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Villas and Holiday Rentals in Islamorada, FL

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    All 143 Rentals in Islamorada
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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
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    €774
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    1 / 30
    5 of 5 stars (18) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
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    €273
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    1 / 35
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    4 of 5 stars (6) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
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    1 / 29
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dryer
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    • Private Fishing...
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    • Shared Outdoor Pool...
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    • Pets allowed
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    • x
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    About this property
    Thank you for considering Our home in the Florida Keys!... Our slice of Paradise! Stay at a Luxury Townhome at Executive Bay Club (Islamorada , Florida ) The Executive Bay Club is located in Islamorada which is best known for it's crystal blue water where you can enjoy sport fishing, snorkeling,... View all property information
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    Islamorada, Florida Keys 33036
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    €455
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    1 / 22
    4.5 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    **We do not use the optional calendar feature on this listing. ** ***For holiday weeks, lobster opening week, and lobster mini season week rates will be higher.*** This is a very popular rental, so book your preferred week well in advance of peak season! I reply to EVERY inquiry. If you do not... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 23 April 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...
    5 of 5 stars Reviewed 14 April 2015
    We had a wonderful time at this waterfront paradise. Waking up in the morning to a beautiful view of the waterway outside the window of our bedroom. Not to mention enjoying the...
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    €3,633
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    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Balcony
    • Grill
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal.... View all property information
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    Islamorada, Florida Keys 33036
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    €5,464
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    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Relax and enjoy a peaceful getaway in beautiful Islamorada, Florida. This unique home is nestled on a bay overlooking the ocean. We are located on Lower Matecumbe Key just a few miles south of the hustle and bustle of downtown Islamorada. This is a spacious three bedroom with vaulted ceilings, a... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 19 November 2014
    We stayed at Captains Cove again for our annual fishing weekend. Cindy, the new owner, has made several updates to the house, deck and dock which enhanced the property since our...
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    1 / 19
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Vacation in Paradise!!... you will love this fun filled, relaxing townhouse in the beautiful Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 12 April 2015
    The owners were amazing to work with and very quick to answer any questions. The condo was beautiful and very well stocked with anything you would need for a vacation in the Keys...
    5 of 5 stars Reviewed 7 March 2015
    The Daniels unit in Executive Bay Club is great. Very clean and modern up to date. People were very friendly and helpful nice events in clubhouse. Large rooms upstairs and...
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    €1,730
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    1 / 15
    5 of 5 stars (1) Excellent
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    • Gym
    • Hot Tub
    • Satellite TV
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. 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... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    €1,548
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    1 / 19
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Ocean Views
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • x
    About this property
    BEAUTIFUL NEWLY REMODELED 3 BEDROOM, 2 FULL BATHROOM VACATION RENTAL IS LOCATED IN THE EXECUTIVE BAY CLUB. BREATHTAKING BAY VIEW FROM YOUR OWN BACK YARD! UNIT HAS BRAND NEW CUTOME KITCHEN CABINETS WITH GRANITE COUNTER TOPS. ALL STAINLESS STEEL APPLIANCES, DOUBLE DOOR REFRIGERATOR, DISHWASHER,... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 24 April 2015
    We really enjoyed our stay here. We stayed with my husband and I and 3 kids ages 8,6 and 2. It was perfect. We spent a lot of time at the pool which was about 20 steps from the...
    5 of 5 stars Reviewed 24 February 2015
    The place was beautifully decorated and in excellent condition. From the patio you had an excellent ocean view that was a short walk to a small beach. My teens has a blast and...
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    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 17 November 2014
    my husband and 2 friends stayed in this unit for 4 days and 3 nights. they found the condo to be clean, plenty of space and conveniently located. they would definitely stay...
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    1 / 29
    5 of 5 stars (22) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 20 August 2014
    We fell in love with the villa the minute we walked in through the door. Everything was immaculate and extremely welcoming. The owner had thought about everything and the box of...
    5 of 5 stars Reviewed 30 June 2014
    This was the perfect place for a relaxing vacation with my extended family. The location was great, and close to all Islamorada has to offer. The pool was so nice, overlooking the...
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    €127
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    1 / 11
    3 of 5 stars (1) Average
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Ocean Views
    • Sauna
    • Shared Outdoor Pool...
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on sea. Once this salt air gets in you you will never want... View all property information
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    Islamorada, Florida Keys 33070
    3 of 5 stars Reviewed 11 April 2015
    I spent a week at Sea Gulls with my 18 year old daughter. The unit was well equipped and clean. The pool and tennis courts were nice. The view was adequate. To the left, a...
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    €209
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    1 / 4
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Grill
    • Hot Tub
    • Internet Access
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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... View all property information
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    Islamorada, Florida Keys 33036
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    €947
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    1 / 19
    5 of 5 stars (3) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights You can have it all – 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 treasure... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 13 March 2015
    If your looking for the whole package in one this is the place. View, comfortable, privacy and location. Best place I've stayed in the keys, hands down!
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    €4,234
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    1 / 9
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Gym
    • Private Fishing...
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Available: November: 4900 January through May: $5000 single month, three or more months $4800. PLEASE DO NOT SUBMIT A REQUEST FOR A PERIOD LESS THAN ONE FULL MONTH KINDLY NOTE: MONTHLY RENTAL. To maintain the beauty of Beacon Reef, rental contracts must be for no less than a month. This... View all property information
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    Islamorada, Florida Keys 33036
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    €911
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    1 / 9
    2 Bedrooms / 4 Bathrooms / Sleeps 4
    traveller have booked this property
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    • Air Conditioning
    • Balcony
    • Grill
    • Ocean Views
    • Shared Outdoor Pool...
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    This oceanfront condo in Islamorada Florida (Keys) is located at mile marker 90. It is the best ocean view from everyroom and is on the 4th floor. IT IS A ONE WEEK MINIMUM AND 4 PERSON MAXIMUM BY LICENSE. ..It has all tiled floors, newly painted, new AC, and has all the conveniences of home.... View all property information
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    Islamorada, Florida Keys 33070
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    €4,553
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    1 / 10
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Imagine waking to the beauty of a sunrise brimming over the aqua seas. Linger in your master suite and watch the ocean shift through a prism of aqua, blues and emerald greens. Gentle breezes waft through this two bedroom, two bath condo with comfortable appointments and an elegant sea glass... View all property information
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    Islamorada, Florida Keys 33036
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    €228
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    1 / 7
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    traveller have booked this property
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This Coastal Conch Style Cottage has been recently updated to accommodate vacation renters and their families. The cottage has all new furnishings and accessories that offers a 'home away from home' feel. The Coastal style conch cottage is located in the gated community, ocean front resort... View all property information
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    Islamorada, Florida Keys 33040
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    €455
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    1 / 38
    5 of 5 stars (23) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (23) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email VenetianTropics@aol.com for the application.... View all property information
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    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed 24 March 2015
    The home is luxurious. It has all the amenities needed for a trip to the Keys. This is the third time I have rented the home and there have been some nice improvements made to the...
    5 of 5 stars Reviewed 19 May 2013
    This home was the perfect location for our spring break vacation. It was so central to many activities on the keys and so many wonderful restaurants. The home is very nice, a...
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    €228
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    1 / 20
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
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    • Balcony
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
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    €1,594
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    1 / 33
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    traveller have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen, snorkel in the backyard!!!! Seven Flat Screens and entire house wired for sound.... View all property information
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    Islamorada, Florida Keys 33036
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    €2,527
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    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    This property is a single family home with a boat dock included in the price. Not a condo. Note: we only offer 7 day minimum stays with 4PM Saturday check ins and 10 AM checkouts. Maximum number of guests is 5. No pets, No smoking and maximum guests is strictly enforced by onsite security. Rates... View all property information
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    Islamorada, Florida Keys 33036
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    €254
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    1 / 25
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    traveller have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    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... View all property information
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    Islamorada, Florida Keys 33036
    From
    €2,732
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    1 / 27
    Studio / Sleeps 4
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Washer
    • Waterfront
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this... View all property information
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    Islamorada, Florida Keys 33036
    From
    €163
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    1 / 4
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Balcony
    • Grill
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Enter through a private garden with a tropical atmosphere to a quiet and secluded room with a queen size bed and a private bath. The room is completely private and features a coffee maker, microwave, refrigerator, TV and free WiFi. Full breakfast. LOCATED IN A QUIET,SECLUDED , TROPICAL SETTING... View all property information
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    Islamorada, Florida Keys 33136
    From
    €888
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    1 / 20
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Two Acre Ocean Front Estate in the heart of Islamorada. Over 200 feet of ocean front with an ocean front pool with two sides in the Atlantic. A large flat beach area with a large patio at the ocean's edge. The estate has two villas, both have a full kitchen, living room, pull out sofas and... View all property information
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    Islamorada, Florida Keys 33036
    From
    €109
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
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    • Internet Access
    • Private Fishing...
    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
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    About this property
    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;... View all property information
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    Islamorada, Florida Keys 33036
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    €117
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    1 Bedroom / 1 Bathroom / Sleeps 2
    traveller have booked this property
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    • Pets allowed
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    • x
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    • ?
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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... View all property information
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    Islamorada, Florida Keys 33036
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    1 / 47
    3 of 5 stars (3) Average
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Balcony
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    • Gym
    • Satellite TV
    • Sauna
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    About this property
    Complex Amenities - MM 88.5 - Building has five floors - Large swimming pool & children's pool - Exercise room with sauna - Laundry room on each floor - Billiard and Ping-Pong room - Adult party lounge - Cookout facilities - Direct access to Florida Bay and then ocean - Minutes from Islamorada,... View all property information
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    Location Information
    Islamorada, Florida Keys 34747
    2 of 5 stars Reviewed 22 August 2013
    In addition to my wife's comments there is another thing a prospective renter must take into consideration: the lease agreement states that any disputes with the rental agent be...
    2 of 5 stars Reviewed 13 August 2013
    My husband and I recently rented this condo for a 3-night dive trip with our 2 boys, ages 17 and 19. While the condo itself was clean, the building was old and the parking lot was...
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    1 Bedroom / 2 Bathrooms / Sleeps 2
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    • Air Conditioning
    • Grill
    • Internet Access
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    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • ?
    • ?
    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... View all property information
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    Islamorada, Florida Keys 33036
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    €81
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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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,... View all property information
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    Islamorada, Florida Keys 33036
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    €390
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    1 / 21
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    About this property
    Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new... View all property information
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    Islamorada, Florida Keys 33036
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    €1,548
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    1 / 25
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
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    • Dryer
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    • Safe
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • x
    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... View all property information
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    Islamorada, Florida Keys 33023
    From
    €325
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    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    ower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up to 6 people - rent one or all... View all property information
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    Islamorada, Florida Keys
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    €1,366
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    1 / 36
    4 of 5 stars (16) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (16) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world... View all property information
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    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed 11 January 2014
    Location, location, location; this home was a great getaway, and beautifully landscaped (but not manicured) with older Australian pines, sea grape, palms and silver buttonwood...
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    1 / 11
    5 of 5 stars (1) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
    About this property
    ****This house cannot rent for less than 28 days, per County Ordinance**** Latitude: Freedom of thought or action. No word could better described this Keys Vacation Home. Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool. Latitude boasts 2 master suits and... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 16 June 2013
    Our extended family of 8 had a wonderful week at Latitude. The house is modern and immaculate. There was plenty of space and privacy for everyone. We had a great time watching...
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    5 of 5 stars (3) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    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... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 7 February 2015
    This condo has more than you would expect in a condo. It has every utensil, cookware, storage containers appliances both small and large you could ever need. Unlike most condo...
    5 of 5 stars Reviewed 3 September 2014
    Looked far and wide for a place in the keys that was on one level for my mom that uses a walker. Finally found the one! The owner is very helpful and communicative and worked...
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    €1,821
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    1 / 24
    4.5 of 5 stars (6) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (6) Make Enquiry
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    • Dishwasher
    • Grill
    • Internet Access
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    • ?
    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. VACATION RENTAL LICENSE: VR-039 CLICK HERE to view photos on a mobile device.... View all property information
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    Islamorada, Florida Keys 33036
    From
    €18,121
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    1 / 15
    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    ****This house cannot rent for less than 28 days, per County Ordinance**** Breathtaking Sunset's, Breathtaking Home. Pineapple Plantation is an unbelievable gated, New Bay Front home. It is perfectly located a Mile Marker 89, Islamorada. Boasting 5 Bedroom Suite's, Gourmet kitchen with an ocean... View all property information
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    Islamorada, Florida Keys 33036
    From
    €2,277
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    1 / 19
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 28 May 2013
    The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough for...
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    €1,138
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    1 / 27
    4.5 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights (Saturday to Saturday) BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open... View all property information
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    Islamorada, Florida Keys 33070
    4 of 5 stars Reviewed 1 June 2014
    Having stayed in other properties at Futura Yacht Club over the years, I can honestly say that this was by far the nicest. The kitchen had been recently renovated with new white...
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    1 / 27
    5 of 5 stars (4) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights Lower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €5,919
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    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €1,912
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    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of the Atlantic... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €2,277
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    1 / 31
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 14 January 2015
    Little Bay was a perfect property for us! The setting is idyllic and classic keys - Huge backyard on the Bay with excellent dock area, hammocks and view of the bay. Covered...
    5 of 5 stars Reviewed 2 July 2013
    We have rented the upper duplex of Little Bay in April for the last few years. it is a beautiful property in a perfect setting. The grounds are kept immaculately and the area by...
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    €325
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    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Venetian Shores 3/3 home with deep water boat slip, gorgeous custom pool with integrated hot tub and built-in seating. This beautifully updated tri-level home offers a 2/2 upstairs with soaring ceilings, wood floors and a wide porch off the living room overlooking the pool and a wide turn in the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 24 March 2015
    Lovely Home, very spacious, clean, everything you need..... the Owners had. We even saw a Mother Manatee with their baby swimming upto our boat slip in the back. This was our...
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    €728
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    1 / 30
    4.5 of 5 stars (9) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    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, basketball and... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    3 of 5 stars Reviewed 4 March 2014
    This was a nice rental. There seems to have been a nice soft update done not to long ago, and it appeared that some features were still being upgraded. The building is clean...
    5 of 5 stars Reviewed 13 January 2012
    The condo was great! It was clean and located in a great place in the Keys. There were many excellent restaurants in the area when you wanted to go out, and a full kitchen when...
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    €97
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    4.5 of 5 stars (11) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Escape from the world in this beautiful island paradise.Plenty of room to spread out in a two bedroom condo. Relax by the heated pool overlooking the turqoise bay; fish from the dock, snorkel in the protected cove. Kids can play in the game room or playground. Enjoy the clear, turquoise waters,... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 10 July 2014
    Stayed here the last week in June with my wife, two kids and granddaughter. Room was clean and well laid out but a little bit cramped for the number of people. Closet space was...
    5 of 5 stars Reviewed 26 May 2014
    The condo was nicer and larger than we expected. It had everything we needed plus a few surprises: beach chairs and a float, very comfortable beds, and quiet neighbors. Also...
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    €1,912
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    1 / 16
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month This exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure to look at the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036