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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 July dates now. Secure your holiday rental today, and have the perfect trip.
    All 80 Rentals in Islamorada
    ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE1 / 17
    (9)Excellent
    7.3 kilometres from Bud n' Mary's Sportfishing Marina
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    75731 Overseas Highway1 / 32
    (13)Very good
    6.4 kilometres from Bud n' Mary's Sportfishing Marina
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    75130 Overseas Highway1 / 19
    (6)Excellent
    7.3 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    76004 Overseas Highway1 / 35
    (5)Excellent
    6.0 kilometres from Bud n' Mary's Sportfishing Marina
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Reviewed 26 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 detached 2 bedroom 1 bathroom apartment. The home is located at mile marker 76....
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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
    5.4 kilometres 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 31 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
    Ocean-Front Caribbean Home.1 / 21
    (3)Excellent
    3.5 kilometres 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 23 March 2021
    This place is amazing, in the heart of everything but still has some of the old charm. Pool, boat ramp, dockage, fishing from the dock, ice machine, trailer parking all on...
    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...
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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
    132 Columbus Drive1 / 18
    (17)Very good
    5.1 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 1 April 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 12 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
    137 LeSerra Lane1 / 34
    (9)Very good
    5.4 kilometres from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Reviewed 11 September 2020
    This house was perfect for our family of six's week in the Florida Keys. The house's location features outstanding views of the ocean and is in a quiet area off of the Overseas...
    Reviewed 26 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...
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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
    6.2 kilometres 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
    82754 Overseas Highway1 / 29
    (4)Excellent
    4.6 kilometres 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 8 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 10 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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    Paradise Beach Sandy Oceanfront1 / 46
    (4)Excellent
    6.4 kilometres from Bud n' Mary's Sportfishing Marina
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Wi-Fi
    • Washer
    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2020
    We loved staying at Paradise Beach! It was a welcome change from our new Covid lifestyle. The house was very clean and had everything we needed for kids and adults to relax and...
    Reviewed 24 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...
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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
    7.3 kilometres 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 14 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 23 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
    5.2 kilometres 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
    (6)Excellent
    7.3 kilometres 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 26 December 2020
    Islamorada really is a sweet spot on the keys. Much nicer than Marathon, tons of high end restaurants, fishing charters everywhere. This complex is spotless, large heated pool...
    Reviewed 12 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...
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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
    6.5 kilometres 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
    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
    PALMS 3091 / 25
    (3)Excellent
    5.3 kilometres 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 12 December 2020
    This was our 2nd year of renting unit #309 at The Palms in Islamorada. The unit was immaculate and well stocked to make our month-long stay relaxing and enjoyable! The Palms...
    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.
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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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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    5.6 kilometres 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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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    5.3 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • 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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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    7.5 kilometres 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)
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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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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    PALMS 3141 / 24
    (2)Excellent
    5.3 kilometres 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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    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    4.3 kilometres from Bud n' Mary's Sportfishing Marina
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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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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    Islamorada, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    LITTLE BAY - Cottage1 / 24
    (3)Very good
    5.3 kilometres 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 5 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
    (16)Excellent
    5.3 kilometres 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 16 December 2020
    We just finished booking our third time at Sunshine Place for 2021. It has the most beautiful view for a sunrise you will ever see. The kitchen has everything you need to cook...
    Reviewed 12 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...
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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 kilometres 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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    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    LITTLE BAY - Lower Duplex1 / 23
    (4)Excellent
    5.3 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Grill
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    • Patio
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    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
    5.4 kilometres 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 24 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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    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    BEACON REEF 5221 / 25
    (2)Excellent
    5.4 kilometres 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 25 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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    About this property
    <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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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    BEACON REEF 2221 / 25
    (2)Excellent
    5.4 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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 14 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
    5.3 kilometres 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
    5.7 kilometres from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 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 10 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
    BEACON REEF 5011 / 25
    (2)Excellent
    5.4 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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 5 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
    VILLA RIOLO1 / 20
    (3)Excellent
    5.1 kilometres 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 6 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 22 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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    <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
    PALMS 4171 / 24
    (1)Excellent
    5.2 kilometres from Bud n' Mary's Sportfishing Marina
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • 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 2
    7.5 kilometres 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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    5.4 kilometres from Bud n' Mary's Sportfishing Marina
    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 4
    4.3 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    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
    0.1 kilometres 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)
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Palms of Islamorada is a private oceanfront condominium overlooking Alligator Lighthouse. This beautiful condo offers spectacular ocean views as soon as you walk through the front door. With an updated kitchen, open concept layout and a balcony overlooking the pool and ocean, this is the...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    0.1 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
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    Amenities & Details
    • Hot Tub
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b> Minimum Rental: 28 Days </b> 'The Palms #407' is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    PALMS 3011 / 24
    (1)Very good
    5.2 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 2018
    Condo was as advertised. Great location. The pool was very nice and the view from the "beach" area was amazing...but not a beach, concrete. The complex is larger than...
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    About this property
    <b> Minimum Rental: 28 Days </b> 'The Palms #301' is an exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.1 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
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    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Parking
    • Patio
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Heated)
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b>MINIMUM STAY: 1 Month </b> Spectacular oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Alligator Reef Lighthouse is easily visible from your master suite or the balcony and you'll be able to watch cruise ships as they pass by...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.1 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
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    Amenities & Details
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b>NEW LISTING</b> Minimum Rental 1 month. This is an exceptional 2 bedroom and 2 bath condo located in one of the most popular Islamorada condo complexes - The Palms of Islamorada. The balcony is large enough to dine or recline and offers fabulous open water views. While sipping coffee in...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.1 kilometres from Bud n' Mary's Sportfishing Marina
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Hot Tub
    • Internet Access
    • Patio
    • Parking
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b> MINIMUM RENTAL: 1 Month </b> The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features separate his and hers mini-gyms, heated pool, hot tub, tiki for gatherings and lots of lounge chairs so soaking up the wonderful...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    3.7 kilometres from Bud n' Mary's Sportfishing Marina
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 7 Nights Saturday to Saturday The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each home offers two private bedrooms. Between the two homes there is sleeping for 10 in beds plus an additional 2 on the sleeper sofa...
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    Location Information
    Matecumbe Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    5.4 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
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    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Grill
    • Patio
    • Parking
    • Internet Access
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b> Minimum Rental: 1 Month </b> Enjoy a relaxing stay here in the Keys at this immaculate and charming two bedroom and two bath condo. While the owners attend to their other property 'up north' you can relish all the delightful amenities of their condo. This unit is beautifully appointed...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    5.4 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Patio
    • Parking
    • Terrace
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: TWO MONTHS Immaculate townhouse in prestigious Sunset Hammock in Tavernier. You'll enjoy your time in the Keys in this charming and spacious two-story townhouse. Relax on one of the overstuffed sofas or casual chairs in the spacious living room. Open the sliding doors to the...
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    Location Information
    Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    5.4 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
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    Amenities & Details
    • Parking
    • Grill
    • Private Outdoor Pool (Heated)
    • Terrace
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 28 DAYS NEW TO RENTAL MARKET 'Beacon Reef 301' is a fully renovated condo that offers inspiring tropical views including the ocean from the open-air balcony accessed from the main living area and the master bedroom suite. This charming, clean, spacious 2 bedroom 2 bath condo has...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    5.4 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Parking
    • Balcony
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 28 DAYS FIRST TIME ON RENTAL MARKET. This exquisite condo has been TOTALLY remodeled and updated from top to bottom. This is a 5th floor unit with ocean views from the balcony and master bedroom suite. The furnishings are all brand new. There are three TV's - one to suit...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Little Bay Compound1 / 17
    (2)Excellent
    4.3 kilometres from Bud n' Mary's Sportfishing Marina
    5 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 December 2020
    My family, consisting of 9 adults ,rented the entire compound for Christmas week. The property is magnificent. We were able to have plenty of room to spread out and enjoyed...
    Reviewed 20 June 2019
    We searched for a perfect spot for our wedding, and we found it here. The compound was large enough for 16 people. The home and cottage were in great shape with everything you...
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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, accommodating a total of 18 people. The Upper Duplex &...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 18
    4.3 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Upper Duplex is a 1,500 sq ft unit with 2 bedrooms, 2 full...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    7.3 kilometres from Bud n' Mary's Sportfishing Marina
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check-in Check-out
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    Payment Protection
    Amenities & Details
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 2 bedroom 2 bath, condo with everything that you need for a perfect relaxing vacation. Balcony access off your living room and master bedroom that overlooks the newly remodeled pool and jacuzzi as well as the beach and ocean. The complex is oceanfront and this unit has ocean views. Some...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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