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Rentals with Pools in Islamorada, FL

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    1 / 19
    5 of 5 stars (3) Excellent
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 41
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 stars (3) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars 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...
    5 of 5 stars Reviewed September 9, 2015
    Enjoyed my 2 night stay. Bombay room was quiet, uniquely furnished, clean, and well-air conditioned. Refreshing pool and nice seating areas with plantings, water features, and...
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    1 / 18
    5 of 5 stars (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our unit is a short walk to the beach and dock... 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 fishing/dock. The townhouse has 2... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars 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 stars 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 / 23
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • 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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    Islamorada, Florida Keys 33070
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Balcony
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    • ?
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    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 4-6 people. Enjoy the tennis courts, large pool on the ocean, beach-side BBQ grills. Relax, dine and drink under one of the tiki huts or visit one of the many water-front restaurants and bars nearby.... View all property information
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    Islamorada, Florida Keys 33070
    1 / 14
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • 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
    1 / 4
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    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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    Islamorada, Florida Keys 33036
    1 / 5
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    Malaysian room is poolside in a tropical atmosphere facing a beautiful waterfall. Features a mini kitchen with blender, coffee maker, microwave, refrigerator and toaster oven. A/C, heat, TV and WiFi. Includes a full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO... View all property information
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    Islamorada, Florida Keys 33036
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    1 / 61
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • x
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    key Lime Villa 3 Bring your friends and family to the Florida Keys and stay in this beautiful 3 bedroom villa rental with community pool, boat dock and plenty to do! This brand new 3 bedroom Islamorada vacation villa is in the Art District and you'll enjoy the marinas, fine dining, entertainment... View all property information
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    Islamorada, Florida Keys 33036
    1 / 62
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
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    Key Lime Villa 1 - Family and friends will love this brand new 3 bedroom Islamorada vacation villa in the Art District, close to fine dining, marinas and entertainment while enjoying breathtaking sunset views. Amenities. 3 bedrooms, 3.5 baths, a gourmet kitchen and world class amenities including,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 54
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • x
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    Key Lime Villa 2 You won't want to leave this brand new 3 bedroom Islamorada vacation villa in the Art District. Everyone will enjoy the renowned restaurants, fine dining, sunset celebrations, entertainment, marinas and breathtaking sunsets. Amenities. 3 bedrooms, 3.5 baths, a gourmet kitchen and... View all property information
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    Islamorada, Florida Keys 33036
    1 / 63
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
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    Conch Villa 4 From this beautiful brand new 3 bedroom Islamorada vacation villa in the Art District, you'll enjoy the marinas, fine dining and entertainment while enjoying breathtaking sunset views. Amenities. 3 bedrooms, 3.5 baths, a gourmet kitchen and world class amenities including, Free Wi-Fi,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 62
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    Bay Villa 7, From the vantage of this brand new 3 bedroom Islamorada vacation villa in the Art District, you'll enjoy the marinas, fine dining and entertainment while enjoying breathtaking sunset views. Amenities. 3 bedrooms, 3.5 baths, a gourmet kitchen and world class amenities including, Free... View all property information
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    Islamorada, Florida Keys 33036
    1 / 61
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
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    Bay Villa 9 From the vantage of this brand new 3 bedroom Islamorada vacation villa in the Art District, you'll enjoy the marinas, fine dining and entertainment while enjoying breathtaking sunset views. Amenities. 3 bedrooms, 3.5 baths, a gourmet kitchen and world class amenities including, Free... View all property information
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    Islamorada, Florida Keys 33036
    1 / 63
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
    • ?
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    • ?
    About this property
    Bay Villa 8 From the vantage of this brand new 3 bedroom Islamorada vacation villa in the Art District, you'll enjoy the marinas, fine dining and entertainment while enjoying breathtaking sunset views. Amenities. 3 bedrooms, 3.5 baths, a gourmet kitchen and world class amenities including, Free... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 36
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Conch Villa 5 Brand new, 3 bedroom Islamorada vacation villa in the Art District, you'll enjoy the marinas, fine dining, entertainment and breathtaking sunset views. Amenities. 3 bedrooms, 3.5 baths, a gourmet kitchen and world class amenities including, Free Wi-Fi, Community Swimming Pool, Tiki... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Sauna
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. For a couple with 2 kids or two couples. The two new extra long twin beds in 2nd bedroom convert to a comfy King Bed! This direct oceanfront, well-cared for 5th floor corner unit is right on the ocean in Islamorada at... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars 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 / 4
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    • ?
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    • ?
    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
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    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Wonderful two story townhome in a private, gated community with all amenities you'd expect while on vacation. Inside: Newly renovated and remodeled unit. Fully equipped kitchen and stainless appliances, large storage cabinets with pull outs. Granite counters etc. Living room area with 60 inch... View all property information
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    Islamorada, Florida Keys 33036
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Premier condo in Islamorada in Upper Florida Keys. Located on 12-acre property with 1,100 feet of oceanfront. Gated complex, large swimming pool, sand beach, and two tennis courts as well as boat ramp and dedicated slip. Spectacular Atlantic Ocean views. This top-floor, freshly-remodeled 2 bed 2... View all property information
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    Islamorada, Florida Keys 33036
    1 / 7
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    A small stand alone room in the corner of the garden. Features a/c, coffee maker, free WiFi, grill on premises, heat, microwave, refrigerator, shared bathroom with one other couple, TV and includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO FISHING, DIVING,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Children's Pool
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    • ?
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    • x
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on... View all property information
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    Islamorada, Florida Keys 33023
    1 / 25
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    <b> Minimum Rental: 7 Nights (Saturday to Saturday)</b> BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open... View all property information
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    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed March 22, 2016
    Brockhaus was exceptional! Everything we could have needed was provided and the property is fabulously maintained! It was exactly as pictured and immaculate. I was a little...
    5 of 5 stars Reviewed October 5, 2015
    We came for 10 days to celebrate my husband's 70th birthday. Wow! The views from the balcony and in three directions - all onto the water - were amazing. Gorgeous...
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    1 / 9
    5 of 5 stars (1) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 50 | Quick View
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    • x
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    About this property
    jaouoroqoaueo9quoruroqwu9euour99n9n9r9wur9ue9adouafiuaeoufasljfaof0askr;oasd-fsd4fas8/da5se/xgv5asqe-0taa8asdg=as9ufaoefauoatwouoasujfgaseuroue9rtasofuoasuaweroasufoauf0aasf5asf6asf6as6f6aseoufawi9rayweriyawiywririyseiyaweiryqwiryiweykcasdyvkshvckcaicaeiycaiyaisyaivyiseyvaifyksdhfikzhfisadkasrhisdhf... View all property information
    Location Information
    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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    1 / 31
    5 of 5 stars (23) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    • x
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    • 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
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed May 1, 2016
    Absolutely fantastic facilities in a wonderful setting. From the time we booked this place until the time we left we had an amazing experience. The flat is really well...
    5 of 5 stars Reviewed April 29, 2016
    Absolutely loved staying here. We enjoyed the home away from home feel, and also a beautiful view of the ocean from the balcony. Very comfortable, and quiet. The owner was so...
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    1 / 33
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    WE DO NOT ACCEPT WIRE TRANSFERS AS PAYMENT...ALL PAYMENT IS THROUGH FLIPKEY 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,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
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    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.<BR><BR>Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    <b> Minimum Rental: 1 Month </b> Charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. You will enjoy your... View all property information
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    Islamorada, Florida Keys
    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set... View all property information
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    Islamorada, Florida Keys 33036
    1 / 45
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    * 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
    1 / 13
    4.5 of 5 stars (16) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please send us an inquiry or call us for availability. We have a couple of units. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool, sandy beachy area, and fishing pier with flats boat dockage (drawing 24" or less) located directly on the ocean.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    3 of 5 stars Reviewed April 10, 2015
    Overall this was a good choice for our 2 week stay. We were within reasonable distance from both Key Largo and Marathon, and there were numerous attractions and activities close...
    4 of 5 stars Reviewed August 3, 2014
    Nice townhome with water view, easy drive to activities in Islamorada, Tavernier, and Key Largo. Townhome is 3 levels, lots of stairs, narrow staircases. Clean, updated, kitchen...
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    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 stars (6) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 3 weeks ago
    Each year we travel to the Keys for lobster season. This year we were very happy with our choice of accomodations. The condo is in a great location with easy access by boat to the...
    5 of 5 stars Reviewed January 5, 2016
    The Lobinskys, the owners, were responsive, informative, and extremely helpful. We traveled as a family with our two teenagers and our boat. Chris and Deanna provided options...
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    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two... View all property information
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    Islamorada, Florida Keys 33036
    1 / 29
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    <b>Casa Dorado</b> is an exceptional privately owned single family home located directly on Florida Bay on Lower Matecumbe Key in Islamorada. The house is named after the owners' favorite species of fish, the Dolphinfish, also known as Dorado in Spanish speaking coastal areas. With the green roof... View all property information
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    Islamorada, Florida Keys
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    <b> Minimum Rental: 1 Month </b> Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2... View all property information
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    Islamorada, Florida Keys 33036
    1 / 12
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    <b> Minimum Rental: 1 Month </b> Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina. You'll be able to see cruise ships as they pass by Alligator... View all property information
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    Islamorada, Florida Keys 33036
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Oceanfront splendor on the Atlantic ocean. Has a 350' pier that can accomodate most any size boat. Just relax by the pool on those hot days or take a dip in the ocean. The pool is heated for the winter months. The house is extremely private. There is a wooden fence around the house and... View all property information
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    Islamorada, Florida Keys 33070
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Located on the peaceful, northern end of Islamorada, in the quite residential neighborhood of Venetian Shores. Just 75 miles from Miami Airport and 86 miles from Key West. Venetian Tropics boasts large rooms furnished in rattan and decorated with a tropical flair. Coconut palms, hibiscus and other... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    <b>Monthly Rental: </b> This 5th Floor unit is located in one of Islamorada's favorite condo complexes. Newer owners have begun renovations. The entire unit has been freshly painted and the décor is being updated. The master bath has been totally gutted and replaced and is brand new. You'll love... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Two Oceanfront villas on two beautiful acres. It has a total of three bedrooms and two and half baths. Sleeps 8-10 comfortably. One King bed, two queen beds, two twin beds, and two queen size pull out sofas. Both villas have full kitchens, living area, lots of windows with gorgeous Ocean and beach... View all property information
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    Islamorada, Florida Keys 33036
    1 / 39
    5 of 5 stars (27) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed March 28, 2016
    This is my fourth year at the property and it has only gotten better. There were some criticism of the deck conditions and lack of refrigerator at the outside Tiki hut. Those...
    5 of 5 stars Reviewed January 12, 2016
    Traveled with a family of 6 Christmas Week 2015. The unit is larger and nicer then it appears in the pictures. The Great room that encompasses the Kitchen, dining, and living...
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    1 / 49
    5 of 5 stars (14) Excellent
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
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    Got a large group that wants to "get away from it all"? Or do you need lots of space for a family reunion or wedding? This is the perfect solution! Terrific location, beautiful view, two private pools for you to enjoy... And since it's 4 separate homes, you aren't right on top of each other. Wide... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed April 13, 2016
    Three families (total of 12 people, teenagers to parents in the 50's) occupied one three bedroom and one two bedroom. The homes and furnishings were in decent shape but some...
    5 of 5 stars Reviewed March 7, 2015
    Great location. Very clean and relaxing. If you are looking for a waterfront view, this place does not have it but it is only a very short walk down to the dock to have a...
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    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
    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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    1 / 38
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 5 weeks ago
    After 10 years of going to islamorada this is the best all round rental house for location, boating and quality. We have rented 7 different properties and this has it all
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    1 / 29
    5 of 5 stars (22) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    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 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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    1 / 27
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed March 1, 2016
    The intent of this trip was to relax and do a lot of fishing. Not only was the property clean comfortable and private it provided great fishing off the pier. While my son and I...
    5 of 5 stars Reviewed September 15, 2015
    The pool, the point, the palms...Great fishing with the kids and snorkeling for the big kids! Dozens of Iguanas to provide entertainment, too. We were all blown away with this...
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