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House Rentals in Islamorada, FL

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    Travellers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 22
    4.5 of 5 stars (13) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 9
    5 of 5 stars (3) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 19
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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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
    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This is a tropical vacation home away from home and is located in the heart of The Florida Keys. Perfect for families, couples, or a friends getaway. Our beautiful house has 3 bedrooms & 2 baths, and can sleeps 6 to 8 comfortably. It has a full kitchen with a spacious living room, plenty of... View all property information
    Location Information
    Islamorada, Florida Keys
    5 of 5 stars Reviewed 17 August 2016
    We just returned from a week at this house. We had a great time, it is really well equipped, nice to have lots of beach and bath towels, huge fridge and freezer, and the laundry...
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    1 / 14
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Grill
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    • Pet-friendly
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    • x
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    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
    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
    • DVD Player
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    • Satellite TV
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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 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
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    Islamorada, Florida Keys
    5 of 5 stars Reviewed 10 July 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 / 40
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
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    • 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
    5 of 5 stars 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 stars 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 / 19
    5 of 5 stars (3) 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
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    • 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
    5 of 5 stars 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!
    5 of 5 stars Reviewed 11 February 2016
    Great place. The condo was exactly as described in Tripadvisor. Located halfway between Miami and Keywest it is the perfect place to sight see the keys from.
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    1 / 7
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • DVD Player
    • Secure Parking
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    • Shared Outdoor Pool...
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    • 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
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    Islamorada, Florida Keys
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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
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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
    1 / 29
    4.5 of 5 stars (4) 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
    ***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! **We do not use the optional calendar feature on this listing. ** This is a very popular... View all property information
    Location Information
    Islamorada, Florida Keys
    3 of 5 stars 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 stars 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 / 5
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    • DVD Player
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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
    1 / 21
    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
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    Islamorada, Florida Keys
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Balcony
    • Satellite TV
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    • Terrace
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
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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
    1 / 17
    5 of 5 stars (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
    • Internet Access
    • Parking
    • Washer
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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
    5 of 5 stars Reviewed 6 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...
    5 of 5 stars Reviewed 21 September 2015
    Awesome house. Modern furnishings makes this rental a standout. Being able to keep your boat here is a real plus. Fast access to the reefs for some amazing diving. The local...
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    1 / 18
    5 of 5 stars (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
    5 of 5 stars 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 stars 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 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the "Sport Fishing Capital of the World". Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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    Islamorada, Florida Keys
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Central Heating
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    • Pet-friendly
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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
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    Islamorada, Florida Keys
    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • Waterfront
    • DVD Player
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    • Ocean Views
    • Air Conditioning
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Wake up every morning and walk right out to your private wrap deck and relax with the sound of the ocean right under your feet. We have a beautifully decorated and updated one bedroom trailer. Kick back in a open concept living room and kitchen with all new appliances. and with stunning views.... View all property information
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    Islamorada, Florida Keys
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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
    1 / 23
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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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
    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
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    Islamorada, Florida Keys
    1 / 25
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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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
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    Islamorada, Florida Keys
    1 / 31
    5 of 5 stars (23) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
    • Wi-Fi
    • Children's Pool
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    • Air Conditioning
    • Satellite TV
    • Ocean Views
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    • 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
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    Islamorada, Florida Keys
    5 of 5 stars 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 stars 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 / 29
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • 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
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    Islamorada, Florida Keys
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    • x
    About this property
    Please call or email to inquire about specific dates. We can be accommodating depending on your dates and needs. Come experience the Keys vibe the way locals do it. This cute, cozy and totally remodeled mobile home is located in the heart of the Keys. It is close to everything (shops,... View all property information
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    Islamorada, Florida Keys
    1 / 8
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • x
    About this property
    Located at mile marker 76 overlooking a beautiful canal leading to the Atlantic Ocean. Boat slip available for the adventurous types. Kayaks for those wanting to explore the local mangroves. Borrow a bicycle and peddle your way through the lower matecumbe via bike path. Don't forget to visit... View all property information
    Location Information
    Islamorada, Florida Keys
    5 of 5 stars Reviewed 31 March 2016
    This is our last day of our month long stay in paradise. Our unit has been totally updated, is very clean and we are very sad to leave. Our boat is right outside our door...
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautifully furnished 2 BR 2 BA Condo on second floor.(First is parking only) Spiral Staircase directly down to lushly landscaped grounds. Only this floor has the stairs, others have to go through a lobby with a key. Wander around among our beautiful tropical gardens, bring your drink down to the... View all property information
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    Islamorada, Florida Keys
    1 / 21
    5 of 5 stars (6) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club... View all property information
    Location Information
    Islamorada, Florida Keys
    5 of 5 stars Reviewed 31 July 2016
    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 5 January 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 / 25
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • x
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    • x
    About this property
    <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
    Location Information
    Islamorada, Florida Keys
    5 of 5 stars 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...
    5 of 5 stars Reviewed 5 October 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 / 19
    5 of 5 stars (6) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Satellite TV
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    <b> Minimum Rental: 7 Nights </b> You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who treasure... View all property information
    Location Information
    Islamorada, Florida Keys
    5 of 5 stars 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 stars 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 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    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
    1 / 25
    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
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Waterfront
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    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
    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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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
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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
    1 / 42
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    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
    1 / 6
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    License #: VR-215, DWE5403682 This resort style community is located at mile marker 85 in Islamorada and is situated directly on the Atlantic Ocean with fantastic views. The community is beautifully landscaped and has a large community pool (heated year-round) that overlooks the ocean! The... View all property information
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    Islamorada, Florida Keys
    1 / 6
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    <b> Minimum Rental: 1 Month </b> Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of the Atlantic... View all property information
    Location Information
    Islamorada, Florida Keys
    5 of 5 stars Reviewed 14 September 2015
    We have always enjoyed the keys and love staying at the Palms of Islamorada. The units are big enough and the amenities are nice. Unit 214 was nice and clean. A big TV for me. The...
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    1 / 27
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    <b> Minimum Rental: 7 Nights </b> Lower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit... View all property information
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    Islamorada, Florida Keys
    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity to... View all property information
    Location Information
    Islamorada, Florida Keys
    5 of 5 stars Reviewed 13 August 2014
    Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.
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    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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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
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
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    <b> Minimum Rental: 1 Month </b> This exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure to look at the... View all property information
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    Islamorada, Florida Keys
    1 / 30
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
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    <b> Minimum Rental: 7 Nights </b> Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each... View all property information
    Location Information
    Islamorada, Florida Keys
    5 of 5 stars Reviewed 2 July 2013
    We have rented the upper duplex of Little Bay in April for the last few years. it is a beautiful property in a perfect setting. The grounds are kept immaculately and the area by...
    5 of 5 stars Reviewed 5 November 2012
    We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach! The...
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    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
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    Islamorada, Florida Keys
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
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    <b> Minimum Rental: 1 Month </b> Comfortably furnished and ready for you. Conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters, or watch the spectacular sunsets over the... View all property information
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    Islamorada, Florida Keys
    1 / 15
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
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    <b> Minimum Rental: 1 Month </b> 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
    1 / 12
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
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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
    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    ***********************FALL SPECIAL: October thru December Rent $4000/MO ***************************** MINIMUM STAY 29 DAYS. BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This home was completely remodeled in 2013. There is 936... View all property information
    Location Information
    Islamorada, Florida Keys