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Islamorada Vacation Rentals

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    Travelers to Islamorada are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 22
    4.5 of 5 bubbles (13) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 19
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 24
    4 of 5 bubbles (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 25
    5 of 5 bubbles (10) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Wi-Fi
    • Patio
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed September 17, 2015
    We attended with my wife and adult daughters and this apartment had everything we could wish for.The facilities were ideal for our needs and the booking process was simple. Due...
    4 of 5 bubbles Reviewed September 13, 2015
    The condo is very nice and spacious for 5 persons. The place is clean and supplies are adequate. Location is good. Swimming pool is big and nice. Able to do a little fishing...
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    1 / 25
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
    • Parking
    • Wi-Fi
    • Satellite TV
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    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed November 28, 2016
    Fantastic townhouse!! Came here to stay with a couple of friends and went fishing. It is right in the heart of Islamorada. You'll never run out of things to do, or places to eat...
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    1 / 25
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
    • Washer
    • Patio
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed November 10, 2016
    Loved the home. Everything that was advertised was available and easy to use and find. Nice pool, access to the beach, and close to tons of activities. We were here for a family...
    5 of 5 bubbles Reviewed April 20, 2016
    I highly recommend this vacation rental! Very clean the pictures online are exactly what you see when you enter this beautiful home. It’s safe, convenient, well decorated...
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    1 / 18
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed June 14, 2016
    This was our first trip to Florida, it was agreed that we would leave Orlando and the parks for a few years as our children are still quite young (4 and 1). We did extensive...
    5 of 5 bubbles Reviewed January 18, 2016
    We had very nice time staying in Ana's townhouse in Islamorada. It is nicely decorated, well equipped, comfortable and spotlessly clean. There is more than enough room for a...
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    1 / 25
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Terrace
    • Wi-Fi
    • Grill
    • Patio
    • Shared Outdoor Pool...
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 bubbles Reviewed May 1, 2015
    Our townhouse was clean, spacious, & quiet. Lovely updated kitchen and laundry. The pool was delightful, and the beach & dock were very enjoyable as well. Very peaceful...
    5 of 5 bubbles Reviewed March 28, 2015
    I really enjoyed my stay! The place was great. I loved the layout. Very roomy. Enough space for everyone. The pool was great and even played a little tennis.
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    1 / 12
    5 of 5 bubbles (1) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • DVD Player
    • Secure Parking
    • Wi-Fi
    • Housekeeping...
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • 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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed April 12, 2017
    A beautiful place in a quiet neighborhood. Thorn is a wonderful host and the breakfast was delicious!
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    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • DVD Player
    • Grill
    • Patio
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2... View all property information
    Location Information
    Islamorada, Florida Keys 33036
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    1 / 20
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 4-6 people. Enjoy the tennis courts, large pool on the ocean, beach-side BBQ grills. Relax, dine and drink under one of the tiki huts or visit one of the many water-front restaurants and bars nearby.... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 bubbles Reviewed 2 weeks ago
    This condo was perfect for our annual family vacation. The condo was very clean, well-equipped, and the online description was accurate. The owners were excellent to deal with...
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    1 / 19
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Ocean Views
    • DVD Player
    • Terrace
    • Grill
    • Washer
    • Balcony
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Mina Bay - vacation rental with "the million dollar view"! Truly OCEANFRONT on the sandy beach and feet from the pier and dock. Sparkling water's and brilliant sunsets complete this 2 Bd 1.5 Ba plus loft Unit I-1 townhouse. 28 DAY MIMIMUM RENTAL for all guests.  Accommodates a family of 8 perfectly... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed March 12, 2017
    We spent part of the holidays at Mina Bay! The views are stunning! Not to mention you can hear the sound of the waves from the second bedroom - very relaxing! The unit is located...
    5 of 5 bubbles Reviewed January 24, 2017
    Beautiful spacious oceanfront condo fully detailed and furnished in a gated community in Islamorada. The location is perfect and the beach is on the doorstep. Perfect for two or...
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    1 / 21
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Children's Pool
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Sauna
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 bubbles Reviewed October 27, 2016
    This vacation was the perfect relaxing trip we have had in a long time. It is less than 2 hours from Miami airport, which is a beautiful drive. The condo was perfect. If I...
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    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to your beach-front oasis on the bay side at mile marker 74 in Islamorada, the Sport Fishing Capital of the World. Dig your toes in the sand, bask in the warm, clean waters and soak up the sun at this beautiful retreat. For the fishermen and divers there is a shared dock and boat ramp on... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 29
    5 of 5 bubbles (24) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Patio
    • Grill
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 4 weeks ago
    Great place to setup home base in the Keys. The home had everything we needed, including a fully stocked kitchen for cooking our fresh catch. Nice, quiet community with many...
    5 of 5 bubbles Reviewed September 13, 2016
    I highly recommend Islamorada and this was a great place to stay. The house was very clean and everything is right there so you can relax and enjoy your vacation. The...
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    1 / 24
    4 of 5 bubbles (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Grill
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Washer
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** This water front home is located oceanside in the tropical Lower Matecumbe key, Islamorada, mile marker 73 (The Sport Fishing Capital of the World). It features a 15' wood dock and 12’ wide ramp, so you can bring your own boat and... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed October 27, 2015
    This house was absolutely great! I loved that it had a dock and I was able to bring my boat with me instead of having to leave it at a marina. I stayed here for a week with a...
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    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 11
    4.5 of 5 bubbles (4) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Secure Parking
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    3 of 5 bubbles Reviewed December 18, 2016
    Appealing features: Convenient location. The grounds were beautiful, with a little waterfall, trees, plants and interesting art around little sitting areas in the courtyard...
    5 of 5 bubbles Reviewed May 26, 2016
    I recommend this B&B to anyone who just wants a beautiful property to relax and enjoy the company of your significant other. The staff is very attentive and accommodating and the...
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    1 / 25
    4.5 of 5 bubbles (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. Near the house is the small Anne's Beach. There are nature trails, board walks to... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed April 1, 2016
    Three of us stayed for a week in March 2016. Unfortunately two more friends had to pull out due to illness, so we had a surplus of rooms. The house is not the most modern of...
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    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfect catch and enjoy a sunset... View all property information
    Location Information
    Islamorada, Florida Keys 33036
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    1 / 41
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium... View all property information
    Location Information
    Islamorada, Florida Keys FL 33036
    5 of 5 bubbles Reviewed February 2, 2016
    We loved our stay at Ocean Harbour Apartments. After viewing photos on your website, we chose this based on the beautiful grounds and lovely accomodations. We could not have...
    5 of 5 bubbles Reviewed January 5, 2015
    This spacious condo is beautifully furnished and equipped. The gated community is very quiet and has a heated salt water pool. There is a nice spot to see the moon and sunrise...
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    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium complex with heated out door pool, gym, plenty of parking, secured entrances, elevator, and quiet. My condo is kept meticulously with attention to detail. Linens, towels and pool towels are included in the... View all property information
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    Islamorada, Florida Keys 33070
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
    • Hot Tub
    • Shared Outdoor Pool...
    • Grill
    • Balcony
    • Satellite TV
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    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Infinite ocean views from the large balcony at this modern and luxurious oceanfront condo at mile marker 87. BOAT SLIP INCLUDED which can accommodate up to a 30' boat. SLEEPING ARRANGEMENTS (Sleeps 4) Master Bedroom: - King Size... View all property information
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    Islamorada, Florida Keys 33036
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 37
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
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    • ?
    About this property
    Beautiful 2 bedroom 2 bath, condo with everything that you need for a perfect relaxing vacation. Balcony access off your living room and master bedroom that overlooks the newly remodeled pool and jacuzzi as well as the beach and ocean. The complex is oceanfront and this unit has ocean views. Some... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor...
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    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. Offering Modern Granite Counter Tops and Stainless Steel Appliances. Plush... View all property information
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    Islamorada, Florida Keys 33070
    1 / 21
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Sauna
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. For two couples or a family with 2 kids. The two new extra long twin beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new king bed, ocean view and private bath. 2nd bathroom in hallway. This... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 bubbles Reviewed July 10, 2016
    Beautiful ocean views! Nicely decorated and well-cared for condo. We hope to return next year. We had everything we needed and felt like we were at home, a lovely relaxing home.
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    1 / 13
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Waterfront
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our cottage is located in a quaint and quiet neighborhood on a deep water canal, Bayside at Mile Marker 89. A concrete boat dock is available for a 30 foot boat and a fish cleaning station. There is easy ocean access through Snake Creek or Tavernier Creek. The fenced private back garden has a... View all property information
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    Islamorada, Florida Keys 33070
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 19
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed November 24, 2016
    very neat and clean. Great location and views. Easy access to all of the Keys. Spacious nice size kitchen for cooking a meal if you feel like it. Nice location, because it's far...
    5 of 5 bubbles Reviewed July 22, 2016
    This place was in a great location, beautiful view, nicely furnished, perfect in every way. Would definitely stay next time I'm in the area!
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    1 / 35
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    This townhome at Executive Bay will sure make your home away from home!  This unit has been completely renovated and decorated beautifully.  This 2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a... View all property information
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    Islamorada, Florida Keys 33036
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Rental amount includes all fees boat dock fee.. This newly renovated modern 4th floor condo in a private gated community has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened in Lanai, 2 lighted tennis courts, and... View all property information
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    Islamorada, Florida Keys 33036
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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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    Islamorada, Florida Keys 33070
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    Spacious and impeccably remodeled luxury two-bedroom condo. Elegantly furnished by renowned designer. Italian ceramic flooring throughout, new gourmet kitchen with top of the line stainless steel appliances, designer bathrooms and walk-in closets. The Grand is a waterfront luxury full service... View all property information
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    Islamorada, Florida Keys 33132
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,800 per... View all property information
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    Islamorada, Florida Keys 33036
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    "The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the... View all property information
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    Islamorada, Florida Keys 33036
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    2 of 5 bubbles (2) Poor
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    This unit's kitchen, bathrooms, windows, and doors received a facelift in January 2014! Enjoy the spectacular view of the Florida Bay from either one of the TWO balconies in this 2 story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, flat panel TV's in the... View all property information
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    Islamorada, Florida Keys 33036
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    Beautiful 4 bedroom 4.5 bath home located in Venetian Shores.  The home has a great kitchen that opens up to the living room.  You can even play a game of pool in the room off the living room.  Upstairs there is a master suite that has a great porch that you can sit and enjoy your morning coffee... View all property information
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    Islamorada, Florida Keys 33036
    1 / 15
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This lovely property is part of a gated,... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed March 25, 2015
    Great property! Very beautifully decorated. I loved the view, really enjoyed my stay! I look forward to staying there again soon!
    5 of 5 bubbles Reviewed January 19, 2015
    This condo is beautifully decorated and chock full of everything you need to make your stay just perfect. The condo and the complex are extremely well maintained and have the...
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    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    This premier luxury home is situated in a very quiet and peaceful gated community. All the rooms are very spacious with quality furnishings. A large double wide lanai with breathtaking views will make your getaway in the Keys. For your enjoyment it comes with private boat dockage, covered parking,... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed January 2, 2017
    This condo is beautiful, clean and has great amenities (swimming pool, hot tub, tennis court and gym). Everything in the condo is first class with excellent quality of furniture...
    5 of 5 bubbles Reviewed January 2, 2017
    This condo was gorgeous and well stocked. They kept a collection of brochures for all the activities around the area in the condo. We loved swimming in the pool and fishing in...
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    • Patio
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    Keys home in Anglers Reef with ocean view, dock, community pool & private beach This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef... View all property information
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    Islamorada, Florida Keys 33036
    1 / 31
    4.5 of 5 bubbles (7) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed March 25, 2015
    We had a terrific time at 137 Lessara this February. The wildlife (birds, fish, manatee) viewing was incredible, the weather great, and the house was fantastic- especially the new...
    4 of 5 bubbles Reviewed June 5, 2014
    This house had more than enough of everything needed away from home.The decks on both floors were great for relaxing,visiting, grilling and tanning.Plenty of space our three...
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    MINIMUM STAY: 29 DAYS - Available this winter! Very comfortable 50ft dock, wide canal, home located close to Tavernier Creek Channel with easy access to the Gulf and Atlantic. Great fishing, kayaking and diving. Concrete dock, fish cleaning station . 1.5 mile north of the world famous Holiday... View all property information
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    Islamorada, Florida Keys 33070
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage.... View all property information
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    Islamorada, Florida Keys 33036
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Yard
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    Beautiful 1 BDRM apartment located in Islamorada. Full kitchen and 1 full bath. Home is located on canal within 100 yards of the ocean. You will enjoy access to fully screened and heated pool. WiFi and cable TV included. Close proximity to shopping, restaurants and all the best the Keys have to... View all property information
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    Islamorada, Florida Keys 33070
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to Modern Keys Living with Bay Views! New from top to bottom!!! Newly remodeled and beautifully decorated 1st floor corner unit with a private entrance. Enjoy the mix of vintage and new furniture and the most comfortable sofas, beds, linens and more! This home is equipped with everything... View all property information
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    Islamorada, Florida Keys 33070
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Property description Framed by mangroves and the Atlantic Ocean this exquisite Key West style 2 bedroom, 2.5 bathroom home, is located in the quiet oceanfront private community of Anglers Reef -one of the best kept secrets in the Keys. Florida State Licensed Single Family Vacation Rental Dwelling... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    5 of 5 bubbles (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees.  This home sits directly on the bay and has 2 bedroom 2 bath upstairs and has a 2 bedroom 1 bathroom apartment.  The home is located at mile marker 76. Near the... View all property information
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    Islamorada, Florida Keys 33036
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a 2 bedroom and 2-1/2 bath unit.  There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the... View all property information
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    Islamorada, Florida Keys 33070
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    About this property
    Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex consisting of 70 units. Enjoy wonderful Bay views and sunsets from our two bedroom / two bath condominium unit that sleeps up to 6 people. Stay in... View all property information
    Location Information
    Islamorada, Florida Keys 33070
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    • Local time: 06:46 AM (EDT)
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