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Islamorada Vacation Rentals

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    Travellers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    BEACON REEF 2221 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Islamorada cottage on deep water canal1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    About this property
    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Ocean-Front Caribbean Home.1 / 21
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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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...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Cottage is a bright and airy 1,250 sq ft unit with a huge...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
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    About this property
    Tropical weather, sunshine, and a little magic await you in the Florida Keys! Look no further than this exquisite Islamorada vacation rental home as your personal oasis during your upcoming tropical getaway. This 2-bedroom, 2 and a half bathroom island home sleeps 6 in a personal paradise. Nestled...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    LITTLE BAY - Cottage1 / 24
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Minimum Rental: 7 Days "Little Bay's Cottage" 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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    OCEANFRONT pool30'DockGatedPrivate7niteMin6ppl max1 / 49
    (6)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    FOR ADDITIONAL REVIEWS GO TO "HOMEAWAY.COM" LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS IF YOU GET A RESPONSE FROM BESTHOLIDAYRENTALS.COM **** IGNORE IT **** SCAM MINIMUM STAY 7 NIGHTS, MAXIMUM OCCUPANCY 6 PPL, NO PETS, RENTAL...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    2 BR 2 BA 1 HF BA Sleeps 8 There is no other neighborhood like Anglers Reef in Islamorada. It's beautiful Key West style pastel colored homes inside resort community, with garden like flora and fauna such as bougainvillea meticulously maintained, with a fantastic oceanfront swimming pool and boat...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    • Private Outdoor Pool (Heated)
    • Waterfront
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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,...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Islamorada Oceanfront Pool home! Wake up in the morning to a gorgeous sunrise.  This home is a 3 bedroom 2 bath home with vaulted wood ceilings, decorated with a cottage feel.  The porch is perfectly shaded and overlooking the Atlantic Ocean. Relax in the heated swimming pool or swing in the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Lower Duplex is a 1,500 sq ft unit with 2 bedrooms, 2 full...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfect catch and enjoy a sunset...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • DVD Player
    • Waterfront
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Welcome to paradise! Built in 2012 and designed by well-known Miami architect to mirror the curved shoreline of the beach, this private custom contemporary beach home is a one of a kind, unique design with gated entry, large private beach, and gorgeous ocean views from every room. Built using ICF...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Oceanfront Luxury Islamorada Estate - 4 bed/pool1 / 63
    (2)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Waterfront
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    • Ocean Views
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    Pet friendly
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    Smoking allowed
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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)...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
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    Smoking allowed
    About this property
    Minimum Rental: 7 Days Little Bay's Upper Duplex 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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage....
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Islamorada 2-bedroom Condo1 / 6
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    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...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mina Bay - Oceanfront "Million Dollar View"1 / 19
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Mina Bay - vacation rental with "the million dollar view"! Truly OCEANFRONT on the sandy beach and feet from the pier and dock. Sparkling water's and brilliant sunsets complete this 2 Bd 1.5 Ba plus loft Unit I-1 townhouse. 28 DAY MIMIMUM RENTAL for all guests.  Accommodates a family of 8 perfectly...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Southern Diversion Islamorada see our fall special1 / 30
    (7)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Porch
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    • Outdoor Dining Area
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    About this property
    This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat lift, Tiki hut on private beach, Heated pool and Wireless remote Internet. Southern Diversion has just been completely renovated. Brand new...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Weekend Getaway!!! Enjoy the most beautiful sunsets on earth from this gorgeous 4 bedroom, 5 bathroom plus casita, tropical paradise. There are two master suites, one entry level (no stairs) and one on third floor, both with amazing views. Comes complete with Bayfront pool and lounge area that will...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Beautiful 2 bedroom 2 bath, condo with everything that you need for a perfect relaxing vacation. Balcony access off your living room and master bedroom that overlooks the newly remodeled pool and jacuzzi as well as the beach and ocean. The complex is oceanfront and this unit has ocean views. Some...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 MINIMUM STAY REQUIRED - NOT A SHORT TERM RENTAL - PLEASE CONTACT US FOR SPECIFIC DATES, AVAILABILITY AND RATES. Every time we stay, we never want to leave. 3 story bayside villa with its own beach. Great location. Views of both the Bay and the Ocean. Three good...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Hot Tub
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    LITTLE BAY - Lower Duplex1 / 23
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Minimum Rental: 7 Days Little Bay's Lower Duplex 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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    BEAUTIFUL BAYFRONT HOME WITH SUNSETS FROM EVERY ROOM BRAND NEW FURNITURE! Fish the backcountry or the Ocean, just minutes away. House has 3 bedroom suites with king beds in every room. Deep water dockage, capable of handling large boats. 100' dock. Very private quiet area. Home has 52" TV in...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Looking for an amazing home in Venetian Shores?  This home has everything - 4 bedroom, 4 bath home that has been updated.  The kitchen is amazing, suited for any type of entertaining.  The 3rd floor floor is a lofted master bedroom suite with a walk-in closet.  Two guest bedrooms are located on the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Park Model mobile home located oceanside on beautiful Windley Key in Islamorada, Florida Keys, the 'sport fishing capital of the world.' This is a great spot for relaxing, fishing and/or exploring the Keys, situated 75 miles from Miami and 85 miles from Key West. 1 BR plus upstairs sleeping or...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Balcony
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    About this property
    Highend remodeled and luxuriously furnished bay view condo in the gated community of Futura Yacht Club. 2 bedroom 2 full bath Condo with a open den that can be closed off as a third room (queen size murphy bed). Flat screen tv in every room with cable and wifi. Gorgeous modern kitchen with eat in...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Children's Pool
    • Washer
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    • Waterfront
    • Satellite TV
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very large, Islamorada, waterfront, pool home with plenty of room for everyone on Lower Matecumbe Key in the heart of the Florida Keys. The house has a total of 10 beds in 7 bedrooms and comfortably sleeps 14 guests. The house is 3 stories, with an elevator, and has over 4,200 air-conditioned...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Washer
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise! This home is a new listing to Flip Key. If you are looking for a large beautiful home with a pool in a peaceful setting and in an absolutely perfect location for your stay in Islamorada, you have found it! We are located in Venetian shores off Snake Creek with a boat slip for...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    • Waterfront
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS HOME ONLY OFFERS MONTHLY RENTALS. Islamorada is known as the 'Sport Fishing Capital of the World.' This property is located just minutes from the Atlantic Ocean, where you can head off shore to the Gulf Stream and reel in the big game, or travel into the Florida Bay, where you will find vast...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    The PERFECT Escape with pool & jacuzzi1 / 9
    (7)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful 4 bedroom/ 4 bathroom home has a 60' dock directly behind the home . Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Florida Keys- Venetian Shores. Upstairs there are 2 bedrooms/ 2 baths and there...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Paradise and Enjoy it with Comfort! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Seaside Sanctuary 5 bedroom 5 bath pool home1 / 24
    (12)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Waterfront
    • Ocean Views
    • Washer
    • Air Conditioning
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
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    Elegant Bayfront Townhouse with boat slip1 / 27
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Patio
    • Waterfront
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    16 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • DVD Player
    • Housekeeping Included
    • Ocean Views
    • Internet Access
    • Patio
    • Air Conditioning
    • Satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 16 Bedrooms, 5 Bathrooms, Sleeps 11
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