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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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    All 82 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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    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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    75130 Overseas Highway1 / 19
    (6)Excellent
    4.5 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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 Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Full kitchen with Subzero appliances and Viking stove. Chiseled-rock flooring throughout. Wrap-around verandas. Seamless curved-glass corner windows. High open-beam ceilings. Located on The...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    76004 Overseas Highway1 / 35
    (5)Excellent
    3.7 miles from Bud n' Mary's Sportfishing Marina
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed 25 December 2018
    It was perfect- ideal location on the waterfront in Islamorada which is easily the best part of the Keys. Close to Robbie’s and Bud N Mary’s for all the activities....scuba...
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    About this property
    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees.  This home sits directly on the bay and has 2 bedroom 2 bath upstairs and has a 2 bedroom 1 bathroom apartment.  The home is located at mile marker 76.   Near...
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Oceanfront Oasis - Pinch me am I dreaming!!!1 / 44
    (5)Excellent
    3.4 miles from Bud n' Mary's Sportfishing Marina
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Cable/satellite TV
    • 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
    ***NOTWITHSTANDING ANYTHING IN THE RATES PAGE THE MINIMUM RENTAL PERIOD IS 7 DAYS*** For the ultimate Keys experience, little can compare to settling into a custom-built home boasting its own private beach. Crafted with pleasure in mind, this luxurious five-bedroom, four-and-a-half bath house...
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    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    132 Columbus Drive1 / 18
    (17)Very good
    3.1 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 31 March 2019
    132 Columbus Drive, Islamorada, FL is a beautifully remodeled place to stay right on the water. Great views from living room and both bedrooms. We spent most our time right...
    Reviewed 11 January 2014
    Location, location, location; this home was a great getaway, and beautifully landscaped (but not manicured) with older Australian pines, sea grape, palms and silver buttonwood...
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    About this property
    Beautifully renovated home sits right on the ocean. With panoramic ocean views from every room in the house, you'll never want to leave. This 2 bedroom, 2 bath home has a great back porch, large yard, and shaded carport/ sitting area. Located in Lower Matecumbe, this house is close to downtown...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Private Beachfront Paradise1 / 45
    (14)Very good
    0.8 miles from Bud n' Mary's Sportfishing Marina
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Sauna
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 February 2020
    We had a wonderful stay! There house was newly renovated and remodeled and is beautiful. The pics here on this listing are out dated and it's gorgeous inside. Super cool the...
    Reviewed 30 October 2019
    What an amazing family vacation with the perfect place to stay. This home had everything we needed for both adults and kids. The view is spectacular and you aren't far from...
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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
    Incredible Luxury Home with Waterfront!! Paradise1 / 19
    (2)Excellent
    4.9 miles from Bud n' Mary's Sportfishing Marina
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Hot Tub
    • DVD Player
    • Air Conditioning
    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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    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    137 LeSerra Lane1 / 32
    (8)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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    Smoking allowed
    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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
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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
    3.8 miles from Bud n' Mary's Sportfishing Marina
    7 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Patio
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There is luxury, luxury and unrivaled, and then there is the Bayfront Chateau that offers that and more. Situated on more than seven acres of peerless Islamorada shorefront, this unique property reveals the very best in tropical vacations. The property only recently became available after decades...
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    Layton, Long Key
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 16
    140 Atlantic Lane1 / 49
    (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
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    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
    You'll fall in love with this little piece of paradise. Amazing ocean views can be enjoyed from every room in this beautiful home and separate guest quarters. With an open concept living, kitchen and dining room, a large wrap around porch, 5 bedrooms and 4 bathrooms, this house has everything you...
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    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    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
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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
    Paradise Beach Sandy Oceanfront1 / 46
    (3)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 23 September 2019
    My family just spent a fun filled week in Islamorada and our accommodations at Paradise Beach were fantastic! The house is impeccably designed with a pool that kept us outside...
    Reviewed 20 April 2019
    The house is beautiful, views are amazing, and it has everything you need or will ever need. Our whole family enjoyed a week of relaxation, and we spent some memorable time...
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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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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    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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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful Bayside View with Swimming Pool1 / 49
    (1)Excellent
    4.4 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Grill
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 May 2018
    My family just LOVED this house. The backyard is amazing with a beautiful view and plenty of space for boat-dockage. My family had fun paddle boarding, kayaking, and...
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    About this property
    Bayside View is truly an amazing Florida Keys home, with great Bay views from all floors! Bayside View is a 3 bedroom/3 bath home that is directly on the Florida Bay. This location satisfies all of your fishing & water sport desires. The home is completely renovated and absolutely gorgeous. The...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3.2 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    BEACON REEF 3101 / 21
    (5)Excellent
    4.5 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • Cable/satellite TV
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 2020
    It is comforting when you first check in to know everything you need is there on the property. More importantly the Keys Holiday Rentals personnel have gone out of there way to...
    Reviewed 23 February 2019
    We love staying at Beacon Reef and booking through Keys Holiday Rentals. The unit is nicely decorated and conveniently located in the complex. We have booked it again for next...
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    About this property
    <b> Minimum Rental: 28 Days </b> '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...
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    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    4.0 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    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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    Location Information
    Matecumbe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    OCEANFRONT pool30'Dock,7niteMin, 6ppl max,sorry no pets STANDADrate$465/nite1 / 51
    (6)Excellent
    3.3 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2014
    We had such a wonderful time at Paradise Point!! The views were beautiful!!! The kids loved the pool and all the sealife we saw. Many fish and stingrays, just to name a few...
    Reviewed 13 February 2014
    My week started when my wife and I along with our two friends met Juan Sanchez at this home he calls Paradise (which it really is). The man from my first e mail to him to...
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    About this property
    FOR ADDITIONAL REVIEWS GO TO 'HOMEAWAY.COM' LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS IF YOU GET A RESPONSE FROM BESTHOLIDAYRENTALS.COM **** IGNORE IT **** SCAM MINIMUM STAY 7 NIGHTS, MAXIMUM OCCUPANCY 6 PPL, NO PETS, RENTAL...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    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 panoramic ocean views from every room....
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    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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    • 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
    <b> Minimum Rental: 28 Days </b> '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...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Windy Cove #11 / 19
    (1)Excellent
    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
    Reviewed 7 July 2019
    We had the best time in Windy Cove #1!!!! This condo was perfect for us. Each bedroom was a nice size and the view was amazing!! Everything was clean and it was very...
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    About this property
    OFF SEASON SPECIAL ~ $1,200/ week (plus taxes & fees) if you stay with us from now until November 15 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...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    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
    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
    <b> Minimum Rental: 7 Days </b> 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....
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4.7 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    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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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    PALMS 3141 / 24
    (2)Excellent
    3.3 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • 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
    <b> Minimum Rental: 28 Days </b> '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...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    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
    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
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    About this property
    Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    LITTLE BAY - Cottage1 / 24
    (3)Very good
    3.3 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2019
    Loved the house and the key west feel. Beautiful kitchen and living area. Very comfy bed and nice master bath. The only reason I rated it a four was the water area. We really...
    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...
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    About this property
    <b> Minimum Rental: 7 Days </b> '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...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    SUNSHINE PLACE1 / 23
    (15)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
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2019
    hidden jewel in a sea of unattractive options.Sunshine place was absolutely perfect private residence, private access, large grounds with waterfront access and view to the...
    Reviewed 20 February 2019
    This house is perfect for a couple like us with a small dog. Nestled between 2 resort properties, Pelican Bay and Post Card Inn, the house is right on the water and the grounds...
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    About this property
    <b> Minimum Rental: 7 Days </b> '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...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    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
    <b> Minimum Rental: 28 Days </b> '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...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b> Minimum Rental: 7 Days </b> 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...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    BEACON REEF 4061 / 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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    • Internet Access
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Grill
    • Hot Tub
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2019
    Lovely decor with a breath-taking ocean view from the balcony. Readily accessible to a day in Key West, Key Largo, or Everglades National Park. Sport-fishing, snorkeling, or a...
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    About this property
    <b> Minimum Rental: 28 Days </b> 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...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    BEACON REEF 5221 / 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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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2019
    I stayed at Beacon Reef for the month of February and I loved it. The condo was very clean and the grounds and pool area were beautiful. The ladies at Keys Holiday Rentals were...
    Reviewed 5 January 2019
    Beacon Reef and Islamorada was beautiful. The condo was spectacular and the ocean front view amazing. The condo had a beautiful pool, dock, beach and gym! In terms of...
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    <b> Minimum Rental: 28 Days </b> 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...
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    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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
    <b> Minimum Rental: 28 Days </b> '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...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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
    <b> Minimum Rental: 28 Days </b> '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...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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)
    • Parking
    • 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
    <b> Minimum Rental: 28 Days </b> '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...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    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)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    BEACON REEF 5011 / 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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    • Grill
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2019
    Love everything about Beacon Reef! Keys Holiday Rentals goes above and betond to make sure their guest are happy and comfortable.
    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 STAY: 28 Days. 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 gutted and totally remodeled in 2013 - granite counters, stainless steel...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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
    <b> Minimum Rental: 28 Days </b> '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...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    VILLA RIOLO1 / 22
    (3)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 5 March 2020
    This was our second visit. We were here last year for a month and came back this year for two months. Keys Holiday Rentals couldn't be any better. There respond immediately...
    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...
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    About this property
    <b> Minimum Rental: 28 Days </b> '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...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4.6 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 3 Bathrooms, Sleeps 6 MINIMUM STAY REQUIRED - NOT A SHORT TERM RENTAL - PLEASE CONTACT US FOR SPECIFIC DATES, AVAILABILITY AND RATES. Every time we stay, we never want to leave. 3 story bayside villa with its own beach. Great location. Views of both the Bay and the Ocean. Three good...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    PALMS 4171 / 24
    (1)Excellent
    3.2 miles from Bud n' Mary's Sportfishing Marina
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Hot Tub
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b> Minimum Rental: 28 Days </b> 'The Palms #417' has great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    3.3 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Grill
    • Washer
    • Cable/satellite TV
    • Ocean Views
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WE ARE A WONDERFUL WATERFRONT HOME IN THE HEART OF ISLAMORADA FLORIDA! WATCH THE MANATEES AND TARPON- WEEKLY STAYS ARE WELCOME, WE ARE FULLY LICENSED FOR WEEKLY STAYS. NEW SAMSUNG HD 4K TELEVISION, PRIVATE PROTECTED DOCKAGE. DIRECT OCEAN ACCESS, NEWLY PAVED PRIVATE ROAD. HIGH SPEED WIRELESS...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 4
    3.0 miles from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 3 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
    The dream home away from home. The upstairs main floor offers two large bedrooms with cozy king beds, two full baths, a beautifully decorated open concept living and dining room, updated kitchen and great outdoor living area. Pool and canal views from not only the expansive screened-in balcony, but...
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    Location Information
    Layton, Long Key
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2.7 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
    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
    4.1 miles from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
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    • Air Conditioning
    • Waterfront
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Directly on your private oceanfront beach. Ocean views from every room of your two bedroom one bath Keys style duplex villa.You will experience the true 'old Keys' charm of bird watching on the wraparound deck to fishing on the beach...or perhaps just relaxing on the sand.With over a half acre of...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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