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Holiday Homes near Rain Barrel Village

86700 Overseas Hwy, Mile Marker 86.7, Bayside, Islamorada, Florida 33036-3138
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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 68 Rentals in Islamorada
    Newly refinished  condo open water views very nice1 / 16
    (6)Excellent
    2.3 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2.5 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    2.5 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Bayside Condo, marina, pool and beach1 / 35
    (17)Very good
    2.4 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Balcony
    • Terrace
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2018
    We recently rented this condo unit for a week for our family of six. It accommodated us great, 3 bedrooms plus a pull out couch. Outside was beautiful, very clean and well...
    Reviewed 14 March 2018
    Love staying in this condo was our second year hoping to return next winter if available. already made request.. I would never leave if it were up to me but the location and the...
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    About this property
    Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for...
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    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    THE PERFECT GETAWAY1 / 14
    (6)Very good
    1.3 kilometres from Rain Barrel Village
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Hot Tub
    • Washer
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    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2016
    My husband and I searched for six weeks to find the perfect house for our vacation with another couple, and kept coming back to this one. All four of us were looking for a...
    Reviewed 10 April 2016
    We thoroughly enjoyed staying at the Perfect Getaway. My family and I had enough space to sleep, relax and enjoy meals together. The pool was a great addition to the property...
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    About this property
    This four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. It is situated in a clean, upscale neighborhood of all waterfront homes. The house is equipped with all the comforts of home. It is modernly furnished. Upstairs there are...
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    2.5 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Washer
    • Waterfront
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anglers Reef Villa Resort 2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating,...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1.5 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is called the Cypress house.  It has been an Islamorada family getaway for the last 19 years.   Venetian Shores is a commumity in Islamorada which is a beautiful, quiet neighborhood perfect for strolling, jogging and bicycling. There is parking for four vehicles and space to store a...
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    Matecumbe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.5 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    • Grill
    • Waterfront
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, back yard patio with barbecue, front porch seating, and balcony. Boat slip can be...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1.4 kilometres from Rain Barrel Village
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for an amazing home in Venetian Shores? This beautifully updated 4 bedroom, 4 bath home has everything you need for a perfect vacation. This home is suited for entertaining, with a spacious kitchen, open living and dining room and large screened in porch overlooking the canal. The 3rd...
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    107 San Remo Drive1 / 36
    (2)Excellent
    1.3 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    Reviewed 25 May 2019
    This house is perfect if you want to be close to everything. Tons of great restaurants within 5 minutes. Dock for your boat and lots of seating outside and on the screened porch...
    Reviewed 29 January 2018
    What a fabulous area and home, Nancy and Norm were (the owners) told us places for dining out, Island times grill, Craigs seafood ( Mahi Mahi sandwich is to die for) Mrs Mac...
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    About this property
    Comfortable Venetian Shores canal home that has two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs. The downstairs apartment has a complete kitchen and living room and separate bedroom. There is a screened in porch of the living room upstairs. The home has awesome...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.3 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.7 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    This townhome at Executive Bay will sure make your home away from home!  This unit has been completely renovated and decorated beautifully.  This 2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 32
    (3)Excellent
    1.5 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2018
    I was having trouble booking my reservation online (technicality), and had to call in for help. One of the girls there was able to help me quickly, booked me & took my payment...
    Reviewed 2 February 2016
    We loved our stay at Ocean Harbour Apartments. After viewing photos on your website, we chose this based on the beautiful grounds and lovely accomodations. We could not have...
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    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
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    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    2.0 kilometres from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Children's Pool
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    Everything was perfect. Weather was great, the unit was clean and fully furnished with everything we needed. The other vacationers and full-time residents were friendly and...
    Reviewed 6 May 2016
    This condo was to die for. The decor was fabulous and the location was perfect and close to many restaurants. The sunset from the balcony was breathtaking. The owner was a...
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    About this property
    Beautiful / tropical decorated one bedroom, one bath water front condo in Summer Sea Condominiums located at Mile Marker 88.5 Bayside Islamorada, FL. Bayside means amazing open water views & world famous Florida Keys sunsets from your own private balcony overlooking the Florida Bay. You can also...
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    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2.5 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Children's Pool
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    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1.6 kilometres from Rain Barrel Village
    4 Bedrooms, 5 Bathrooms, Sleeps 8 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
    This is a beautiful Venetian Shores home... It truly is a must see! The interior is clean and nicely decorated. The large porch on the back allows you to see the famous Florida Keys sunsets from your own home! Located a few houses down from Snake Creek, you'll have quick ocean and bay access. Deep...
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Islamorada Luxury Home Ocean & Bay Access1 / 14
    (9)Excellent
    2.0 kilometres from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • Waterfront
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF1 / 25
    (1)Excellent
    2.6 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2016
    Everything we expected and more!! Condo very well maintained. Very adequately supplied with everything you need during your stay. Wonderful!! Thank you Susie and Matt for...
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    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool1 / 37
    (3)Excellent
    1.3 kilometres from Rain Barrel Village
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2020
    Perfect vacation house on the ocean, close to everything. The spacious house was immaculate when we checked in. The owner was extremely friendly and responsive. It was perfect...
    Reviewed 29 April 2019
    The location, the amenities, the house, and the pool area was perfect. Everything needed to spend a weeks vacation with your family is within this home. I bring my 3 grown...
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    About this property
    Beautiful Gated Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding Staircase, Expansive Ocean Views, Over 4000 Sq. Ft. of Living Space. Heated Pool, Sandy Back Yard, Gated Entrance Lined With Palm Trees. Enjoy the Ocean Views and...
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    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    2.4 kilometres from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Terrace
    • DVD Player
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ****Recently updated paint, furniture and a Beauty Rest Mattress!!**** Looking to escape reality? Look no further! Spacious 1 bedroom/1 bathroom condo located in the newly renovated Summer Seas Condominiums. Sit back and relax at the pool, go swimming at the private beach. Feeling adventurous?...
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    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    2.5 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Keys home in Anglers Reef with ocean view, dock, community pool & private beach This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    2.5 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • Secure Parking
    • Washer
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This magnificent home with direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Lie in bed and view the Ocean! Home also overlooks the community pool. Anglers Reef is a quiet oceanfront...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    LYONS LANDING1 / 25
    (1)Excellent
    1.7 kilometres from Rain Barrel Village
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
    • Terrace
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2017
    Every room is comfortable,charming and the property managed to make you feel comfortable and at home..with every amenity..including an ice maker..so nice to have here in The...
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    About this property
    <b> Minimum Rental: 28 Days </b> 'Lyons Landing' is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home. 3 bedrooms and two baths on the upper level plus a...
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    1.6 kilometres from Rain Barrel Village
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on...
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    FLAMINGO COTTAGE1 / 22
    (1)Excellent
    0.4 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Grill
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 February 2020
    The flamingo cottage was as advertised. Comfortable surroundings, beautiful pool, private sunbathing areas and beautiful ocean view.
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    About this property
    <b>MINIMUM STAY: 28 DAYS </b>'Flamingo Cottage' is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Oceanfront Anglers Reef Islamorada Florida Keys1 / 2
    (3)Very good
    2.5 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
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    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 2018
    This home is in a gated community in the heart of Islamorada. The site is beautiful, and seemed to have suffered no damage from Hurricane Irma. There are two artificial...
    Reviewed 25 August 2017
    Very well appointed and comfortable house, conveniently located to local amenities in Islamorada. It was like a home from home with easy to use washing machine, dryer and...
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    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!1 / 34
    (1)Excellent
    2.4 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Housekeeping Included
    • Waterfront
    • Wi-Fi
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    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2020
    Our first visit to the Florida keys and we wanted explore! But, I like to have my conveniences (ok, I hate sleeping in a tent!) This condo was quiet-Loved that! Islamorada is...
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    About this property
    Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    2.2 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Smoking allowed
    About this property
    Welcome to Modern Keys Living with Bay Views! New from top to bottom!!! Newly remodeled and beautifully decorated 1st floor corner unit with a private entrance. Enjoy the mix of vintage and new furniture and the most comfortable sofas, beds, linens and more! This home is equipped with everything...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.4 kilometres from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Located on a quiet street in Islamorada, this home offers you the best of both worlds.  Fantastic Protected canal dockage with an Awesome Bay View!  This multilevel home offers 3 bedrooms and 3 baths.  Upstairs, on the first level, is your kitchen, living room, and a bedroom with Trundle Beds.  The...
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    Location Information
    Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Mile Marker 87 - Mina Bay - Oceanfront 'Million Dollar View'1 / 38
    (2)Excellent
    0.7 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Washer
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    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 March 2017
    We spent part of the holidays at Mina Bay! The views are stunning! Not to mention you can hear the sound of the waves from the second bedroom - very relaxing! The unit is...
    Reviewed 25 January 2017
    Beautiful spacious oceanfront condo fully detailed and furnished in a gated community in Islamorada. The location is perfect and the beach is on the doorstep. Perfect for two or...
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    About this property
    Mina Bay - vacation rental with 'the million dollar view'! Truly BAYFRONT on the sandy beach and feet from the pier and dock. Sparkling water's and brilliant sunsets complete this 2 Bd 1.5 Ba plus loft Unit I-1 townhouse. 28 DAY MIMIMUM RENTAL for all guests.  Accommodates a family of 8 perfectly...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    0.7 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Patio
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Executive Bay Club Condo P-3 Come spend your next island family vacation in this newly-remodeled and nicely decorated home. The community features great, family-friendly amenities including a private community beach with amazing sunsets, a fishing dock, two tennis courts, a beautiful...
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    Matecumbe Key, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.5 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
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    • Balcony
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful and spacious home with three bedrooms, two and half baths, huge new kitchen, new bathrooms, and screened in porches facing East and West. There are great views from every room!!! Tastefully furnished with all linens, comfortable memory foam mattresses, all new appliances, and completely...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2.3 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
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    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dock of the Bay The condo is located in the Futura Yacht Club and boasts a plethora of amazing amenities that you'll be able to enjoy during your stay including a heated pool, two lighted tennis courts, basketball and sand volleyball courts, and great areas to grill and picnic! You won't want to...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    2.2 kilometres from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Children's Pool
    • Cable/satellite TV
    • Secure Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'BREATHTAKING sunset views' from this beautifully decorated one bedroom, one bath, bay front condo in Summer Sea Condominiums located at Mile Marker 88.5 in Islamorada, FL. View the Keys amazing tropical sunsets and famous turquoise/blue waters from the comfort of your bedroom, living room, or...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Islamorada cottage on deep water canal1 / 15
    (2)Excellent
    2.5 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
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    • Waterfront
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    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 February 2020
    My husband and I thoroughly enjoyed our stay. The apartment was very clean and most comfortable. Well-stocked kitchen, included dishwasher & wine cooler. Screened-in porch...
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    About this property
    Our cottage is located in a quaint and quiet neighborhood on a deep water canal, Bayside at Mile Marker 89. A concrete boat dock is available for a 30 foot boat and a fish cleaning station. There is easy ocean access through Snake Creek or Tavernier Creek. The fenced private back garden has a...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.4 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a 2 bedroom and 2-1/2 bath unit.  There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    0.7 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
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    • Internet Access
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2.4 kilometres from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 3 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
    This 1 bedroom/1 bath condominium is located in Summer Sea in Tavernier. This is a gated complex located directly on the Florida Bay at Mile Marker 88.5, which is within the Village of Islamorada. The unit has a stunning view of the bay from the living room, master bedroom and the balcony. It...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    0.6 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Terrace
    • Washer
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    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sleeps 8, 2 Story Townhome On The Bayside, Mile Marker 87 Our Islamorada beach modern decorated townhome is waiting for you. It’s a two story unit and third level loft; 2 Bedroom/2 Bath - sleeps 8. Next door is Founders Park & Plantation Yacht Harbor. A private gated community with 24hr...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    2.4 kilometres from Rain Barrel Village
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    The most spectacular bay views from this stunning Islamorada home. This newly remodeled home offers 3 bedrooms and 2 baths upstairs with a beautiful kitchen and spacious living room overlooking the bay. Downstairs there is one bedroom and one bathroom, with another living room for guests. This...
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    Location Information
    Matecumbe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2.4 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming 2 bedroom, 2.5 bath condo with ocean views, a sun room for a dining room, and newly renovated kitchen. Enjoy your coffee as you watch the sunrise over the Atlantic Ocean on your balcony or sit and relax in the pool. This great complex also offers a fantastic view of the Florida Keys from...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    0.7 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful two story townhome in a private, gated community with all of the amenities you'd expect while on vacation. Inside: Newly renovated and remodeled unit. Fully equipped kitchen and stainless appliances, large storage cabinets with pull outs. Granite counters etc. Living room area with 60...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.4 kilometres from Rain Barrel Village
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * TurnKey photo-verifies this home is professionally cleaned with products approved by the EPA for use against COVID-19. * Situated on the beautiful Florida Bay, this 3BR/2BA Islamorada home offers an idyllic waterfront haven with its own private beach, dock, kayak, paddleboards, and sprawling...
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    Matecumbe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2.3 kilometres from Rain Barrel Village
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    This unit's kitchen, bathrooms, windows, and doors received a facelift in January 2014! Enjoy the spectacular view of the Florida Bay from either one of the TWO balconies in this 2 story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, flat panel TV's in...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    1.5 kilometres from Rain Barrel Village
    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
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
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    Location Information
    Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.2 kilometres from Rain Barrel Village
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An adorable decorated studio apartment that has everything you need for your stay in the keys. Summer Seas is a gated complex and it offers a great pool, beach, work out room, game room and billiards. Its bay side location you will allow you to enjoy the spectacular keys sunsets. Summer Seas Condo...
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    Tavernier, Key Largo
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    2.1 kilometres from Rain Barrel Village
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Hot Tub
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Grill
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    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b>MINIMUM STAY: 28 DAYS </b> Fish Whistle is an amazing privately owned estate located directly on Snake Creek in Islamorada. It offers spectacular views and easy access to the Atlantic Ocean or Florida Bay for either sport fishing or diving/snorkeling activities. This home comfortably sleeps...
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    Location Information
    Matecumbe Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    0.8 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    Come to Paradise and Enjoy it with Comfort! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.5 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Premier condo in Islamorada in Upper Florida Keys. Located on 12-acre property with 1,100 feet of oceanfront. Gated complex, large swimming pool, sand beach, and two tennis courts as well as boat ramp and dedicated slip. Spectacular Atlantic Ocean views. This top-floor, freshly-remodeled 2 bed 2...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.3 kilometres from Rain Barrel Village
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Patio
    • Washer
    • Balcony
    • Cable/satellite TV
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    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedroom / 2 bath / light and airy - large balcony backing up to a quiet nature preserve. Perfect home for a getaway! Centrally located in gorgeous Islamorada. Two bedroom / two bath. Gorgeous private homeowners beach and private dock, close to the best restaurants, and sightseeing. Our home...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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