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Holiday Rentals near Robbie's of Islamorada

77522 Overseas Hwy, Islamorada, Florida 33036-3813
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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Islamorada
    Newly refinished  condo open water views very nice1 / 16
    (6)Excellent
    7.1 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Modern Executive Bay Club Townhouse with Pool & Beach1 / 28
    (3)Very good
    5.5 kilometres from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3.5 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Family Friendly Executive Bay Townhome with Beach & Pool1 / 28
    (10)Excellent
    5.5 kilometres from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2015
    We attended with my wife and adult daughters and this apartment had everything we could wish for.The facilities were ideal for our needs and the booking process was simple.Due...
    Reviewed 13 September 2015
    The condo is very nice and spacious for 5 persons. The place is clean and supplies are adequate. Location is good. Swimming pool is big and nice. Able to do a little fishing...
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    7.1 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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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
    5.5 kilometres from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Grill
    • Balcony
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Executive Bay Club at mile marker 87 is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a heated pool, a clubhouse, a private beach area and a fishing dock. The waters are filled with plant and marine life,...
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    Matecumbe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.5 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relaxation at its best awaits you in our beautiful, Keys townhome on mile marker 87. Executive Bay Club is located in Islamorada, the Sports Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a heated swimming pool, a clubhouse, a private beach...
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    Matecumbe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5.5 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Parking
    • DVD Player
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach area and a...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    5.5 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3.6 kilometres from Robbie's of Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for an amazing home in Venetian Shores? This home has everything - 4 bedroom, 4 bath home that has been updated. The kitchen is amazing, suited for any type of entertaining. The 3rd floor floor is a lofted master bedroom suite with a walk-in closet. Two guest bedrooms are located on the...
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    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    107 San Remo Drive1 / 36
    (2)Excellent
    3.5 kilometres from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    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
    7.0 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfect catch and enjoy a sunset...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    7.1 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Wi-Fi
    • Grill
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coral Harbour Condo Enjoy excellent ocean and lagoon views from your furnished patio! This top-floor condo is located in the Coral Harbour Club, which is one of Islamorada's best-kept complexes. This community is located right on the water and offers marina access and use of a slip capable of...
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    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    7.1 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Balcony
    • Ocean Views
    • Terrace
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    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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    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Bayside Condo, marina, pool and beach1 / 70
    (17)Very good
    7.2 kilometres from Robbie's of Islamorada
    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 10 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
    5.5 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • Parking
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and relax at our beautiful townhome on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sports Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach area and a...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    No dockage allowed. Florida Keys. Beautiful condo. Short walk to the beach area.1 / 18
    (7)Excellent
    5.5 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2016
    This was our first trip to Florida, it was agreed that we would leave Orlando and the parks for a few years as our children are still quite young (4 and 1). We did extensive...
    Reviewed 18 January 2016
    We had very nice time staying in Ana's townhouse in Islamorada. It is nicely decorated, well equipped, comfortable and spotlessly clean. There is more than enough room for a...
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    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Ocean-Front Caribbean Home.1 / 21
    (2)Excellent
    2.8 kilometres from Robbie's of Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Washer
    • Balcony
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 March 2018
    Very much enjoyed our stay. House was beautiful and clean, staff was friendly and helpful. My mother and I loved relaxing in the hot tub and my father and husband very much...
    Reviewed 25 April 2015
    Rolled out of bed early every day this week with my boys and family friends for my favorite commute: 50 yard walk to a private boat slip at the resort. We rented a boat...
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    About this property
    The Royal Palm, South - Ocean Front Home Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Full kitchen with Subzero appliances and Viking stove. Chiseled-rock flooring throughout. Wrap-around verandas. Seamless curved-glass corner windows. High open-beam ceilings. Located on The...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    5.5 kilometres from Robbie's of Islamorada
    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
    THE PERFECT GETAWAY1 / 14
    (6)Very good
    3.7 kilometres from Robbie's of Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 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 9 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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    82754 Overseas Highway1 / 29
    (4)Excellent
    1.6 kilometres from Robbie's of Islamorada
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    We have been staying in the keys for 5 years in a row & this was the best rental property we found. We are 4 guys (over 50) who want to go fishing and relax and this property...
    Reviewed 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
    2.3 kilometres from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Washer
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    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, private back yard terrace with barbecue, front porch seating, balcony, and dock....
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    7.2 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE KING MASTER BEDROOM IS DRESSED IN ISLAND FINERY WITH PRIVATE BATHROOM, COMBINATION SHOWER/TUB, AND FLAT SCREEN TV MAKES FOR THE PERFECT RETREAT. THE SECOND BEDROOM OFFERS A QUEEN SIZE BED, A FLAT SCREEN TV, AND AN ATTACHED BATHROOM. YOU CAN “COOK YOUR CATCH” IN THE FULLY EQUIPPED KITCHEN WITH...
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    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    3.3 kilometres from Robbie's of Islamorada
    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
    Windy Cove #11 / 19
    (1)Excellent
    1.2 kilometres from Robbie's of Islamorada
    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
    Reviewed 7 July 2019
    We had the best time in Windy Cove #1!!!! This condo was perfect for us. Each bedroom was a nice size and the view was amazing!! Everything was clean and it was very...
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    About this property
    OFF SEASON SPECIAL ~ $1,200/ week (plus taxes & fees) if you stay with us from now until November 15 Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    BEACON REEF 3101 / 21
    (4)Excellent
    0.9 kilometres from Robbie's of Islamorada
    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 23 February 2019
    We love staying at Beacon Reef and booking through Keys Holiday Rentals. The unit is nicely decorated and conveniently located in the complex. We have booked it again for next...
    Reviewed 2 November 2018
    Loved our stay in this beautiful condo! The view is spectacular! Condo is well stocked with all of your needs for a wonderful vacation in Islamorada!!! Highly recommend this...
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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
    PALMS 3091 / 25
    (2)Excellent
    1.0 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Parking
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2018
    Last year we spent 3 months in this location, and we enjoyed it so much we increased our stay to 4 months this year. Close to restaurants and marinas.
    Reviewed 17 August 2017
    Our three month stay was excellent. We enjoyed the location and close proximity to where we had our boat stored.
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    About this property
    <b> Minimum Rental: 28 Days </b> 'The Palms #309' is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    1.0 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Patio
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2013
    We have rented the upper duplex of Little Bay in April for the last few years. it is a beautiful property in a perfect setting. The grounds are kept immaculately and the area...
    Reviewed 5 November 2012
    We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach...
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    About this property
    <b> Minimum Rental: 7 Days </b> Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month....
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    6.8 kilometres from Robbie's of Islamorada
    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 10 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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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1.9 kilometres from Robbie's of Islamorada
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid 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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    7.1 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This tropically decorated 2 bedroom 2 bath unit, has a King bed and (2) Twins beds is approximately 1 hour and 20 minutes from Miami International Airport and 90 Minutes from Ft. Lauderdale airport.  Futura Yacht Club is located in the Village of Islamorada in the Upper Florida Keys. Located...
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    Location Information
    Tavernier, Key Largo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    LYONS LANDING1 / 24
    (1)Excellent
    3.6 kilometres from Robbie's of Islamorada
    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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Luxurious Anglers Reef with Boat Slip, Pool, Ocean1 / 29
    (26)Excellent
    2.2 kilometres from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Grill
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    We stayed at Angler's Reef and had an amazing time. Jo was very helpful with the booking and very easy to work with. We felt like we were at home in her rental. She has...
    Reviewed 11 July 2017
    The island is beautiful. The condo is so clean and high quality. The area is located on the water. Nice boat docks.
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    About this property
    House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    PALMS 3141 / 24
    (2)Excellent
    1.0 kilometres from Robbie's of Islamorada
    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
    1.2 kilometres from Robbie's of Islamorada
    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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Islamorada Luxury Home Ocean & Bay Access1 / 14
    (9)Excellent
    3.5 kilometres from Robbie's of Islamorada
    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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (4)Very good
    6.4 kilometres from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2018
    I was having trouble booking my reservation online (technicality), and had to call in for help. One of the girls there was able to help me quickly, booked me & took my payment...
    Reviewed 19 January 2018
    Yes there was..DO NOT RENT FROM ITRIP/PHOENIX RENTALS.They were totally dishonest with me. They did not tell me that there was major construction going on in the building I...
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    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    LITTLE BAY - Cottage1 / 24
    (3)Very good
    1.0 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Grill
    • Cable/satellite TV
    Suitability
    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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.6 kilometres from Robbie's of Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    ISLAMORADA Waterfront GREEN IVIS PARADISE Min 28 Ngts. Max 10 ppl. 26% Disc >1mo1 / 17
    (1)Excellent
    3.5 kilometres from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Balcony
    • Ocean Views
    • Grill
    • Washer
    • Waterfront
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2018
    We had. Great time. Can't wait to come back. The house was impeccable and the host gave us great customer service. Amazing time in the water. Great canal!
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    About this property
    Relax in this peaceful keys home with wide canal with easy access to ocean & bay. Located in one of the best neighborhoods in the keys!! You will enjoy a morning stroll, jogging or a bike ride around this picturesque neighborhood. We have plenty of room for your boat and all your toys. Bring or...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    SUNSHINE PLACE1 / 23
    (15)Excellent
    1.0 kilometres from Robbie's of Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Grill
    • Internet Access
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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...
    Reviewed 21 February 2019
    This house is perfect for a couple like us with a small dog. Nestled between 2 resort properties, Pelican Bay and Post Card Inn, the house is right on the water and the grounds...
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    <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
    Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool1 / 34
    (2)Excellent
    6.2 kilometres from Robbie's of Islamorada
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 17 April 2019
    We are three families that vacation together, everyone was just amazed at the expansive ocean views and the size of the property and home. The pictures do not do justice to it...
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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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    4.7 kilometres from Robbie's of Islamorada
    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
    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 / 14
    (3)Very good
    2.3 kilometres from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Patio
    • 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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    6.1 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b> Minimum Rental: 28 Days </b> 'The Palms #405' is a diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    LITTLE BAY - Lower Duplex1 / 23
    (4)Excellent
    1.0 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b> Minimum Rental: 7 Days </b> Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each...
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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.3 kilometres from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Children's Pool
    • Washer
    • Waterfront
    • Internet Access
    • DVD Player
    • 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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    Location Information
    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    BEACON REEF 4061 / 25
    (1)Excellent
    0.8 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Grill
    • Hot Tub
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 February 2019
    Lovely decor with a breath-taking ocean view from the balcony. Readily accessible to a day in Key West, Key Largo, or Everglades National Park. Sport-fishing, snorkeling, or a...
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    About this property
    <b> Minimum Rental: 28 Days </b> NEW ON THE RENTAL MARKET. 'Beacon Reef 406' is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient...
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    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    7.1 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rental amount includes all fees except boat dock fee. This newly renovated modern 3rd floor condo in Futura Yacht Club unit 302 is in a private gated community and has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened...
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    Location Information
    Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    BEACON REEF 5221 / 25
    (2)Excellent
    0.8 kilometres from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2019
    I stayed at Beacon Reef for the month of February and I loved it. The condo was very clean and the grounds and pool area were beautiful. The ladies at Keys Holiday Rentals were...
    Reviewed 5 January 2019
    Beacon Reef and Islamorada was beautiful. The condo was spectacular and the ocean front view amazing. The condo had a beautiful pool, dock, beach and gym! In terms of...
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    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
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