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Vacation Rentals in Islamorada, FL

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    Travellers to Islamorada are booking March dates now. Secure your vacation rental today, and have the perfect trip.
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    16 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Located at mile marker 76 overlooking a beautiful canal leading to the Atlantic Ocean. Boat slip available for the adventurous types. Kayaks for those wanting to explore the local mangroves. Borrow a bicycle and peddle your way through the lower matecumbe via bike path. Don't forget to visit... View all property information
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    Islamorada, Florida Keys 33036
    1 / 15
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Relax and Unwind in Your Luxuriously Renovated Condo With Oceanfront Views in the Fishing Capital of the World: Islamorada!! Beautiful Open Water Views in a Well-appointed Building That Provides Everything You Need for a Relaxing and Memorable Vacation. the Cozy Patio Invites You to Enjoy Your... View all property information
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    Islamorada, Florida Keys 33070
    1 / 29
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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
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    Islamorada, Florida Keys 33070
    1 / 22
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This relaxing private home, known as "Windley Cottage" is located in Angler's Reef, Islamorada's premier gated oceanfront community with private beaches, boat docks (available for rent), and a resort-style swimming pool overlooking the boat dock lagoon, beaches, and the Atlantic ocean.... View all property information
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    Islamorada, Florida Keys 33036
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    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
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    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 / 21
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
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    About this property
    Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new... 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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    About this property
    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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    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 / 17
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    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
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    About this property
    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
    4 of 5 bubbles (4) Very good
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
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    • x
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** This water front home is located oceanside in the tropical Lower Matecumbe key, Islamorada, mile marker 73 (The Sport Fishing Capital of the World). It features a 15' wood dock and 12’ wide ramp, so you can bring your own boat and... 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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    • x
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    About this property
    Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2 spacious... 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
    MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless steel appliances, and tray... View all property information
    Location Information
    Islamorada, Florida Keys 33036
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    1 / 38
    5 of 5 bubbles (28) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Waterfront
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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 me for the application. Weekly vacation rental... 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
    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 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of the World.' If you are looking for gold sinks, with gold fixtures, this is not the place for you! This is a place to just 'hang out' while savoring the ocean view, breezes and sounds. If you want peaceful, secluded and close to nature... View all property information
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    Islamorada, Florida Keys 33070
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Keys home in Anglers Reef with ocean view, dock, community pool & private beach This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef... View all property information
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    Islamorada, Florida Keys 33036
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    5 of 5 bubbles (4) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    • x
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    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
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    Islamorada, Florida Keys 33070
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    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 / 45
    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
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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 / 29
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Minimum Rental: 1 Month Charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. You will enjoy your stay in... View all property information
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    Islamorada, Florida Keys
    1 / 29
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully... View all property information
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    Islamorada, Florida Keys 33036
    1 / 14
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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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
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    2 of 5 bubbles (2) Poor
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    This unit's kitchen, bathrooms, windows, and doors received a facelift in January 2014! Enjoy the spectacular view of the Florida Bay from either one of the TWO balconies in this 2 story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, flat panel TV's in the... View all property information
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    Islamorada, Florida Keys 33036
    1 / 6
    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... View all property information
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    Islamorada, Florida Keys 33036
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    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
    1 / 21
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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
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    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    MINIMUM STAY: 29 DAYS Lovely condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival. Kitchen is complete with pots, pans, dishes, glasses and flatware.... View all property information
    Location Information
    Islamorada, Florida Keys
    1 / 16
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Internet Access
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 28
    5 of 5 bubbles (30) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Please contact us for all of our rates for different length of stays! For shorter stays...make sure you have a minimum of 28 days entered in your contact form! DO NOT BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you significant FlipKey booking... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 30
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Patio
    • Satellite TV
    • Balcony
    • Terrace
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 49
    5 of 5 bubbles (6) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Patio
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 6
    4 of 5 bubbles (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Grill
    • Waterfront
    • DVD Player
    • Washer
    • Balcony
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Housekeeping...
    • Balcony
    • Grill
    • Central Heating
    • Washer
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
    • Patio
    • Grill
    • Balcony
    • Terrace
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Islamorada, Florida Keys 33070
    1 / 29
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Patio
    • Shared Outdoor Pool...
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Casa Dorado is an exceptional privately owned single family home located directly on Florida Bay on Lower Matecumbe Key in Islamorada. The house is named after the owners' favorite species of fish, the Dolphinfish, also known as Dorado in Spanish speaking coastal areas. With the green roof and... View all property information
    Location Information
    Islamorada, Florida Keys
    1 / 20
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Patio
    • Parking
    • Private Outdoor...
    • Waterfront
    • Air Conditioning
    • Porch
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This is a huge 6 bedroom pool home with direct dockage just off Snake Creek. Home has 2 kings, 3 queens, and 2 twins. Located at mile marker 86 on the bay side I only take payment by personal check made out to owner!!! Never a wire transfer!!! Please be careful. This home only rents... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 35
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    This townhome at Executive Bay will sure make your home away from home!  This unit has been completely renovated and decorated beautifully.  This 2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Satellite TV
    • Patio
    • Balcony
    • Parking
    • Grill
    • Shared Outdoor Pool...
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Islamorada, Florida Keys 33036
    1 / 18
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Balcony
    • Internet Access
    • Grill
    • Parking
    • Washer
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This Property is fully insured for rentals and licensed by the Village of Islamorada, license #VR-228. Welcome to 134 Anglers, a newly renovated luxurious escape for your vacation needs. Perfect for families, couples, or a friends getaway. Located in Anglers Reef, a gated community with heated... View all property information
    Location Information
    Islamorada, Florida Keys