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Vacation Rentals near Florida Keys Watersports

85500 Overseas Hwy, on the bay side at Smugglers Cove Hotel & Restaurent, Islamorada, Florida 33036-3400
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    Travelers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 100 Rentals in Islamorada
    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    2.4 miles from Florida Keys Watersports
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    **Fall Promo** Modern Executive Bay Club Condo with Pool & Beach1 / 29
    (3)Very good
    1.6 miles from Florida Keys Watersports
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    No dockage allowed. Florida Keys. Beautiful condo. Short walk to the beach area.1 / 18
    (7)Excellent
    1.6 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    FALL SPECIAL DISCOUNTED PRICING!!!1 / 35
    (17)Very good
    2.6 miles from Florida Keys Watersports
    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 May 10, 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 March 13, 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
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    107 San Remo Drive1 / 36
    (1)Excellent
    0.3 miles from Florida Keys Watersports
    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 January 29, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.6 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 6 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 6
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    THE PERFECT GETAWAY1 / 14
    (6)Very good
    0.5 miles from Florida Keys Watersports
    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 October 2, 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 April 9, 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (4)Very good
    2.1 miles from Florida Keys Watersports
    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 July 25, 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 January 19, 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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    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront Anglers Reef Islamorada Florida Keys1 / 14
    (3)Very good
    0.3 miles from Florida Keys Watersports
    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 March 24, 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 August 24, 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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    **Fall Promo** Family Friendly Executive Bay Townhome with Beach & Pool1 / 29
    (10)Excellent
    1.6 miles from Florida Keys Watersports
    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 September 17, 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 September 13, 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
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    ISLAMORADA Waterfront GREEN IVIS PARADISE Min 28 Ngts. Max 10 ppl. 26% Disc >1mo1 / 17
    (1)Excellent
    0.3 miles from Florida Keys Watersports
    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 August 6, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    0.5 miles from Florida Keys Watersports
    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 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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.3 miles from Florida Keys Watersports
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    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
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    0.3 miles from Florida Keys Watersports
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    Prestigious Venetian Shores subdivision in Islamorada! This vacation home has 5 bedrooms and 3 bathrooms with 100'  concrete dock. The house is situated into two separate living quarters. Upstairs is a large master suite and 2 guest bedrooms, cathedral ceilings & fully stocked, eat-in kitchen,...
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    Islamorada, Florida Keys
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Luxurious Anglers Reef with Boat Slip, Pool, Ocean1 / 29
    (26)Excellent
    0.4 miles from Florida Keys Watersports
    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 August 19, 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 July 10, 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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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    1.6 miles from Florida Keys Watersports
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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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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    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.3 miles from Florida Keys Watersports
    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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    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.3 miles from Florida Keys Watersports
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Ocean Views
    • Cable/satellite TV
    • Grill
    • Washer
    • DVD Player
    • Air Conditioning
    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 patio with barbecue, front porch seating, balcony, and dock. Boat...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.6 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    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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    Tavernier, Key Largo
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.5 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Islamorada Luxury Home Ocean & Bay Access1 / 14
    (9)Excellent
    0.6 miles from Florida Keys Watersports
    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.3 miles from Florida Keys Watersports
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • DVD Player
    • 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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.6 miles from Florida Keys Watersports
    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
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    0.3 miles from Florida Keys Watersports
    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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    BEACON REEF 2221 / 25
    (2)Excellent
    2.3 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Balcony
    • Hot Tub
    • Parking
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 22, 2018
    We have so much enjoyed staying in this condo, Beacon Reef 222. The condo is very comfortable with a great kitchen and living area. The master bedroom is amazing with a large...
    Reviewed July 13, 2017
    Great location! The pool, tiki bar and dock are all top notch. The ocean views are amazing. All equals the perfect family vacation.
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    About this property
    ***FALL SPECIAL*** RECEIVE 10% OFF RENT FOR ALL BOOKINGS IN OCTOBER AND NOVEMBER. Minimum Rental: 28 Days 'Beacon Reef 222' is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below....
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2.6 miles from Florida Keys Watersports
    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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    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    BEACON REEF 3101 / 21
    (2)Excellent
    1.2 miles from Florida Keys Watersports
    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 1 week ago
    Can't say enough great things about our stay at Beacon Reef 310!! From the moment you walk into the condo we knew we loved it, The whole place had that bright tropical feel...
    Reviewed October 3, 2017
    Super clean and very comfortable condo! Property Managers were so easy to work with too! We loved Beacon Reef and had the best vacation!
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    About this property
    ***FALL SPECIAL*** RECEIVE 10% OFF RENT FOR ALL BOOKINGS IN SEPTEMBER, OCTOBER AND NOVEMBER. Minimum Rental: 28 Days 'Beacon Reef 310' is located in one of the most desirable condominium complexes in the Upper Keys. Convenient to everything - restaurants, fishing, diving, snorkeling, swim...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.7 miles from Florida Keys Watersports
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    About this property
    This beautiful 4 bedroom 4.5 bath home has everything you need to make your vacation perfect. This gorgeous Venetian Shores home has the perfect open concept layout, large kitchen and living room, even a game room with a pool table. But there's more! This home comes with a large master bedroom...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    2.6 miles from Florida Keys Watersports
    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    PALMS 3091 / 25
    (2)Excellent
    2.4 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 23, 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 August 17, 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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    ***FALL SPECIAL*** RECEIVE 10% OFF RENT FOR ALL BOOKINGS IN SEPTEMBER, OCTOBER AND NOVEMBER. Minimum Rental: 28 Days 'The Palms #309' is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1.6 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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    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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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Newly refinished  condo open water views very nice1 / 17
    (4)Excellent
    2.6 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 4, 2017
    Besides the obvious gorgeous outdoor surroundings, this condo was equally as beautiful. It's hard to be inside when you're in the Keys, but Mark's condo makes it easy. The views...
    Reviewed January 29, 2017
    The condo was beautiful and well appointed. The community was beautiful with a great pool, nice beach, and extremely friendly people. Great restaurants and a cozy deli nearby...
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    About this property
    Beautiful professionally decorated superior condo in the best location in Islamorada. The unit is superior with the best water views, with everything you need ,full kitchen stocked with cookware, microwave, coffeemaker, large island counter, breakfast nook with ocean view, washer and dryer in...
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    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    PALMS 2141 / 24
    (1)Excellent
    2.4 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    • Internet Access
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 2015
    We have always enjoyed the keys and love staying at the Palms of Islamorada. The units are big enough and the amenities are nice. Unit 214 was nice and clean. A big TV for me...
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    ***FALL SPECIAL*** RECEIVE 10% OFF RENT FOR ALL BOOKINGS IN SEPTEMBER AND OCTOBER. Minimum Rental: 28 Days 'The Palms #214' is a gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master...
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    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    82754 Overseas Highway1 / 29
    (4)Excellent
    2.8 miles from Florida Keys Watersports
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Reviewed June 7, 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 May 9, 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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    Location Information
    Islamorada, Florida Keys
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    2.6 miles from Florida Keys Watersports
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    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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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    0.7 miles from Florida Keys Watersports
    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 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF1 / 25
    (1)Excellent
    0.4 miles from Florida Keys Watersports
    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 November 9, 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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2.5 miles from Florida Keys Watersports
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
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    Pet friendly
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    Smoking allowed
    About this property
    Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in the beachside pool. The front home sits...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    PALMS 4171 / 25
    (1)Excellent
    2.5 miles from Florida Keys Watersports
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    • Terrace
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #417' has great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters...
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    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    LITTLE BAY - Lower Duplex1 / 23
    (4)Excellent
    2.4 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Minimum Rental: 7 Days Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps...
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    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.7 miles from Florida Keys Watersports
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
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    • Sauna
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    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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    1.0 miles from Florida Keys Watersports
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.7 miles from Florida Keys Watersports
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    About this property
    Alligator Reef is the Perfect getaway for large groups!  You can rent from 1 to 4 homes depending on the size of your group. The Pelican and Egret homes will offer you 2 homes, 5 bedrooms, and one pool.  The Pelican is a 3 bedroom 2 bath ocean front pool home which will sleep up to 8 people.  (Sofa...
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    Islamorada, Florida Keys
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    2.3 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. 'Beacon Reef 522' offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy with your choice to stay here....
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    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.3 miles from Florida Keys Watersports
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Washer
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    • Ocean Views
    • Cable/satellite TV
    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    COMMUNITY Anglers Reef is Islamorada’s premier gated, oceanfront community of 52 private, single-family homes, on Windley Key. Come stroll around its lushly landscaped grounds and “Bahamian conch cottages”, a unique and relaxing environment. Swim in the oceanfront resort-style pool which is kept...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.6 miles from Florida Keys Watersports
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Come and relax at our beautiful town home on...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.3 miles from Florida Keys Watersports
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Cable/satellite TV
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a great canal with easy access to the open ocean and the bay. We have plenty of room for your boat and all your toys. Bring or rent your boat, bike, paddleboards, jetskis or kayak. You have a world of fun in the sun awaiting. Located in one of the best neighborhoods in the keys!! Modern...
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    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    0.3 miles from Florida Keys Watersports
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • 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
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.3 miles from Florida Keys Watersports
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Washer
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    • Waterfront
    • Terrace
    • DVD Player
    • Patio
    • Balcony
    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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    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1.0 miles from Florida Keys Watersports
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
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    Location Information
    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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