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Pet Friendly Holiday Rentals in Islamorada, FL

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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 / 41
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    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 33036
    5 of 5 stars Reviewed 1 week ago
    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 / 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
    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    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 33036
    1 / 23
    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 / 19
    5 of 5 stars (6) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    <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
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 14 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 9 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 / 4
    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    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
    1 / 4
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    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
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    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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 square feet of living area on the main level with 2 bedrooms, a full bath and an open living area. On the ground... View all property information
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    Islamorada, Florida Keys 33070
    1 / 30
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 33036
    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 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 14 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 / 27
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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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 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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    <b> Minimum Rental: 1 Month </b> Location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in this home. It is... View all property information
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    Islamorada, Florida Keys 33036
    1 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    <b> Minimum Rental: 1 Month </b> You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. It is located... View all property information
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    Islamorada, Florida Keys 33036
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    <b>MINIMUM STAY: 29 DAYS</b> <b>LYONS LANDING</b> is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home. 3 bedrooms and two baths on the upper level plus a... View all property information
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    Islamorada, Florida Keys
    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
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    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal.... View all property information
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    Islamorada, Florida Keys 33036
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • Private Garden
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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
    Location Information
    Islamorada, Florida Keys 33070
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Porch
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    About this property
    This oceanfront resort is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture built in 2007. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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 / 39
    5 of 5 stars (27) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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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 VenetianTropics@aol.com for the application.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars 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...
    5 of 5 stars Reviewed 12 January 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 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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 / 21
    5 of 5 stars (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    WWW.SCHOONERHAMMOCK.COM This unique property offers : -master suite -apartment -cottage -3 full kitchens On Atlantic Ocean. Simple, sweet, and serene sanctuary. Please contact Andy Cancela 828 808 1693 We love The Lord and look forward to sharing our home with you. View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 24 October 2014
    My family/extended family stayed here in June 2012 for two weeks and it was beyond wonderful. The owner ALWAYS was quick to respond to emails even if it was to say "you're...
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    1 / 15
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
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    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This beautifully furnished and spacious... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 26 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 stars Reviewed 20 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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    1 / 25
    2 of 5 stars (1) Poor
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise in the Florida Keys! Come and relax at our beautiful ocean front home with breathtaking, panoramic views of the Atlantic ocean. This spit level home is located... View all property information
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    Islamorada, Florida Keys 33036
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on... View all property information
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    Islamorada, Florida Keys 33036
    1 / 3
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Keys Kottage Villa is located in beautiful Islamorada, Florida Keys. We are on mile marker 82. Private Marina access and trailer parking available to guests. Bring your boat and or pet. We can accommodate up to 26 ft. vessels. This is a Fisherman's dream for a week of fishing. Please call for... View all property information
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    Islamorada, Florida Keys 33036
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ower 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 sleeps up to 6 people - rent one or all... View all property information
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    Islamorada, Florida Keys 33036
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    Newly remodeled mobile home cottage is more than you've imagined so far. Enjoy the bright open living area with panoramic horizon view from the kitchen/living room. Open the 2 sets of French Doors to bring the outside, in. Sit on the wrap around deck to watch the Sun Rise out of the water, year... View all property information
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    Islamorada, Florida Keys 33036
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    MINIMUM RENTAL 1 MONTH: 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 share... View all property information
    Location Information
    Islamorada, Florida Keys
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Balcony
    • Patio
    • Terrace
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    MINIMUM RENTAL 1 MONTH: Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in this home. It is... View all property information
    Location Information
    Islamorada, Florida Keys