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Islamorada Vacation Rentals

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    Travelers to Islamorada are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    4 of 5 bubbles
    16 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    5 of 5 bubbles
    1 Review
    2 Bedrooms, Sleeps 6Quick View
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    5 of 5 bubbles
    4 Reviews
    1 Bedroom, Sleeps 4Quick View
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    4.5 of 5 bubbles
    13 Reviews
    1 Bedroom, Sleeps 3Quick View
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    • Grill
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Patio
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed June 6, 2016
    Wonderful vacation nice, relaxing. I would definitely return. Charlie was very informative on where to go to eat. Locals were very nice too.
    Very good of 5 bubbles
    Reviewed October 16, 2015
    What a great little spot! Was quiet and very peaceful. Clean and cozy! Had everything we needed. Will be back to Stay again soon! :)
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    About this property
    Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes <BR>Wifi, boat dock, trailer parking, and all amenities are included also, <BR><BR>Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee...
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    Islamorada, Florida Keys 33037
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4.5 of 5 bubbles
    4 Reviews
    1 Bedroom, Sleeps 2Quick View
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    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Grill
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Average of 5 bubbles
    Reviewed December 18, 2016
    Appealing features: Convenient location. The grounds were beautiful, with a little waterfall, trees, plants and interesting art around little sitting areas in the courtyard...
    Excellent of 5 bubbles
    Reviewed May 26, 2016
    I recommend this B&B to anyone who just wants a beautiful property to relax and enjoy the company of your significant other. The staff is very attentive and accommodating and...
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    About this property
    This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET...
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    Islamorada, Florida Keys 33036
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 of 5 bubbles
    2 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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...
    Excellent of 5 bubbles
    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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    5 of 5 bubbles
    4 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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...
    Excellent of 5 bubbles
    Reviewed July 22, 2016
    This place was in a great location, beautiful view, nicely furnished, perfect in every way. Would definitely stay next time I'm in the area!
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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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    2 Bedrooms, Sleeps 6Quick View
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    • 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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    5 of 5 bubbles
    3 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Ocean Views
    • Washer
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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...
    Excellent of 5 bubbles
    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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    5 of 5 bubbles
    1 Review
    1 Bedroom, Sleeps 2Quick View
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    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • DVD Player
    • Secure Parking
    • Wi-Fi
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 2 weeks ago
    A beautiful place in a quiet neighborhood. Thorn is a wonderful host and the breakfast was delicious!
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    About this property
    A small stand alone room in the corner of the garden. Features a/c, coffee maker, free WiFi, grill on premises, heat, microwave, refrigerator, shared bathroom with one other couple, TV and includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO FISHING, DIVING,...
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    Islamorada, Florida Keys 33036
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 of 5 bubbles
    7 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Wi-Fi
    • Satellite TV
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed June 14, 2016
    This was our first trip to Florida, it was agreed that we would leave Orlando and the parks for a few years as our children are still quite young (4 and 1). We did extensive...
    Excellent of 5 bubbles
    Reviewed January 18, 2016
    We had very nice time staying in Ana's townhouse in Islamorada. It is nicely decorated, well equipped, comfortable and spotlessly clean. There is more than enough room for a...
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    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    1 Review
    2 Bedrooms, Sleeps 6Quick View
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    • DVD Player
    • Patio
    • Waterfront
    • Grill
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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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    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rental amount includes all fees boat dock fee.. This newly renovated modern 4th floor condo in a private gated community has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened in Lanai, 2 lighted tennis courts, and...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 of 5 bubbles
    4 Reviews
    4 Bedrooms, Sleeps 8Quick View
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees.  Mile Marker 76, Bayside. Home has 2 bedrooms & 2 bathrooms upstairs, and a separate 2 bedroom, 2 bathroom apartment downstairs (3rd floor inaccessible to...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, Sleeps 3Quick View
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    • Patio
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Housekeeping Included
    • Grill
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Moroccan room is a fabulous honeymoon destination with king size canopy bed. Room features a/c, coffee maker, heat, microwave, refrigerator, TV, WiFi. Enormous bathroom with sunken tub and terrycloth robes to lounge in includes full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET...
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    Islamorada, Florida Keys 33036
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4.5 of 5 bubbles
    5 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Waterfront
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Average of 5 bubbles
    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 😕
    Excellent of 5 bubbles
    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, Sleeps 4Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the spectacular view of the Florida Bay from this beautiful townhome. 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 property. Make your self at home in our home away from...
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    Location Information
    Islamorada, Florida Keys 33070
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    • Ocean Views
    • Grill
    • DVD Player
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    10 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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...
    Very good of 5 bubbles
    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
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 bedroom 2.5 bath luxury condo at MM 74.5 Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and free Wi-Fi at community clubhouse (this unit does not have Wi-Fi inside the condo) . The condo boasts some amazing views of the Clear Blue...
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    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    8 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed March 25, 2015
    We had a terrific time at 137 Lessara this February. The wildlife (birds, fish, manatee) viewing was incredible, the weather great, and the house was fantastic- especially the...
    Very good of 5 bubbles
    Reviewed June 5, 2014
    This house had more than enough of everything needed away from home.The decks on both floors were great for relaxing,visiting, grilling and tanning.Plenty of space our three...
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    About this property
    Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two...
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    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    8 Reviews
    5 Bedrooms, Sleeps 10Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed January 12, 2015
    We seven people (3 couples and one single) stayed here for one week. This big house is located right on the Atlantic Ocean, but it has no beech. It has a great wraparound porch...
    Very good of 5 bubbles
    Reviewed August 12, 2014
    The home that we stayed at was incredible! The accommodations, the view, the boat dock space was all great. It was fast in and out to the Atlantic Ocean to be able to scuba...
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    About this property
    Amazing ocean views can be enjoyed from this beautiful stilt home with separate mother- in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile...
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    Islamorada, Florida Keys 33036
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    "The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the...
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    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer and living area that opens up onto a large...
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    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 5Quick View
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    • Air Conditioning
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    4.5 of 5 bubbles
    8 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed April 1, 2016
    Three of us stayed for a week in March 2016. Unfortunately two more friends had to pull out due to illness, so we had a surplus of rooms. The house is not the most modern of...
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    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. Near the house is the small Anne's Beach. There are nature trails, board walks to...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    10 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Internet Access
    • Waterfront
    • Hot Tub
    • Washer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed January 16, 2017
    Extremely clean and comfortable condo in a great location. View of sunrise from Master Bed! Beautiful large balcony to enjoy breakfast, drinks. :) Lots of extras- pool, use...
    Excellent of 5 bubbles
    Reviewed November 3, 2016
    This place was absolutely terrific. The amenities exceeded the list and our expectations. We also met some great residents and enjoyed our time thoroughly. Also, Islamorada...
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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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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Washer
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 of 5 bubbles
    1 Review
    2 Bedrooms, Sleeps 4Quick View
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    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Sauna
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 of 5 bubbles
    3 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    • Air Conditioning
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    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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!
    Excellent of 5 bubbles
    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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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 of 5 bubbles
    24 Reviews
    2 Bedrooms, Sleeps 5Quick View
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    • Patio
    • Grill
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 1 week ago
    Great place to setup home base in the Keys. The home had everything we needed, including a fully stocked kitchen for cooking our fresh catch. Nice, quiet community with many...
    Excellent of 5 bubbles
    Reviewed September 13, 2016
    I highly recommend Islamorada and this was a great place to stay. The house was very clean and everything is right there so you can relax and enjoy your vacation. The...
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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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    4.5 of 5 bubbles
    3 Reviews
    3 Bedrooms, Sleeps 8Quick 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
    Very good of 5 bubbles
    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...
    Excellent of 5 bubbles
    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
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, Sleeps 3Quick View
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    • DVD Player
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Outdoor Dining Area
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Malaysian room is poolside in a tropical atmosphere facing a beautiful waterfall. Features a mini kitchen with blender, coffee maker, microwave, refrigerator and toaster oven. A/C, heat, TV and WiFi. Includes a full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO...
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    Islamorada, Florida Keys 33036
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, Sleeps 6Quick View
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    • Waterfront
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Balcony
    • Washer
    • Air Conditioning
    Suitability
    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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    4 Bedrooms, Sleeps 11Quick View
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    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Heated)
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home features 4 bedrooms, 2 baths, pool and bar. This home can comfortably accommodate 8-10 people with room to spare. Alluring turquoise ocean and beachfront views. The onsite boat parking provided tremendous privacy and space for you and all of your guest. A private pool and grill that...
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    Location Information
    Islamorada, Florida Keys 33070
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    5 Bedrooms, Sleeps 10Quick View
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 33036
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 10Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Terrace
    • Satellite TV
    • Parking
    • Internet Access
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days "Lyons Landing" is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home. 3 bedrooms and two baths on the upper level plus a bedroom and...
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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 of 5 bubbles
    3 Reviews
    5 Bedrooms, Sleeps 10Quick View
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    • Patio
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Secure Parking
    • Grill
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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...
    Excellent of 5 bubbles
    Reviewed August 15, 2016
    This house was a beautiful place to stay with large common areas for gathering our big group, but with private bedrooms and bathrooms. All the ocean toys we needed. We had a...
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    About this property
    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 oasis over a full size, heated lap pool. Lay down in the shade on the soft grass bordering the pool and...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 10Quick View
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    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    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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    2 Bedrooms, Sleeps 6Quick 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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    5 of 5 bubbles
    4 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Washer
    • Satellite TV
    • Patio
    • Secure Parking
    • Internet Access
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 3 weeks ago
    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...
    Excellent of 5 bubbles
    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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    1 Bedroom, Sleeps 4Quick View
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    • Private Yard
    • Air Conditioning
    • 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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    5 of 5 bubbles
    3 Reviews
    2 Bedrooms, Sleeps 8Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed November 10, 2016
    Loved the home. Everything that was advertised was available and easy to use and find. Nice pool, access to the beach, and close to tons of activities. We were here for a family...
    Excellent of 5 bubbles
    Reviewed April 20, 2016
    I highly recommend this vacation rental! Very clean the pictures online are exactly what you see when you enter this beautiful home. It’s safe, convenient, well decorated...
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 18Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people. The Upper Duplex & The...
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    Islamorada, Florida Keys 33036
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 18
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    2 Bedrooms, Sleeps 6Quick View
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    • Secure Parking
    • Satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This beautiful 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 33036
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 of 5 bubbles
    4 Reviews
    3 Bedrooms, Sleeps 7Quick View
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    • Grill
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 of 5 bubbles
    2 Reviews
    4 Bedrooms, Sleeps 10Quick View
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    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    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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    5 of 5 bubbles
    6 Reviews
    1 Bedroom, Sleeps 3Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    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...
    Excellent of 5 bubbles
    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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    About this property
    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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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    • 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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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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