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Weekend Getaways in Islamorada - Vacation Rentals

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    1 / 22
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 stars (11) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3
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    1 / 9
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2
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    1 / 19
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Wi-Fi
    • Shared Tennis Court
    • Watersports Nearby
    • Grill
    • Satellite TV
    • Air Conditioning
    • Dryer
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    No short term stays (under 28 days) 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... View all property information
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    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed June 14, 2015
    This is a beautiful apartment. Unfortunately we were expecting to be right on the bay, as per the pictures, and when we found the apartment in the middle of the urbanisation, it...
    5 of 5 stars Reviewed April 12, 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...
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    $85
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    1 Bedroom, 1 Bathroom, Sleeps 2
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    • Refrigerator
    • Grill
    • Balcony
    • Air Conditioning
    • DVD Player
    • Private Fishing...
    • TV
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
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    • Elder access
    • x
    About this property
    The Hippie Home was Built with Love in the Sunshine of the Spirit. Nestled in Islamorada, the Sportfishing Capital of the World. The Neighborhood is Quiet and Pet Friendly with a Private Beach and Tiki Hut. Close to Restaurants, Shopping, Recreation, Fishing Charters, Scuba Diving, and Snorkeling.... View all property information
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    Islamorada, Florida Keys 33036
    From
    $220
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    2 Bedrooms, 2 Bathrooms, Sleeps 10
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    • Air Conditioning
    • Linens Provided
    • Wi-Fi
    • Secure Parking
    • Towels Provided
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Make yourself at home in your own private paradise in the Fabulous Florida Keys! The exclusive Executive Bay Club is a gated community with 24 hour security situated waterfront on the Florida Bay in Islamorada, just an hour from the hussle and bustle of Miami, yet a world away. Enjoy five-star... View all property information
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    Islamorada, Florida Keys 33036
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    $1,700
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
    Overview Make Inquiry
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    • Private Fishing...
    • Children's Pool
    • Water Views
    • Waterfront
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Islamorada, Florida Keys 33023
    From
    $229
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    1 Bedroom, 1 Bathroom, Sleeps 3
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    • DVD Player
    • Housekeeping...
    • TV
    • Wi-Fi
    • Shared Outdoor Pool...
    • Watersports Nearby
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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 YET... View all property information
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    Islamorada, Florida Keys 33036
    From
    $4,000
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    4 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Water Views
    • Hot Tub
    • Stereo System
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This home is located minutes from Snake Creek Channel and is minutes from ocean and bay access. 1.5 mile north of the world famous Holiday Isle Tiki Bar and less than 2 hours away from Key West. If you enjoy fishing, snorkeling, diving this is the perfect for you . Located at Plantation Key Colony.... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    From
    $1,750
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    4 Bedrooms, 5 Bathrooms, Sleeps 10
    other traveler has booked this property
    Overview Make Inquiry
    Overview
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    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    • DVD Player
    • Water Views
    • Air Conditioning
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Location Information
    Islamorada, Florida Keys 33036
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    From
    $300
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    3 Bedrooms, 5 Bathrooms, Sleeps 8
    Overview Make Inquiry
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    • Watersports Nearby
    • Hot Tub
    • Air Conditioning
    • Water Views
    • Satellite TV
    • Ocean Views
    • Housekeeping...
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    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... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    $1,498
    / Week
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    1 / 9
    5 of 5 stars (1) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 4
    other traveler has booked this property
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    • Linens Provided
    • Ocean Views
    • Grill
    • Air Conditioning
    • Balcony
    • Parking
    • Wi-Fi
    • Elevator/Lift access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    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
    5 of 5 stars Reviewed August 14, 2015
    My husband and I spent a fantastic week at this beautiful condo! The pictures don't do it justice! The view is spectacular. The inside is clean and nicely decorated! The owner is...
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    $250
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    1 / 25
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Amenities & Details
    • Private Outdoor...
    • Gym
    • Deck
    • Air Conditioning
    • Waterfront
    • Washer
    • Internet Access
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 November 16, 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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    $140
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    1 / 15
    4 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4
    other travelers have booked this property
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    Amenities & Details
    • Sauna
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • TV
    • Watersports Nearby
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • 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
    5 of 5 stars Reviewed August 11, 2015
    My wife and I along with another couple spent a week at this condo. While an older development, it proved quite comfortable and convenient to all of the Islamarado restaraunts and...
    4 of 5 stars Reviewed June 4, 2015
    My husband and I stayed 10 days at this condo and loved it. It is clean, comfortable and fully equipped. We have already booked it for next spring. The beach is crushed coral...
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    From
    $2,800
    / Month
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    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Refrigerator
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Great location canal front on the ocean side of Lower Matecumbe Key. The home sits on a double lot giving lots of space. The home wraps around a large boat basin for ample dockage. At times we have kept three 26 to 28 ft center console fishing boats here. This is a perfect dock setting to work... View all property information
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    Islamorada, Florida Keys 33036
    From
    $1,700
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    1 / 19
    5 of 5 stars (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
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    Overview Reviews (3)
    Amenities & Details
    • Shared Tennis Court
    • Watersports Nearby
    • Air Conditioning
    • TV
    • Water Views
    • Stereo System
    • Ocean Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    BEAUTIFUL NEWLY REMODELED (Available for 28 day rental) 3 BEDROOM, 2 FULL BATHROOM VACATION RENTAL IS LOCATED IN THE ISLAMORADA 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... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed April 24, 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 February 23, 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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    From
    $250
    / Night
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    2 Bedrooms, 2 Bathrooms, Sleeps 4
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Balcony
    • Patio
    • Terrace
    • Satellite TV
    • Linens Provided
    • Refrigerator
    • Stove
    • Towels Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • 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
    From
    $279
    / Night
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    2 Bedrooms, 3 Bathrooms, Sleeps 6
    other traveler has booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    • There Are Tennis...
    • Waterfront
    • Watersports Nearby
    • Air Conditioning
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Islamorada, Florida Keys 33036
    From
    $428
    / Night
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    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Water Views
    • Private Fishing...
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Satellite TV
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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
    From
    $1,350
    / Week
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Ocean Views
    • Waterfront
    • Air Conditioning
    • Shared Tennis Court
    • Private Fishing...
    • Hot Tub
    • Game Room
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to your island paradise! Each time you open the door of this Islamorada vacation home the view of the ocean’s aquamarine color will take your breath away once again. Set just above the tops of softly swaying palm trees, views overlook the Atlantic Ocean, private boat dock, fish station,... View all property information
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    Islamorada, Florida Keys 33036
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    $300
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    1 / 29
    5 of 5 stars (22) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5
    Overview Reviews (22) Make Inquiry
    Overview Reviews (22)
    Amenities & Details
    • DVD Player
    • Stereo System
    • Internet Access
    • Satellite TV
    • Watersports Nearby
    • Waterfront
    • Water Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed August 20, 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 June 30, 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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    $495
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    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 7
    Overview Make Inquiry
    Overview
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    • TV
    • Swingset
    • DVD Player
    • Private Outdoor...
    • Wi-Fi
    • Housekeeping...
    • Watersports Nearby
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay. Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget all the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $165
    / Night
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    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Watersports Nearby
    • Terrace
    • Air Conditioning
    • Linens Provided
    • Grill
    • Wi-Fi
    • Balcony
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Enjoy spectacular water views from the private petite beach, large TIKI hut, boat dock and marina, You'll be just steps away from the ocean, Enjoy spectacular water views and amazing sunsets, just steps away from Founder's park with private beach, private kiddie pool,and play area plus large... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    $2,950
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    1 / 30
    5 of 5 stars (20) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4
    other travelers have booked this property
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Stereo System
    • Sauna
    • Internet Access
    • DVD Player
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen television, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed August 18, 2015
    Our son went to Boy Scout Camp out of Islamorada and my husband and I stayed here several days just the two of us and several days with the three of us (my husband, myself, and...
    5 of 5 stars Reviewed July 19, 2015
    This was our second at Summer Sea and Rosella and I will be back again. We met with Richard to gain entry as before, who took the time to show us all the improvements made to...
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    From
    $750
    / Week
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    1 Bedroom, 1 Bathroom, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Children's Pool
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Game Room
    • Sauna
    • Ocean Views
    • Pool Table
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Relax and Unwind in Your Luxuriously Renovated Condo With Oceanfront Views in the Fishing Capital of the World: Islamorada!! Beautiful Open Water Views in a Well-appointed Building That Provides Everything You Need for a Relaxing and Memorable Vacation. the Cozy Patio Invites You to Enjoy Your... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    From
    $258
    / Night
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    1 / 21
    5 of 5 stars (3) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6
    other travelers have booked this property
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    Amenities & Details
    • Internet Access
    • Waterfront
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Private Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed February 7, 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 September 2, 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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    $2,800
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    1 / 41
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Shared Tennis Court
    • Wi-Fi
    • Satellite TV
    • Private Fishing...
    • Air Conditioning
    • Waterfront
    • Watersports Nearby
    • Water Park Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    5 of 5 stars Reviewed July 28, 2015
    The condo was very beautifully furnished. The kitchen had everything we needed. The pool at the complex was really nice. The beach was small but the snorkeling there was great...
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    $2,490
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    3 Bedrooms, 2 Bathrooms, Sleeps 10
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    • Washer
    • Internet Access
    • Dryer
    • Stereo System
    • Air Conditioning
    • DVD Player
    • Deck
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms, 1 bath with a new leather couch that pulls out to a queen size bed. Downstairs an... View all property information
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    Islamorada, Florida Keys 33036
    From
    $250
    / Night
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    2 Bedrooms, 3 Bathrooms, Sleeps 6
    other traveler has booked this property
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Islamorada, Florida Keys 33040
    From
    $3,000
    / Week
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    4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Terrace
    • Balcony
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Private Outdoor...
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Tarpon House at Bonefish Bay is one of 12 homes located in Islamorada's premier gated community. Each home features a private pool and hot tub, and guests are welcome to enjoy the common amenities such as beach, tennis court and playground. The house comes with kayak, paddleboard, and bicycles.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $4,500
    / Month
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    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Satellite TV
    • Waterfront
    • Private Fishing...
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Children's Pool
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    AVAILABLE: Present through November 26, 2015. April 2016 and beyond. KINDLY NOTE: MONTHLY RENTAL. To maintain the beauty of Beacon Reef, rental contracts must be for no less than a month. This helps keep the property exclusive, serene and beautifully respected--something you will truly enjoy... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $4,000
    / Week
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    5 Bedrooms, 5 Bathrooms, Sleeps 10
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    • Air Conditioning
    • TV
    • Private Outdoor...
    • Waterfront
    • Water Views
    • Hot Tub
    • Ocean Views
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Islamorada Venetian Shores luxury waterfront 5BD/5BA with 100' dock and boat lift, custom pool with spa and waterfall, elevator & private master suite on the 3rd floor. Instant big boat access to both the ocean and bay from 100' wide, deep canal. Spacious home offers over 5,000 sf including porches... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,290
    / Month
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    2 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Waterfront
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Watersports Nearby
    • Wi-Fi
    • Swingset
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Canal-front house, quiet and in the nicest of neighborhoods (Plantation Key Colony). Situated on the bayside on Mile Marker 90. All remodeled,white tiled floor, furnished in wicker/rattan and decorated with the ocean & beach ambiance in mind. Boat dockage in the back and easy access to few boat... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    From
    $1,596
    / Week
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Air Conditioning
    • Water Park Nearby
    • Ocean Views
    • Private Fishing...
    • Water Views
    • TV
    • Wi-Fi
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
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    Islamorada, Florida Keys 33036
    From
    $2,350
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    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 5
    Overview Make Inquiry
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    • Shared Outdoor Pool...
    • Hot Tub
    • Gym
    • Balcony
    • Internet Access
    • Patio
    • Satellite TV
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY: 29 DAYS Exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen with Corian counters,... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $120
    / Night
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    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Amenities & Details
    • Shared Tennis Court
    • Satellite TV
    • Private Tennis Court
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Internet Access
    • Private Fishing...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Islamorada, Florida Keys 33036
    From
    $5,000
    / Month
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    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Amenities & Details
    • Refrigerator
    • Washer
    • Air Conditioning
    • Internet Access
    • Patio
    • Dryer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Spacious 3/3 canal front home in Lower Matecumbe. 75 Ft of dock with 45 FT cut-in for extra boat protection. Walk down the street to world famous Robbies for dinner/drinks and boat, kayak and jet-ski rentals. Located on MM 77, this place is close to many restaurant and tourist sites. Just a few... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $1,600
    / Month
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    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Dryer
    • Washer
    • DVD Player
    • Patio
    • Air Conditioning
    • Water Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Park Model mobile home located oceanside on beautiful Windley Key in Islamorada, Florida Keys, the 'sport fishing capital of the world.' This is a great spot for relaxing, fishing and/or exploring the Keys, situated 75 miles from Miami and 85 miles from Key West. 1 BR plus upstairs sleeping or... View all property information
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    Islamorada, Florida Keys 33036
    From
    $170
    / Night
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    1 / 26
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Overview Reviews (1)
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Water Views
    • Dryer
    • Grill
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Sol Y Mar SOL Y MAR is 2,500Sq.Ft. of Living Space,Three (3) Bedrooms, Two (2) Bathrooms on Three (3) Levels. Property is located in Tavernier, in Islamorada, Florida (MM90). The Center of the Keys, 1.5 Hours to Miami, 1.5 Hours to Key West; Shopping, Restaurants, Theaters, Sunset... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed April 25, 2015
    Our family of 5 adults spent a week at Sol Y Mar in Tavernier Florida. We were fortunate to have Nestor Loredo as our agent. The house was all as promised. Nestor met us the and...
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    From
    $179
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    1 Bedroom, 1 Bathroom, Sleeps 3
    other traveler has booked this property
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    • Air Conditioning
    • Shared Outdoor Pool...
    • Watersports Nearby
    • Housekeeping...
    • DVD Player
    • Stereo System
    • Wi-Fi
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    From
    $18,000
    / Month
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    1 / 11
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Overview Reviews (1)
    Amenities & Details
    • Air Conditioning
    • Private Outdoor...
    • Waterfront
    • Water Views
    • Internet Access
    • Satellite TV
    • Boat Available
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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 June 16, 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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    $3,255
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    1 / 49
    5 of 5 stars (6) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Watersports Nearby
    • Air Conditioning
    • Private Outdoor...
    • Water Views
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    FOR ADDITIONAL REVIEWS GO TO 'HOMEAWAY.COM' LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS IF YOU GET A RESPONSE FROM BESTHOLIDAYRENTALS.COM **** IGNORE IT **** SCAM MINIMUM STAY 7 NIGHTS, MAXIMUM OCCUPANCY 6 PPL, RENTAL PATTERN... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed May 13, 2014
    We had such a wonderful time at Paradise Point!! The views were beautiful!!! The kids loved the pool and all the sealife we saw. Many fish and stingrays, just to name a few...
    5 of 5 stars Reviewed February 13, 2014
    My week started when my wife and I along with our two friends met Juan Sanchez at this home he calls Paradise (which it really is). The man from my first e mail to him to locking...
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    $800
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    1 / 45
    5 of 5 stars (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Watersports Nearby
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    * 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)... View all property information
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    Islamorada, Florida Keys 33036
    From
    $1,500
    / Night
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    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • TV
    • Stereo System
    • DVD Player
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    About this property
    The Royal Palm, South - Ocean Front Home ( recent fraud. NEVER wire us money. Payment for reservations can only be done via the phone, not online or via wire) Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil with nothing compromised this luxurious Caribbean home... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed April 24, 2015
    Rolled out of bed early every day this week with my boys and family friends for my favorite commute: 50 yard walk to a private boat slip at the resort. We rented a boat...
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    From
    $139
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    1 Bedroom, 1 Bathroom, Sleeps 2
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    • Grill
    • Shared Outdoor Pool...
    • Stereo System
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • TV
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • 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 YET... View all property information
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    Location Information
    Islamorada, Florida Keys 33136
    From
    $5,000
    / Month
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    1 / 28
    5 of 5 stars (27) Excellent
    Studio, 1 Bathroom, Sleeps 2
    Overview Reviews (27) Make Inquiry
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Water Views
    • Air Conditioning
    • Private Fishing...
    • Watersports Nearby
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    PLEASE DO NOT TRY TO BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you a significant amount in FlipKey booking fees. We do not use the optional calendar feature on this listing. This is a very popular rental, so book your preferred dates well in... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed August 28, 2015
    We always try to find a small nice property instead of big international chains in every trip we do and after staying in many hotels of this kind we are 100% sure that Islamorada...
    5 of 5 stars Reviewed April 16, 2015
    Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips...
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    From
    $8,300
    / Week
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    1 / 25
    5 of 5 stars (7) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16
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    Amenities & Details
    • Washer
    • Satellite TV
    • Dryer
    • Grill
    • Water Views
    • Stereo System
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat lift, Tiki hut on private beach, Heated pool and Wireless remote Internet. Southern Diversion has just been completely renovated. Brand new... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed August 18, 2015
    Our family of 13 people enjoyed a full week at this property. The house was amazing along with outstanding views. The property was well clean that includes the yard, pool and...
    5 of 5 stars Reviewed March 28, 2015
    I did not stay here but our friends did and we attended a wedding there and it was amazing. Beautiful place and very clean. I hope my kids get married there!
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    $500
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    1 / 38
    5 of 5 stars (23) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Amenities & Details
    • Private Outdoor...
    • DVD Player
    • Internet Access
    • Waterfront
    • Satellite TV
    • Stereo System
    • Water Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed March 24, 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 May 19, 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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    $12,000
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    1 / 12
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Boat Available
    • Internet Access
    • Deck
    • Water Views
    • Waterfront
    • Satellite TV
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    ****This house cannot rent for less than 28 days, per County Ordinance**** Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Oasis. Oasis is located at Mile Marker 75.6, in beautiful Islamorada. This Beautiful three bedroom, three bath home will sleep 8 people very Comfortably. Besides the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,500
    / Week
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    1 / 19
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Refrigerator
    • Water Views
    • Grill
    • Ceiling Fans
    • Satellite TV
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed May 28, 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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