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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.
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Minimum Rental: 7 Nights 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 sleeps up... View all property information
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    Islamorada, Florida Keys 33036
    1 / 29
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Enjoy the spectacular view of the Florida Bay from this elegant, tasteful, completely remodelled townhome. 2 bedrooms, 2.5 bathrooms with balconies off the living room and master bedroom. Fully furnished and equipped for vacationers. Wifi and washer dryer in the unit. Very affordable dockage... View all property information
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    Islamorada, Florida Keys
    1 / 21
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Minimum Rental: 1 Month 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 Ocean... View all property information
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    Islamorada, Florida Keys 33036
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 33070
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Minimum Rental: 1 Month Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony. Watch... 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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    Minimum Rental: 7 Nights 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 unit... View all property information
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    Islamorada, Florida Keys 33036
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    1 / 14
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ***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
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    Islamorada, Florida Keys 33070
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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 / 17
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Minimum Rental: 1 Month 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 on a... View all property information
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    Islamorada, Florida Keys 33036
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;... View all property information
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    Islamorada, Florida Keys 33036
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Minimum Rental: 1 Month 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 bay.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    5 of 5 bubbles (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
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    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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
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    Islamorada, Florida Keys 33036
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    *** Owner is highly motivated to rent! Contact us for discounts *** Beautiful two bedroom townhouse on the Bay side with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful, newly renovated town home in the Florida... View all property information
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    Islamorada, Florida Keys 33036
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    MINIMUM STAY: 29 DAYS FISHERMANS PARADISE is this pleasing well maintained waterfront stilt home. It is conveniently located in Tavernier with easy access to the most popular restaurants, shopping and attractions in the upper Keys. The deep and wide canal makes it easy to turn your boat... View all property information
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    Islamorada, Florida Keys
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    MINIMUM STAY: 28 DAYS NEW LISTING - Available this winter! But Hurry… this home promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as... View all property information
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    Islamorada, Florida Keys
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    1 / 33
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Minimum Rental: 1 Month NEW ON THE RENTAL MARKET Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself... 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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    MINIMUM STAY 29 DAYS. -JANUARY SPECIAL - JANUARY SPECIAL - LET'S MAKE A DEAL - CONTACT US TODAY! 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... View all property information
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    Islamorada, Florida Keys 33070
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Beautiful and spacious home with three bedrooms, two and half baths, huge new kitchen, new bathrooms, and screened in porches facing East and West. There are great views from every room!!! Tastefully furnished with all linens, comfortable memory foam mattresses, all new appliances, and completely... View all property information
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    Islamorada, Florida Keys 33036
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    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the moment you... View all property information
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    Islamorada, Florida Keys 33036
    1 / 13
    16 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    About this property
    Casa Morada is an upscale sixteen suite privately owned hotel inspired by the informal character of the Caribbean. The atmosphere is private, peaceful, and serene. The staff is renowned for their warmth and attentiveness. We have 11 suites in our Garden House and 5 suites in our Seaview house. The... View all property information
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    Islamorada, Florida Keys 33036
    1 / 31
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Vacation Rental License No VR-001 Mile Marker 86 We are a licensed private pool vacation home/ deep sailboat canal and licensed to rent by the WEEK. Email me for the application at VenetianTropics ( we are not allowed to insert our email address, but you can find me on the web or simply click on... View all property information
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    Islamorada, Florida Keys 33036
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    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Minimum Rental: 7 Nights Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a full... View all property information
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    Islamorada, Florida Keys 33036
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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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 33036
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Minimum Rental: 1 Month 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 Visual... 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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    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 6 | Quick View
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    Minimum Rental: 1 Month A Diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room furnishings and the... View all property information
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    Islamorada, Florida Keys 33036
    1 / 10
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Great deep dockage and quick access to bay and ocean!!! Beach & Bay Bungalow. This home has it all. Plasma television and high speed wireless interntet included. All bedrooms have flat screen television. Spectacular long water views from inside and out of this secluded estate property! The only... View all property information
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    Islamorada, Florida Keys 33036
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    MINIMUM STAY: 29 DAYS LYONS LANDING 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 bedroom and... View all property information
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    Islamorada, Florida Keys
    1 / 21
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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
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    Islamorada, Florida Keys 33070
    1 / 29
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA View Map Accommodations: House, 3 Bedrooms, 2 Baths, sleeps 6 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three... View all property information
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    Islamorada, Florida Keys 33036
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    3 of 5 bubbles (2) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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 33036
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • x
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    • x
    About this property
    Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay.<BR><BR>Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget... View all property information
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    Islamorada, Florida Keys 33036
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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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    4 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    Live your tropical dream at this palatial oceanfront estate. Located near mile marker 89, on Islamorada's Millionaires' Row, this 4 bedroom / 6 bath home comes with just about every convenience you can imagine, as well as some you probably haven't even considered. Enjoy a swim in the pool that... View all property information
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    Islamorada, Florida Keys 33070
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • ?
    • ?
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    • x
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    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
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    Islamorada, Florida Keys 33036
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    *** Owner is highly motivated to rent! Contact us for discounts *** Welcome to our newly renovated, little slice of paradise! Come and relax at our beautiful Key Largo home, located in the Sport Fishing Capital of the World. Just minutes from John Pennekamp Park and the world famous Tiki Bar as... View all property information
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    Islamorada, Florida Keys 33036
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
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    If you’ve been to Islamorada you know it as the sportfishing capital of the world, a place where you’ll find every water-related activity imaginable, with fine restaurants to crab shacks serving local fare, and plenty of nightlife for both the young and young at heart. If you’ve never been here, a... View all property information
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    Islamorada, Florida Keys 33070
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Half Duplex Home Are you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and... View all property information
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    Islamorada, Florida Keys 33070
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This beautiful 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 33036
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    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    * 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)... View all property information
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    Islamorada, Florida Keys 33036
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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 33036
    1 / 21
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
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    • Grill
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Royal Palm, South - Ocean Front Home ( recent fraud. NEVER wire us money. Payment for reservations can only be done via the phone, not online or via wire) Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil with nothing compromised this luxurious Caribbean home... View all property information
    Location Information
    Islamorada, Florida Keys 33036