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Villas and Holiday Rentals in Islamorada, FL

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    Travellers to Islamorada are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 9
    4.5 of 5 bubbles (4) Very good
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 16
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 bubbles (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 23
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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 / 14
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Grill
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    • Pet-friendly
    • Child-friendly
    • 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 / 22
    4.5 of 5 bubbles (13) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • ?
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    About this property
    Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes <BR>Wifi, boat dock, trailer parking, and all amenities are included also, <BR><BR>Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee... View all property information
    Location Information
    Islamorada, Florida Keys 33037
    5 of 5 bubbles Reviewed 6 June 2016
    Wonderful vacation nice, relaxing. I would definitely return. Charlie was very informative on where to go to eat. Locals were very nice too.
    4 of 5 bubbles Reviewed 16 October 2015
    What a great little spot! Was quiet and very peaceful. Clean and cozy! Had everything we needed. Will be back to Stay again soon! :)
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    1 / 5
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    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
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
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    About this property
    Rental amount includes all fees boat dock fee.. This newly renovated modern 4th floor condo in a private gated community has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened in Lanai, 2 lighted tennis courts, and... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Patio
    • Waterfront
    • Grill
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Islamorada, Florida Keys 33036
    "."
    5 of 5 bubbles Reviewed 9 November 2016
    Everything we expected and more!! Condo very well maintained. Very adequately supplied with everything you need during your stay. Wonderful!! Thank you Susie and Matt for making...
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    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Children's Pool
    • Washer
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Islamorada, Florida Keys 33023
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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
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    • 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 2 February 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 5 January 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 / 18
    5 of 5 bubbles (1) 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
    1 / 4
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 20
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Balcony
    • Ocean Views
    • Hot Tub
    • Waterfront
    • Washer
    • Grill
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This premier luxury home is situated in a very quiet and peaceful gated community. Spacious rooms and large double wide lanai with breathtaking views add to your getaway in the Keys. For your enjoyment it comes with private boat dockage, covered parking, locked storage with bait freezer, bike... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 3 weeks ago
    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 3 weeks ago
    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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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • x
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    • x
    About this property
    Welcome to Modern Keys Living with Bay Views! New from top to bottom!!! Newly remodeled and beautifully decorated 1st floor corner unit with a private entrance. Enjoy the mix of vintage and new furniture and the most comfortable sofas, beds, linens and more! This home is equipped with everything... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
    • Satellite TV
    • Balcony
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    • Pet-friendly
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    • x
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    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
    Location Information
    Islamorada, Florida Keys 33070
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Property description Framed by mangroves and the Atlantic Ocean this exquisite Key West style 2 bedroom, 2.5 bathroom home, is located in the quiet oceanfront private community of Anglers Reef -one of the best kept secrets in the Keys. Florida State Licensed Single Family Vacation Rental Dwelling... View all property information
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    Islamorada, Florida Keys 33036
    1 / 18
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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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 14 June 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 18 January 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 / 29
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Housekeeping...
    • Grill
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This relaxing private home, known as "Windley Cottage" is located in Angler's Reef, Islamorada's premier gated oceanfront community with private beaches, boat docks (available for rent), and a resort-style swimming pool overlooking the boat dock lagoon, beaches, and the Atlantic ocean.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 4
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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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
    Location Information
    Islamorada, Florida Keys 33036
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    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
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    • DVD Player
    • Waterfront
    • Satellite TV
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    • 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 24 November 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 22 July 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 / 29
    4.5 of 5 bubbles (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Patio
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    iF YOUR PLANS CALL FOR LESS THAN A MONTH, PLEASE CONTACT ME. i MAY BE ABLE TO HELP. ***PLEASE INQUIRE ABOUT SPECIAL DISCOUNTED RATES AND SEASONAL AVAILABILITY*** Please contact us for all of our rates! For shorter stays...make sure you have a minimum of 28 days entered in your contact form!... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    3 of 5 bubbles Reviewed 13 August 2016
    House was nice - except we did not feel comfortable - could not feel at ease - felt like we were being watched - paid a lot of money 😕
    5 of 5 bubbles Reviewed 22 April 2015
    My husband and I just returned from Casa Rio. The home was clean and comfortable and quaint. The outdoor area was beautiful, charming and relaxing. We had access to bicycles...
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    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Central Heating
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ****Recently updated paint, furniture and a Beauty Rest Mattress!!**** Looking to escape reality? Look no further! Spacious 1 bedroom/1 bathroom condo located in the newly renovated Summer Seas Condominiums. Sit back and relax at the pool, go swimming at the private beach. Feeling adventurous?... View all property information
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    Islamorada, Florida Keys 33070
    1 / 7
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
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    • ?
    About this property
    A small stand alone room in the corner of the garden. Features a/c, coffee maker, free WiFi, grill on premises, heat, microwave, refrigerator, shared bathroom with one other couple, TV and includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO FISHING, DIVING,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 31
    5 of 5 bubbles (23) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
    • Wi-Fi
    • Children's Pool
    • DVD Player
    • Sauna
    • Air Conditioning
    • Satellite TV
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 televisions, 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 bubbles Reviewed 1 May 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 bubbles Reviewed 29 April 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 / 25
    4.5 of 5 bubbles (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Shared Outdoor Pool...
    • Patio
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Minimum Rental: 7 Nights (Saturday to Saturday) BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open water... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 bubbles Reviewed 3 October 2016
    Everything needed is available to make your holiday memorable. Well appointed accommodations. Location is well away from the highway and very quiet (September is their slow time...
    5 of 5 bubbles Reviewed 22 March 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...
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    1 / 17
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
    • Internet Access
    • Parking
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    • DVD Player
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 bubbles Reviewed 29 November 2016
    Bed Sheets had multiples holes/tears and were scratchy with "Pills" in them. The 2 sofa beds looked fine but were very uncomfortable for sleeping - they sag at the head. The...
    5 of 5 bubbles Reviewed 7 April 2016
    I can't say enough about our most recent vacation rental in the keys. We have been vacationing in Islamorada for years and I can definitely say this is one of the best places we...
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    1 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Waterfront
    • DVD Player
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 19
    5 of 5 bubbles (6) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • ?
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    • x
    About this property
    Minimum Rental: 7 Nights You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who treasure the... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 13 May 2016
    Having been acquainted with the area and having been, physically, all 'round the property, occasionally, but never in it - it was a shocking and wonderful surprise that this...
    5 of 5 bubbles Reviewed 8 February 2016
    A surprisingly tranquil place bearing in mind that it is positioned in its own grounds between two neighbouring resorts. The rental accomodation is the ground floor of a two...
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    1 / 14
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    ***30DAY MIN RENTALThis is a newly remodeled 4 bedroom 2 bath private home on the ocean side (just 3 houses from the open ocean) with ocean views, pool, tiki hut ice machine and all the comforts of home. This home is perfect for family and fishing! Beds: 1 King Bed, 5 Queen Beds View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 29
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Shared Outdoor Pool...
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    • x
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    • Smoking allowed
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    About this property
    Casa Dorado 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 and... View all property information
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    Islamorada, Florida Keys
    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • Pet-friendly
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    About this property
    This home features 4 bedrooms, 2 baths, pool and bar. This home can comfortably accommodate 8-10 people with room to spare. Alluring turquoise ocean and beachfront views. The onsite boat parking provided tremendous privacy and space for you and all of your guest. A private pool and grill that... View all property information
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    Islamorada, Florida Keys 33070
    1 / 21
    5 of 5 bubbles (8) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 1 week ago
    Extremely clean and comfortable condo in a great location. View of sunrise from Master Bed! Beautiful large balcony to enjoy breakfast, drinks. :) Lots of extras- pool, use of...
    5 of 5 bubbles Reviewed 3 November 2016
    This place was absolutely terrific. The amenities exceeded the list and our expectations. We also met some great residents and enjoyed our time thoroughly. Also, Islamorada is...
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    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This beautifully furnished and spacious... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 25 March 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 19 January 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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
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    About this property
    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 / 27
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    About this property
    A Vacation Rental for View Lovers! Best Location in the Complex. Located at MM 90 in Islamorada. Enjoy beautiful panoramic ocean views from your condo 24/7. This condo in this art-deco inspired complex is located in a very peaceful location and not on US 1 so no road noise. Master bedroom... View all property information
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    Islamorada, Florida Keys 33070
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Pet-friendly
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    • x
    About this property
    Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps eight people. Master bedroom has a king bed with access to the balcony. Second bedroom has a queen bed and third one has two twin beds. TVs in every... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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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 / 42
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • x
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    About this property
    Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of Islamorada, Florida. This home features a private beach, 4 bedrooms, 3 ½ baths, family room, living room, game rooms, pool/spa and bar. This home can comfortably accommodate 8-12 people with room to spare.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
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    • ?
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    • x
    About this property
    Experience total seclusion in this ten-unit oceanfront complex called Port of Call, nestled along Millionaire's Row in Plantation Key, Islamorada on the Atlantic Ocean, Mile Marker 88. Outdoor facilities include a heated pool; chickee hut with common area barbecue grills, Volleyball courts on a... View all property information
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    Islamorada, Florida Keys
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    About this property
    MINIMUM STAY: 28 DAYS NEW OPPORTUNITY to LIVE THE LIFE! This 3 Bedrooms and 2 ½ Baths home with POOL, Dock, and all new furnishings make this your opportunity to experience The Florida Keys at its best. Conveniently located on a deep and wide canal with easy access to the Bay or a short ride... View all property information
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    Islamorada, Florida Keys
    1 / 21
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Children's Pool
    • Ocean Views
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    • Pet-friendly
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    • x
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    • 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 27 October 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 / 29
    5 of 5 bubbles (2) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    This custom built 5 bedroom house has been immaculately taken care of and has a proper size elevator and is fully wheel chair accessible. Enjoy your stay in Sereni-key looking out to an endless oasis over a full size, heated lap pool. Lay down in the shade on the soft grass bordering the pool and... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 15 August 2016
    This house was a beautiful place to stay with large common areas for gathering our big group, but with private bedrooms and bathrooms. All the ocean toys we needed. We had a...
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    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This magnificent home with direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Lie in bed and view the Ocean! Home also overlooks the community pool. Anglers Reef is a quiet oceanfront... View all property information
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    Islamorada, Florida Keys 33036
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This unit is a duplex with 2 full Bedrooms and 2 full Baths - plus a loft in the master bedroom that sleeps an additional 2. There is also an electric EZ Bed for larger groups. Also included is a gas BBQ Grill in the back porch and use of any of the recreational items at the unit. Located in the... View all property information
    Location Information
    Islamorada, Florida Keys 34950
    1 / 4
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Located at SuCasa next to Robbie’s Marina where you can hand feed the Tarpon on Lower Matacumbe. This 2-bedroom apartment sleeps four comfortably in two bedrooms each with a queen-sized. It has a fully equipped kitchen with a stove, dishwasher, microwave, coffee maker, blender and all the... View all property information
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    Islamorada, Florida Keys 33036
    1 / 39
    5 of 5 bubbles (28) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • Waterfront
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    • ?
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    • 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 me for the application. Weekly vacation rental... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed 19 September 2016
    Over the years, we have stayed here 4 times, and each time gets better due to the improvements to the property. The location is perfect and relaxing for folks who like to fish, or...
    5 of 5 bubbles Reviewed 28 March 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...
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    SuCasa is located next to Robbie’s Marina where you can hand feed the Tarpon on Lower Matacumbe. The Main House sleeps eight comfortably in four bedrooms with 3 queen-sized beds and two twin beds and comfortably sleeps 8. It has a fully equipped kitchen with a stove, dishwasher, microwave, coffee... View all property information
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    Islamorada, Florida Keys 33036
    1 / 15
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    • x
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    • x
    About this property
    Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • x
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    • x
    About this property
    Monthly Rental: 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 the... View all property information
    Location Information
    Islamorada, Florida Keys 33036