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Islamorada Vacation Rentals

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    Travelers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 120 Rentals in Islamorada
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    Serenity Waterfront-Dock, View, Tiki Hut, spa/hot1 / 22
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    **Ready After Irma** Family Friendly Executive Bay Townhome with Beach & Pool1 / 25
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    **Ready After Irma** Modern Executive Bay Club Condo with Pool & Beach1 / 25
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Terrace
    • Wi-Fi
    • Grill
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 1, 2015
    Our townhouse was clean, spacious, & quiet. Lovely updated kitchen and laundry. The pool was delightful, and the beach & dock were very enjoyable as well. Very peaceful...
    Reviewed March 28, 2015
    I really enjoyed my stay! The place was great. I loved the layout. Very roomy. Enough space for everyone. The pool was great and even played a little tennis.
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    About this property
    This property has been inspected after hurricane Irma, is in good standing and is gladly accepting reservations at this time. We look forward to having you stay with us! *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    THIS IS IT! Magnificent Oceanfront Paradise!  WE ARE OPEN!!1 / 20
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Ocean Views
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2017
    The condo was great! Location was perfect for all the things we wanted to do. Nice quiet atmosphere, the tenants that live there are so nice. It was a perfect Florida Keys...
    Reviewed May 9, 2017
    This condo was perfect for our annual family vacation. The condo was very clean, well-equipped, and the online description was accurate. The owners were excellent to deal with...
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    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 4-6 people. Enjoy the tennis courts, large pool on the ocean, beach-side BBQ grills. Relax, dine and drink under one of the tiki huts or visit one of the many water-front restaurants and bars nearby....
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury 3 BR condo, boatslip, easy accces to ocean1 / 19
    (5)Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 28, 2017
    We thoroughly enjoyed our stay in this beautiful, luxurious condo. It's roomy and clean and has all the amenities you could possibly want. I only wish we could've stayed longer...
    Reviewed November 24, 2016
    very neat and clean. Great location and views. Easy access to all of the Keys. Spacious nice size kitchen for cooking a meal if you feel like it. Nice location, because it's far...
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    About this property
    Luxurious end unit in Bay Harbour with a boat slip. Upon entering the unit you are greeted with the tranquil views of the harbor and ocean. Enjoy the ocean breeze from the large screen porch. Beautiful Bay Harbour gated condo community on lower Matecumbe, mm 74 1/2. Enjoy the sunrise or sunset...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    Oceanfront 2 Bedroom/2 Bathroom Well Maintained Condo with Large Balcony1 / 14
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 2017
    This was a excellent place for our 30th wedding anniversary week. The owner was exceptional and had everything in the unit we could possibly need. Very helpful on suggestions...
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    About this property
    Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium complex with heated out door pool, gym, plenty of parking, secured entrances, elevator, and quiet. My condo is kept meticulously with attention to detail. Linens, towels and pool towels are included in the...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Islamorada Waterfront Paradise 21 / 29
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2016
    House was nice - except we did not feel comfortable - could not feel at ease - felt like we were being watched - paid a lot of money
    Reviewed April 22, 2015
    My husband and I just returned from Casa Rio. The home was clean and comfortable and quaint. The outdoor area was beautiful, charming and relaxing. We had access to bicycles...
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    About this property
    iF YOUR PLANS CALL FOR LESS THAN A MONTH, PLEASE CONTACT ME. i MAY BE ABLE TO HELP. ***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY*** Please contact us for all of our rates! For shorter stays...make sure you have a minimum of 28 days entered in your contact form!...
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    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • Air Conditioning
    • DVD Player
    • Grill
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has been inspected after hurricane Irma, is in good standing and is gladly accepting reservations at this time. We look forward to having you stay with us! *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury condo overlooking harbor with ocean view1 / 20
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Washer
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 2, 2017
    This condo is beautiful, clean and has great amenities (swimming pool, hot tub, tennis court and gym). Everything in the condo is first class with excellent quality of...
    Reviewed January 2, 2017
    This condo was gorgeous and well stocked. They kept a collection of brochures for all the activities around the area in the condo. We loved swimming in the pool and fishing in...
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    About this property
    This premier luxury home is situated in a very quiet and peaceful gated community. All the rooms are very spacious with quality furnishings. A large double wide lanai with breathtaking views will make your getaway in the Keys. For your enjoyment it comes with private boat dockage, covered parking,...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 2, 2016
    We loved our stay at Ocean Harbour Apartments. After viewing photos on your website, we chose this based on the beautiful grounds and lovely accomodations. We could not have...
    Reviewed January 5, 2015
    This spacious condo is beautifully furnished and equipped. The gated community is very quiet and has a heated salt water pool. There is a nice spot to see the moon and...
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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 FL 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has been inspected after hurricane Irma, is in good standing and is gladly accepting reservations at this time. We look forward to having you stay with us! Welcome to your beach-front oasis on the bay side at mile marker 74 in Islamorada, the Sport Fishing Capital of the World. Dig...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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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    Islamorada, Florida Keys 33023
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Terrace
    • DVD Player
    • Grill
    • Sauna
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ****Recently updated paint, furniture and a Beauty Rest Mattress!!**** Looking to escape reality? Look no further! Spacious 1 bedroom/1 bathroom condo located in the newly renovated Summer Seas Condominiums. Sit back and relax at the pool, go swimming at the private beach. Feeling adventurous?...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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    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 33036
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 1 BDRM apartment located in Islamorada. Full kitchen and 1 full bath. Home is located on canal within 100 yards of the ocean. You will enjoy access to fully screened and heated pool. WiFi and cable TV included. Close proximity to shopping, restaurants and all the best the Keys have to...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Oceanfront End Unit, Spectacular Water Views, Pool, WiFi, Tennis1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Sauna
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 2016
    Beautiful ocean views! Nicely decorated and well-cared for condo. We hope to return next year. We had everything we needed and felt like we were at home, a lovely relaxing home.
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    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. For two couples or a family with 2 kids. The two new extra long twin beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new king bed, ocean view and private bath. 2nd bathroom in hallway. This...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF1 / 25
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Waterfront
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    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 33036
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Oceanfront Anglers Reef Islamorada Florida Keys1 / 14
    (2)Average
    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 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 33036
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Islamorada Waterfront Paradise Getaway!1 / 28
    (31)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 14, 2017
    We spent a wonderful, spirit rejuvenating MONTH with Ewa and Peter at their beautiful home by a lagoon in Lower Matecumbe Key. At first we bustled about, kayaking from the dock...
    Reviewed March 1, 2016
    We had a delightful stay in this lovely property - by the water and with hammocks and a very peaceful setting. The room was well equipped and the owner were very helpful.
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    About this property
    Please contact us for all of our rates for different length of stays! For shorter stays...make sure you have a minimum of 28 days entered in your contact form! DO NOT BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you significant FlipKey booking...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Modern Keys Living with Bay Views! New from top to bottom!!! Newly remodeled and beautifully decorated 1st floor corner unit with a private entrance. Enjoy the mix of vintage and new furniture and the most comfortable sofas, beds, linens and more! This home is equipped with everything...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    **Ready After Irma** Fully Updated Modern Townhome with Pool, Beach & near1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 28, 2016
    Fantastic townhouse!! Came here to stay with a couple of friends and went fishing. It is right in the heart of Islamorada. You'll never run out of things to do, or places to eat...
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    About this property
    This property has been inspected after hurricane Irma, is in good standing and is gladly accepting reservations at this time. We look forward to having you stay with us! *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Islamorada Luxury Home Ocean & Bay Access1 / 14
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • 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 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Newly refinished  condo open water views very nice1 / 16
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Secure Parking
    • Internet Access
    • Air Conditioning
    • Waterfront
    Suitability
    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 condo in Futura Yacht Club. Pool, club house, Tennis, Marina with great fishing. Marker 88 restaurant is a short paddle board away. Private beach with sun set view. Perfect location near everything, restaurants, bars, shopping. Diving centers ,fishing, boat...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Perfect Getaway1 / 14
    (6)Very good
    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 pretty, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a pretty upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is additional tidy and modernly furnished....
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Grill
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 28 DAYS 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 cottage like...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxurious Condo-Exclusive Bay Harbour w/Boat Slip & Marina, Pool, Tennis courts1 / 15
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 25, 2015
    Great property! Very beautifully decorated. I loved the view, really enjoyed my stay! I look forward to staying there again soon!
    Reviewed January 19, 2015
    This condo is beautifully decorated and chock full of everything you need to make your stay just perfect. The condo and the complex are extremely well maintained and have the...
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    About this property
    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This lovely property is part of a gated,...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your awe moment begins as you drive through the gates of the Moja Draga Estate, located on a beautiful 2 acre parcel of prime ocean front property in the village of Islamorada. Moja Draga is where your vacation dreams begin. Your island vacation home is well appointed with all that you need for a...
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    Islamorada, Florida Keys 33070
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Private Yard
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    Pet friendly
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    Smoking allowed
    About this property
    Live your tropical dream at this palatial oceanfront estate. Located near mile marker 89, on Islamorada's Millionaires' Row, this 4 bedroom / 6 bath home comes with just about every convenience you can imagine, as well as some you probably haven't even considered. Enjoy a swim in the pool that...
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    Islamorada, Florida Keys 33070
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    Luxurious Anglers Reef with Boat Slip, Pool, Ocean1 / 29
    (26)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Patio
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    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 33036
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    **Fall Promo** Gorgeous Keys Waterfront Home with Private Dock & Ramp1 / 24
    (4)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    Reviewed October 27, 2015
    This house was absolutely great! I loved that it had a dock and I was able to bring my boat with me instead of having to leave it at a marina. I stayed here for a week with a...
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** This water front home is located oceanside in the tropical Lower Matecumbe key, Islamorada, mile marker 73 (The Sport Fishing Capital of the World). It features a 15' wood dock and 12’ wide ramp, so you can bring your own boat and...
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    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Islamorada Luxury Waterfront Condo with Boat Slip1 / 21
    (13)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 8, 2017
    Very comfortable condo. Enjoyed a week of R&R. Very quiet place. Great pool. Deanna, the owner, was very helpful giving us help in launching our boat, storing our trailer...
    Reviewed May 1, 2017
    Excellent locationt, accommodations where great, all you need to bring is yourself and clothes. Deanna the owner was prompt in answering any questions regarding the property...
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    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Corner lot, Clear and deep waterways, 3 bedrms, 3 bath, sleeps 8+ Granit Tops This home is located in a prime neighborhood with 150lf of seawall for all your water toys. 3 bedrooms, 3 full bath ,1 king, 2 queens and bunkbeds, Laundry room, Wet bar, Library/Sitting room, Living /Family room and...
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    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    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 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you have your sights set on the ideal spot to spend your next tropical getaway, then jump on the chance to book your stay at this dog-friendly, oceanfront Islamorada home on a one-acre lot. Boasting a private stretch of white sand beach, a private pool, hot tub, and water toys like kayaks and...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Patio
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 1 Month Enjoy the magnificent ocean views of this wonderful condominium complex. You'll love the newly completed renovations. The kitchen has been totally remodeled with all new cabinets and appliances. The living room furniture is brand new and there's a big flat screen TV...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    FLORIDA KEYS OASIS - The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 32
    (4)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 12, 2017
    The property manager was super helpful and walked us through the entire house showing us all the nooks and crannies. I must say I've never had someone take close to 45-an hr to...
    Reviewed February 12, 2017
    On our recent family trip to the keys, we were lucky enough to find this amazing home. We stayed for one week and wish we had stayed a month!The house is 6 stars and the hosts...
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    About this property
    ***7 day minimum rental - notwithstanding anything in the rates page the MINIMUM rental is 7 days ****This custom built 5 bedroom house has been immaculately taken care of and has a proper size elevator and is fully wheel chair accessible. Enjoy your stay in Sereni-key looking out to an endless...
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    Islamorada, Florida Keys 33036
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Property description Framed by mangroves and the Atlantic Ocean this exquisite Key West style 2 bedroom, 2.5 bathroom home, is located in the quiet oceanfront private community of Anglers Reef -one of the best kept secrets in the Keys. Florida State Licensed Single Family Vacation Rental Dwelling...
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    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    **Fall Promo** Ocean Front Keys Home with Private Beach - Great for Kite1 / 25
    (2)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 6, 2016
    Had a wonderful time beach just out front and did a lot "beaching". Close to a nice supermarket and rental places. Will definitely be back! Thanks for a great get away!
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    About this property
    Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo, on mile marker 74). Welcome to our little slice of paradise in the Florida Keys! Come and relax at our beautiful ocean front home with breathtaking, panoramic views of the Atlantic ocean. This spit...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 29 DAYS - Available this winter! Very comfortable 50ft dock, wide canal, home located close to Tavernier Creek Channel with easy access to the Gulf and Atlantic. Great fishing, kayaking and diving. Concrete dock, fish cleaning station . 1.5 mile north of the world famous Holiday...
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    Location Information
    Islamorada, Florida Keys 33070
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Highend remodeled and luxuriously furnished bay view condo in the gated community of Futura Yacht Club. 2 bedroom 2 full bath Condo with a open den that can be closed off as a third room (queen size murphy bed). Flat screen tv in every room with cable and wifi. Gorgeous modern kitchen with eat in...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    PALMS 4171 / 25
    (1)Excellent
    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 33036
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    PALMS 3091 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Terrace
    • Internet Access
    • Balcony
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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 Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen...
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    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 BEDROOM CONDO MARINA AND DOCKAGE1 / 39
    (14)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Balcony
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    • Outdoor Dining Area
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 13, 2017
    Plantation Key in Islamorada and the Futura Yacht Club is great. Lots do do without having to leave Islamorada. If you love snorkeling, diving, swimming, fishing, kayaking...
    Reviewed May 1, 2017
    Location was perfect for exploring the middle Keys. Pool was awesome. We loved the grill out by the Gulf of Mexico, it made for a memorable dinner/ sunset.
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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 33070
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #407' is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. You...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    VILLA RIOLO1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2014
    Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.
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    About this property
    Minimum Rental: 28 Days 'Villa Riolo' is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity to...
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    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    SUNSHINE PLACE1 / 23
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    Reviewed May 13, 2016
    Having been acquainted with the area and having been, physically, all 'round the property, occasionally, but never in it - it was a shocking and wonderful surprise that this...
    Reviewed February 8, 2016
    A surprisingly tranquil place bearing in mind that it is positioned in its own grounds between two neighbouring resorts. The rental accomodation is the ground floor of a two...
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    Minimum Rental: 7 Days '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 people who...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    BEACON REEF 3101 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
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    • Cable/satellite TV
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Minimum Rental: 28 Days 'Beacon Reef 310' is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your own...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    • Balcony
    • Patio
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days 'The Palms #402' is a beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony. Watch the fishing boats...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Ocean Views
    • Washer
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    • DVD Player
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa (Half Duplex), three bedrooms / two bathrooms plus a loft and a crow's nest area with great views. Relax and enjoy a peaceful getaway in beautiful Islamorada, Florida. This unique home is nestled on a bay overlooking the ocean. There is approximately 50' of deep-water dockage with access to...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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