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Villas and Holiday Rentals in Islamorada, FL

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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 45
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    * 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 13
    4.5 of 5 stars (16) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please send us an inquiry or call us for availability. We have a couple of units. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool, sandy beachy area, and fishing pier with flats boat dockage (drawing 24" or less) located directly on the ocean.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 30
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    <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
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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
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 stars (6) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club... View all property information
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    Islamorada, Florida Keys 33036
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to Modern Keys Living with Bay Views! New from top to bottom!!! Newly remodeled and beautifully decorated 1st floor corner unit with a private entrance. Enjoy the mix of vintage and new furniture and the most comfortable sofas, beds, linens and more! This home is equipped with everything... View all property information
    Location Information
    Islamorada, Florida Keys 33070
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    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two... View all property information
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    Islamorada, Florida Keys 33036
    1 / 29
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    <b>Casa Dorado</b> 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... View all property information
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    Islamorada, Florida Keys
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    <b> Minimum Rental: 1 Month </b> 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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 12
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    <b> Minimum Rental: 1 Month </b> Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina. You'll be able to see cruise ships as they pass by Alligator... View all property information
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    Islamorada, Florida Keys 33036
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This oceanfront resort is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture built in 2007. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located on the peaceful, northern end of Islamorada, in the quite residential neighborhood of Venetian Shores. Just 75 miles from Miami Airport and 86 miles from Key West. Venetian Tropics boasts large rooms furnished in rattan and decorated with a tropical flair. Coconut palms, hibiscus and other... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    <b>Monthly Rental: </b> 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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Two Oceanfront villas on two beautiful acres. It has a total of three bedrooms and two and half baths. Sleeps 8-10 comfortably. One King bed, two queen beds, two twin beds, and two queen size pull out sofas. Both villas have full kitchens, living area, lots of windows with gorgeous Ocean and beach... View all property information
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    Islamorada, Florida Keys 33036
    1 / 39
    5 of 5 stars (27) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email VenetianTropics@aol.com for the application.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 18
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    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
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    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 / 49
    5 of 5 stars (14) Excellent
    10 Bedrooms, 10 Bathrooms, Sleeps 20 | Quick View
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    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
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    Islamorada, Florida Keys 33036
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    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This home is located in a nice, quiet family neighborhood at the 90 mile marker (90 miles from Key West), Bayside. The house sits on the last canal of the neighborhood...very short boat ride to the bay (only a minute or so). Deep water dockage - 65' of dock space. There is an downstairs fully... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 38
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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 / 29
    5 of 5 stars (22) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    About this property
    House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich... View all property information
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    Islamorada, Florida Keys 33036
    1 / 10
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Private Garden
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    About this property
    Tarpon House at Bonefish Bay is one of 12 homes located in Islamorada's premier gated community. Each home features a private pool and hot tub, and guests are welcome to enjoy the common amenities such as beach, tennis court and playground. The house comes with kayak, paddleboard, and bicycles.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 27
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this... View all property information
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    Islamorada, Florida Keys 33036
    1 / 40
    4.5 of 5 stars (8) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Amazing ocean views can be enjoyed from this beautiful stilt home with seperate mother-in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile... View all property information
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    Islamorada, Florida Keys 33036
    1 / 20
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    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
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    Islamorada, Florida Keys 33036
    1 / 27
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys
    1 / 36
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Please send us an inquiry or call us for availability. Prices vary on the units. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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 / 24
    4.5 of 5 stars (7) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. VACATION RENTAL LICENSE: VR-039 CLICK HERE to view photos on a mobile device.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 12
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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, accommodating a total of 18 people. The Upper Duplex &... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Wake up every morning and walk right out to your private wrap deck and relax with the sound of the ocean right under your feet. We have a beautifully decorated and updated one bedroom trailer. Kick back in a open concept living room and kitchen with all new appliances. and with stunning views.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Rental amount includes all fees boat dock fee.. This newly renovated modern 4th floor condo in a private gated community has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened in Lanai, 2 lighted tennis courts, and... View all property information
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    Islamorada, Florida Keys 33036
    1 / 21
    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 / 6
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • 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
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    5 of 5 stars (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    1 / 70
    5 of 5 stars (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • x
    About this property
    Live your tropical dream at this palatial oceanfront estate that is newly available through Freewheeler Vacations. 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... View all property information
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    Islamorada, Florida Keys 33070
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This delightful 2 bedroom, 2 bathroom home is located in Port Antigua (south Islamorada) at the 74 mile marker. While not located directly on the bay, you'll still be able enjoy the homeowners park that has a beach and beautiful sunsets. The home comes equipped with Wi-Fi internet. Click here to... View all property information
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    Islamorada, Florida Keys 33036
    1 / 35
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • ?
    • x
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    • x
    About this property
    Prestigious Venetian Shores subdivision in Islamorada! This vacation home has 5 bedrooms and 3 bathrooms with 100 concrete dock. The house is situated into two separate living quarters. Upstairs is a large master suite and 2 guest bedrooms, cathedral ceilings & fully stocked, eat-in kitchen,... 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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    • Hot Tub
    • Shared Outdoor Pool...
    • Satellite TV
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • 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
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    Islamorada, Florida Keys
    1 / 20
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • ?
    About this property
    An adorable studio apartment that is perfect for one or two people. The unit is decorated nicely and has everything you need for your get away. Summer Seas is located at mile marker 88.5 on the bay side. The complex has a pool, jacuzzi, pool table room, and a game room. Inquire to see if your... View all property information
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    Islamorada, Florida Keys 33070
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Oceanfront splendor on the Atlantic ocean. Has a 350' pier that can accomodate most any size boat. Just relax by the pool on those hot days or take a dip in the ocean. The pool is heated for the winter months. The house is extremely private. There is a wooden fence around the house and... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 34
    3.5 of 5 stars (2) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    How about sipping coffee and watching the sun come up as you fish off the end of your very own 300 foot pier? Sounds good, right? Well, that's just one reason to stage your upcoming vacation at this lovely, hacienda-style home on a quaint and private oceanfront street in Islamorada. CLICK HERE to... View all property information
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    Islamorada, Florida Keys 33036
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Corner lot, Clear and deep waterways, 3 bedrms, 3 bath, sleeps 8+ Granit Tops This home is located in a prime neighborhood with 150lf of seawall for all your water toys. 3 bedrooms, 3 full bath ,1 king, 2 queens and bunkbeds, Laundry room, Wet bar, Library/Sitting room, Living /Family room and... View all property information
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    Islamorada, Florida Keys 33036
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Grill
    • Sauna
    • Internet Access
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A Vacation Rental for View Lovers! Best Location in the Complex. Peaceful, clean vacation rental with panoramic ocean views from living/dining/kitchen areas. Full Ocean View from Bedrooms! Large HDTV with preferred cable channels in living room and flat screen TV in each bedroom, ceiling... View all property information
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    Islamorada, Florida Keys 33070
    1 / 32
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This is a great 1 bedroom and 1 bathroom at the Sea Gulls Complex. This unit is located on the 6th floor and has amazing views. This unit is a decorated nicely and will be a perfect home away from home. The complex is located at mile marker 90 and has a pool and a kayak ramp. Sea Gulls Complex... View all property information
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    Islamorada, Florida Keys 33070
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Patio
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    MINIMUM STAY: 28 DAYS <b>NEW LISTING - Available this winter!</b> 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... View all property information
    Location Information
    Islamorada, Florida Keys