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Pet Friendly Rentals in Islamorada, FL

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    1 / 24
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 9
    5 of 5 bubbles (3) Excellent
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    Private Room, 1 Bathroom, Sleeps 3 | Quick View
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    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
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    Islamorada, Florida Keys 33036
    1 / 40
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
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    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
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    Islamorada, Florida Keys FL 33036
    5 of 5 bubbles Reviewed February 2, 2016
    We loved our stay at Ocean Harbour Apartments. After viewing photos on your website, we chose this based on the beautiful grounds and lovely accomodations. We could not have...
    5 of 5 bubbles Reviewed January 5, 2015
    This spacious condo is beautifully furnished and equipped. The gated community is very quiet and has a heated salt water pool. There is a nice spot to see the moon and sunrise...
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    1 / 4
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Enter through a private garden with a tropical atmosphere to a quiet and secluded room with a queen size bed and a private bath. The room is completely private and features a coffee maker, microwave, refrigerator, TV and free WiFi. Full breakfast.LOCATED IN A QUIET,SECLUDED , TROPICAL SETTING YET... View all property information
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    Islamorada, Florida Keys 33036
    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • Private Yard
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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 / 7
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    A small stand alone room in the corner of the garden. Features a/c, coffee maker, free WiFi, grill on premises, heat, microwave, refrigerator, shared bathroom with one other couple, TV and includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO FISHING, DIVING,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Canal-front house, quiet and in the nicest of neighborhoods (Plantation Key Colony). Situated on the bayside on Mile Marker 90. All remodeled,white tiled floor, furnished in wicker/rattan and decorated with the ocean & beach ambiance in mind. Boat dockage in the back and easy access to few boat... View all property information
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    Islamorada, Florida Keys 33070
    1 / 19
    5 of 5 bubbles (6) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • ?
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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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed May 13, 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 February 8, 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 / 10
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | 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 / 30
    5 of 5 bubbles (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 bubbles Reviewed July 2, 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 bubbles Reviewed November 5, 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 / 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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    • ?
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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 bubbles Reviewed September 19, 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 March 28, 2016
    This is my fourth year at the property and it has only gotten better. There were some criticism of the deck conditions and lack of refrigerator at the outside Tiki hut. Those...
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    1 / 27
    5 of 5 bubbles (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 / 33
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    WE DO NOT ACCEPT WIRE TRANSFERS AS PAYMENT...ALL PAYMENT IS THROUGH FLIPKEY Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    • x
    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 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Ocean Views
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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 / 45
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • x
    About this property
    * 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 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Shared Outdoor Pool...
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    • x
    About this property
    <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 / 17
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • ?
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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
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    1 / 23
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed August 13, 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 / 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
    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    MINIMUM STAY 29 DAYS. -JANUARY SPECIAL - $500 RENT DISCOUNT - BOOK NOW! 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,... View all property information
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    Islamorada, Florida Keys 33070
    1 / 21
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    • Waterfront
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    • Pet-friendly
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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 bubbles Reviewed October 23, 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 bubbles (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    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
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed March 25, 2015
    Great property! Very beautifully decorated. I loved the view, really enjoyed my stay! I look forward to staying there again soon!
    5 of 5 bubbles Reviewed January 19, 2015
    This condo is beautifully decorated and chock full of everything you need to make your stay just perfect. The condo and the complex are extremely well maintained and have the...
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    1 / 23
    3.5 of 5 bubbles (2) Average
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    About this property
    <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 / 25
    3 of 5 bubbles (2) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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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
    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 bubbles Reviewed 5 weeks ago
    Had a wonderful time beach just out front and did a lot "beaching". Close to a nice supermarket and rental places. Will definitely be back! Thanks for a great get away!
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    1 / 49
    5 of 5 bubbles (14) Excellent
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Got a large group that wants to "get away from it all"? Or do you need lots of space for a family reunion or wedding? This is the perfect solution! Terrific location, beautiful view, two private pools for you to enjoy... And since it's 4 separate homes, you aren't right on top of each other. Wide... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles Reviewed April 13, 2016
    Three families (total of 12 people, teenagers to parents in the 50's) occupied one three bedroom and one two bedroom. The homes and furnishings were in decent shape but some...
    5 of 5 bubbles Reviewed March 7, 2015
    Great location. Very clean and relaxing. If you are looking for a waterfront view, this place does not have it but it is only a very short walk down to the dock to have a...
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    1 / 15
    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 / 4
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Smoking allowed
    • 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 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    *** Owner is highly motivated to rent! Currently we have January 2017 on Promotion. Contact us for discounts *** Infinite ocean views, breezy sunsets and the soothing sound of swaying palms is the tip of the iceberg at this spacious, modern and luxurious oceanfront condo in the Keys. SLEEPING... View all property information
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    Islamorada, Florida Keys 33036
    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    '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 / 29
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This Oceanfront splendor on the Atlantic ocean has a weekly vacation rental license, which allows for weekly rentals. There is a 350' pier that you can fish off of or simply jump in the ocean. The dock can accommodate most size boats if you wish to bring one. Just relax by the pool on those... View all property information
    Location Information
    Islamorada, Florida Keys 33070
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    5 of 5 bubbles (4) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    • Waterfront
    • Satellite TV
    • Patio
    • Air Conditioning
    • Private Outdoor...
    • DVD Player
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This impressive home is located in Islamorada on a private lagoon with quick direct access to the Florida Bay. Featuring 5 bedrooms and 5 bathrooms, this private residence offers plenty of balconies for water viewing, expansive cathedral ceilings, top of the line appliances and ceiling fans... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 bubbles Reviewed 1 week ago
    This house was perfect for our group of ten family members. It has everything you would need to make a perfect vacation. The views were amazing; the game room and pool kept all...
    4 of 5 bubbles Reviewed August 22, 2016
    The title says nice house for family reunion, it is nice, not much more. The place is outdated, not everything works, loose tiles, broken BBQ, sliding glass doors that do not...
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    1 / 28
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Internet Access
    • Grill
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Vacation Rental License No VR-001 Mile Marker 86 We are a licensed private pool vacation home allowed to rent by the week. 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.... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Balcony
    • Porch
    • Internet Access
    • Patio
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 16
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Porch
    • Air Conditioning
    • Washer
    • Grill
    • Internet Access
    • Satellite TV
    • Balcony
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Islamorada, Florida Keys
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Balcony
    • Washer
    • Terrace
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Balcony
    • Grill
    • Air Conditioning
    • Washer
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Parking
    • Satellite TV
    • Air Conditioning
    • Washer
    • Internet Access
    • DVD Player
    • Balcony
    • Terrace
    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