1 / 25
    (10)Very good
    3.4 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    Reviewed 31 July 2018
    Islamorada! Lower Matecumbe! Paradise! This older, ideally located, and well maintained property is a jewel. Since my dad first introduced me to Islamorada 45 years ago, I've...
    Reviewed 1 April 2016
    Three of us stayed for a week in March 2016. Unfortunately two more friends had to pull out due to illness, so we had a surplus of rooms. The house is not the most modern of...
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    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. Near the house is the small Anne's Beach. There are nature trails,...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE1 / 16
    (9)Excellent
    4.5 miles from Bud n' Mary's Sportfishing Marina
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Patio
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 February 2017
    If you want a piece of heaven on earth? Stay at Casa Rio Islamorada. This quiet, restful and scenic waterfront paradise is the place for fun, love and romance. This place is in...
    Reviewed 8 February 2016
    We recently stayed at Casa Rio in Islamorada Florida, what a beautiful place. The apartment is located on a quiet residential cul de sac in a lovely part of Islamorada. The...
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    About this property
    The storm has passed and CasaRio Islamorada is awaiting your visit. We have lowered our rates to encourage more tourists into the area. ***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY*** Please contact us for all of our rates! Please enter 28 days into your request...
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    Matecumbe Key, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Private Beachfront Paradise1 / 45
    (12)Very good
    0.8 miles from Bud n' Mary's Sportfishing Marina
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Sauna
    • Waterfront
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 November 2016
    The friends we haven't seen in over 25-years since high school, decided to reunite in Islamorada, FL. The moment we set foot on this property, we knew we were in for a great...
    Reviewed 24 August 2016
    We just got back from a week in this beautiful house. We traveled with extended family and 2 young children- everyone loved it. We did rent a boat to go snorkeling and fishing...
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    About this property
    Village of Islamorada VR-110 Beautiful two story home ......four bedroom three baths.....on your private white sandy Beachfront property with large pool facing the ocean. First floor is independent with a very large one bedroom, bar with wine cooler full bath, living, dinning and new kitchen....
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    Matecumbe Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    137 LeSerra Lane1 / 31
    (7)Very good
    3.3 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed 25 March 2015
    We had a terrific time at 137 Lessara this February. The wildlife (birds, fish, manatee) viewing was incredible, the weather great, and the house was fantastic- especially the...
    Reviewed 5 June 2014
    This house had more than enough of everything needed away from home.The decks on both floors were great for relaxing,visiting, grilling and tanning.Plenty of space our three...
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    About this property
    Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in  Lower Matecumbe (South part of Islamorada). This home is the second one in on a point  and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee  maker, toaster, and blender. There are...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Incredible Luxury Home with Waterfront!! Paradise1 / 17
    (2)Excellent
    4.9 miles from Bud n' Mary's Sportfishing Marina
    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
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    140 Atlantic Lane1 / 25
    (8)Very good
    3.3 miles from Bud n' Mary's Sportfishing Marina
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 January 2015
    We seven people (3 couples and one single) stayed here for one week. This big house is located right on the Atlantic Ocean, but it has no beech. It has a great wraparound porch...
    Reviewed 12 August 2014
    The home that we stayed at was incredible! The accommodations, the view, the boat dock space was all great. It was fast in and out to the Atlantic Ocean to be able to scuba...
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    About this property
    Amazing ocean views can be enjoyed from this beautiful stilt home with separate mother- in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4.8 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great deep dockage and quick access to bay and ocean!!! Beach & Bay Bungalow. This home has it all. New 65' 4k HD television and high speed wireless interntet included. All bedrooms have flat screen television. Spectacular long water views from inside and out of this secluded estate property!...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    82754 Overseas Highway1 / 29
    (4)Excellent
    2.9 miles from Bud n' Mary's Sportfishing Marina
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    We have been staying in the keys for 5 years in a row & this was the best rental property we found. We are 4 guys (over 50) who want to go fishing and relax and this property...
    Reviewed 9 May 2017
    Our family (three generations) wanted a place in Islamorada with 5 bedrooms. We rented the Osprey Bay Villa for a week and it was a perfect fit. The bay side location provided...
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    About this property
    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully...
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    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3.9 miles from Bud n' Mary's Sportfishing Marina
    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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Islamorada Waterfront Paradise 21 / 29
    (5)Very good
    4.5 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2016
    House was nice - except we did not feel comfortable - could not feel at ease - felt like we were being watched - paid a lot of money
    Reviewed 22 April 2015
    My husband and I just returned from Casa Rio. The home was clean and comfortable and quaint. The outdoor area was beautiful, charming and relaxing. We had access to bicycles...
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    About this property
    iF YOUR PLANS CALL FOR LESS THAN A MONTH, PLEASE CONTACT ME. i MAY BE ABLE TO HELP. ***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY*** Please contact us for all of our rates! For shorter stays...make sure you have a minimum of 28 days entered in your contact form!...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.0 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 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
    With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this...
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    Matecumbe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.2 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3.5 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    'The Beach Fixes Everything'. That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beautiful Bayside View1 / 39
    (1)Excellent
    4.4 miles from Bud n' Mary's Sportfishing Marina
    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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ocean-Front Caribbean Home.1 / 21
    (2)Excellent
    2.2 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Washer
    • Balcony
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 March 2018
    Very much enjoyed our stay. House was beautiful and clean, staff was friendly and helpful. My mother and I loved relaxing in the hot tub and my father and husband very much...
    Reviewed 24 April 2015
    Rolled out of bed early every day this week with my boys and family friends for my favorite commute: 50 yard walk to a private boat slip at the resort. We rented a boat...
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    About this property
    The Royal Palm, South - Ocean Front Home ( recent fraud. NEVER wire us money. Payment for reservations can only be done via the phone, not online or via wire) Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil with nothing compromised this luxurious Caribbean home...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4.7 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.7 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Patio
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise Beach Sandy Oceanfront1 / 46
    (1)Excellent
    3.9 miles from Bud n' Mary's Sportfishing Marina
    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 2 weeks ago
    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
    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4.1 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise! Built in 2012 and designed by well-known Miami architect to mirror the curved shoreline of the beach, this private custom contemporary beach home is a one of a kind, unique design with gated entry, large private beach, and gorgeous ocean views from every room. Built using ICF...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2.7 miles from Bud n' Mary's Sportfishing Marina
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    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 Cottage is a bright and airy 1,250 sq ft unit with a huge...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    BEACON REEF 3101 / 21
    (3)Excellent
    4.5 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • Cable/satellite TV
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Loved our stay in this beautiful condo! The view is spectacular! Condo is well stocked with all of your needs for a wonderful vacation in Islamorada!!! Highly recommend this...
    Reviewed 11 October 2018
    Can't say enough great things about our stay at Beacon Reef 310!! From the moment you walk into the condo we knew we loved it, The whole place had that bright tropical feel...
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    About this property
    Minimum Rental: 28 Days 'Beacon Reef 310' is located in one of the most desirable condominium complexes in the Upper Keys. Convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your own private balcony...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4.7 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.1 miles from Bud n' Mary's Sportfishing Marina
    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    PALMS 3091 / 25
    (2)Excellent
    3.3 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Parking
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2018
    Last year we spent 3 months in this location, and we enjoyed it so much we increased our stay to 4 months this year. Close to restaurants and marinas.
    Reviewed 17 August 2017
    Our three month stay was excellent. We enjoyed the location and close proximity to where we had our boat stored.
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    About this property
    Minimum Rental: 28 Days 'The Palms #309' is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    100' Private Beach Front Ocean Front Estate1 / 42
    (2)Excellent
    4.0 miles from Bud n' Mary's Sportfishing Marina
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2018
    INCREDIBLE HOME ON THE BEACH!This beachfront home offered more amenities than any other home we have rented for vacation. Complete game room as well as kayaks and paddle...
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    About this property
    Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of Islamorada, Florida. This home features a private beach, 5 bedrooms, 3 ½ baths, family room, living room, game rooms, pool and bar. This home can comfortably accommodate 10-12 people with room to spare....
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4.9 miles from Bud n' Mary's Sportfishing Marina
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    3.3 miles from Bud n' Mary's Sportfishing Marina
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.8 miles from Bud n' Mary's Sportfishing Marina
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    PALMS 3141 / 25
    (2)Excellent
    3.3 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2018
    Key Holiday Rentals are the best, they are there when you need them and are there to answer any questions you have .
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    About this property
    Minimum Rental: 28 Days 'The Palms #314' is a sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina. You'll be able to see cruise ships as they...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    LITTLE BAY - Cottage1 / 24
    (2)Excellent
    3.3 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 2016
    Stayed in the cottage, 5 of us in total. Gorgeous cottage inside and out, set on a fabulous site with beautiful trees, shrubs, birds, green grass, stone paths, lots of parking...
    Reviewed 28 May 2013
    The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough...
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    About this property
    Minimum Rental: 7 Days 'Little Bay's Cottage' is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    PALMS 2141 / 24
    (1)Excellent
    3.3 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2015
    We have always enjoyed the keys and love staying at the Palms of Islamorada. The units are big enough and the amenities are nice. Unit 214 was nice and clean. A big TV for me...
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    About this property
    Minimum Rental: 28 Days 'The Palms #214' is a gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    SUNSHINE PLACE1 / 23
    (12)Excellent
    3.3 miles from Bud n' Mary's Sportfishing Marina
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Grill
    • Internet Access
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2018
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    0.1 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #405' is a diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    LITTLE BAY - Lower Duplex1 / 23
    (4)Excellent
    3.3 miles from Bud n' Mary's Sportfishing Marina
    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
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.4 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Grill
    • Hot Tub
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. 'Beacon Reef 406' is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient to...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3.4 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. 'Beacon Reef 522' offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy with your choice to stay here....
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    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.7 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    BEACON REEF 2221 / 25
    (2)Excellent
    3.4 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2018
    We have so much enjoyed staying in this condo, Beacon Reef 222. The condo is very comfortable with a great kitchen and living area. The master bedroom is amazing with a large...
    Reviewed 13 July 2017
    Great location! The pool, tiki bar and dock are all top notch. The ocean views are amazing. All equals the perfect family vacation.
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    About this property
    Minimum Rental: 28 Days 'Beacon Reef 222' is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada....
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4.9 miles from Bud n' Mary's Sportfishing Marina
    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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    3.3 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Patio
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #402' is a beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony. Watch the fishing boats...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    CASA DORADO1 / 24
    (2)Excellent
    3.5 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2018
    This is the third time we have stayed at Casa Dorado. It is a beautiful home in an amazing location. If you like fishing, boating,diving, snorkling, and amazing sunsets this is...
    Reviewed 9 June 2017
    Beautiful home with great access to boat launch and dockage at the house. Very neat and clean and every amenity you could want. Had some AC problems that Keys Holiday Rentals...
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    About this property
    Minimum Rental: 28 Days 'Casa Dorado' is an exceptional privately owned single family home located directly on Florida Bay on Lower Matecumbe Key in Islamorada. The house is named after the owners' favorite species of fish, the Dolphinfish, also known as Dorado in Spanish speaking coastal...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1.4 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, stylish house located in the heart of Islamorada. 3 Bedrooms and 2 baths located right on the ocean with a heated pool, private beach and more! Enjoy the large master bedroom with master bath and shower. Situated at the end of a quiet street that is walking/biking/carting distance to...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    BEACON REEF 5011 / 25
    (1)Excellent
    3.4 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2018
    Key holiday rentals are the agents for this property and were excellent to deal with from booking to departure.The apartment is of a first class standard and spotlessly...
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    About this property
    Minimum Rental: 28 Days 'Beacon Reef 501' is an exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless steel...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    BLUE WATER RETREAT1 / 26
    (3)Very good
    3.5 miles from Bud n' Mary's Sportfishing Marina
    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    VILLA RIOLO1 / 22
    (2)Excellent
    3.1 miles from Bud n' Mary's Sportfishing Marina
    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
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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