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Villas in Islamorada

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    Travellers to Islamorada are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    1 Bedroom, Sleeps 3Quick View
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    Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo, on mile marker 74). 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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Reviews
    5 Bedrooms, Sleeps 10Quick View
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    ***7 day minimum rental - notwithstanding anything in the rates page the MINIMUM rental is 7 days ****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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 6Quick View
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    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    24 Reviews
    2 Bedrooms, Sleeps 5Quick View
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    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    1 Review
    1 Bedroom, Sleeps 4Quick View
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    Minimum Rental: 28 Days "The Palms #417" has 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 restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    Minimum Rental: 28 Days "The Palms #407" is a 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...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    Minimum Rental: 28 Days "The Palms #506" is a 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...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, Sleeps 4Quick View
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    • Private Garden
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    Beautiful 1 BDRM apartment located in Islamorada. Full kitchen and 1 full bath. Home is located on canal within 100 yards of the ocean. You will enjoy access to fully screened and heated pool. WiFi and cable TV included. Close proximity to shopping, restaurants and all the best the Keys have to...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 6Quick View
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    Beautiful 3 bedroom 2.5 bath luxury condo at MM 74.5 Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and free Wi-Fi at community clubhouse (this unit does not have Wi-Fi inside the condo) . The condo boasts some amazing views of the Clear Blue...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Satellite TV
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    About this property
    Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. Offering Modern Granite Counter Tops and Stainless Steel Appliances. Plush...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    2 Bedrooms, Sleeps 4Quick View
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    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the "Sport Fishing Capital of the World". Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    This magnificent home with direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Lie in bed and view the Ocean! Home also overlooks the community pool. Anglers Reef is a quiet oceanfront...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,800 per...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    About this property
    Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    Minimum Rental: 28 Days "My Paradise" is an oceanfront beach house with protected dockage 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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 18Quick 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, accommodating a total of 18 people. The Upper Duplex & The...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 18
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    2 Bedrooms, Sleeps 6Quick View
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    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    Experience total seclusion in this ten-unit oceanfront complex called Port of Call, nestled along Millionaire's Row in Plantation Key, Islamorada on the Atlantic Ocean, Mile Marker 88. Outdoor facilities include a heated pool; chickee hut with common area barbecue grills, Volleyball courts on a...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Housekeeping Included
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    Pet friendly
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    Smoking allowed
    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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    2 Bedrooms, Sleeps 6Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Minimum Rental: 28 Days "The Palms #301" is an 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...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    Minimum Rental: 28 Days "Matecumbe Jewel" is a 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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    2 Bedrooms, Sleeps 6Quick View
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    • Private Outdoor Pool (Unheated)
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    • Waterfront
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    Pet friendly
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    Smoking allowed
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    Canal-front house, quiet and in the nicest of neighborhoods (Plantation Key Colony). Situated on the bayside on Mile Marker 90. All remodeled,white tiled floor, furnished in wicker/rattan and decorated with the ocean & beach ambiance in mind. Boat dockage in the back and easy access to few boat...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 8Quick View
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    • Terrace
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    Pet friendly
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    Minimum Rental: 28 Days "Manatee Manor" is a 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 to Tavernier Creek...
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    Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    28 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    • Private Outdoor Pool (Heated)
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    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 14Quick View
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    Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, Sleeps 4Quick View
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    Minimum Rental: 28 Days "The Palms #402" is a 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 the fishing boats...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    16 Bedrooms, Sleeps 11Quick View
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    • DVD Player
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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...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 16 Bedrooms, 5 Bathrooms, Sleeps 11
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    6 Reviews
    1 Bedroom, Sleeps 3Quick View
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    Minimum Rental: 7 Days "Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, Sleeps 6Quick View
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    Minimum Rental: 7 Days (Saturday to Saturday) "Brock Haus on the Gulf" is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Wonderful two story townhome in a private, gated community with all of the amenities you'd expect while on vacation. Inside: Newly renovated and remodeled unit. Fully equipped kitchen and stainless appliances, large storage cabinets with pull outs. Granite counters etc. Living room area with 60...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Review
    2 Bedrooms, Sleeps 8Quick View
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 in the Florida Keys. 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...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10Quick View
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    About this property
    WE DO NOT ACCEPT WIRE TRANSFERS AS PAYMENT...ALL PAYMENT IS THROUGH FLIPKEY Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen,...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    1 Review
    2 Bedrooms, Sleeps 5Quick View
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    Minimum Rental: 28 Days "The Palms #314" is a 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...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, Sleeps 4Quick View
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    Minimum Rental: 28 Days "Beacon Reef 501" is an 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...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, Sleeps 8Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps eight people. Master bedroom has a king bed with access to the balcony. Second bedroom has a queen bed and third one has two twin beds. TVs in every...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Terrace
    • Satellite TV
    • Parking
    • Internet Access
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 10Quick View
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    • Private Garden
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home with 3 bedrooms and 2 bathrooms,everything renovated,kitchen remodeled with stainless steels appliances ,the house have comforted beds for 10 people's ,backyard area with BBQ ,private parking inside the house for 6 cars,private ramp for boat and jetski inside the house,beautiful...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    • Internet Access
    • Waterfront
    • Air Conditioning
    • Balcony
    • Grill
    • Satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Summer Sea Luxury invites you on a breezy coastal escape to the tranquil island living of Islamorada. Welcoming up to four guests, it features resort-style amenities, including shared pools, a fitness gym, a pool table, and more. Located just off the Overseas Highway, this one-bedroom condo is...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • DVD Player
    • Satellite TV
    • Patio
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    • Internet Access
    • Air Conditioning
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit is a duplex with 2 full Bedrooms and 2 full Baths - plus a loft in the master bedroom that sleeps an additional 2. There is also an electric EZ Bed for larger groups. Also included is a gas BBQ Grill in the back porch and use of any of the recreational items at the unit. Located in the...
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    Location Information
    Islamorada, Florida Keys 34950
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex consisting of 70 units. Enjoy wonderful Bay views and sunsets from our two bedroom / two bath condominium unit that sleeps up to 6 people. Stay in...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 5Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days "West Plaza Del Lago" 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 much as the exterior! As you enter...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days "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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dubbed Aguazul, the home has four bedrooms and three bathrooms. There's also a small bungalow off the pool deck, meaning the property can comfortably sleep nine. Two separate kitchens, one on each of the home's two levels, are another unique feature. Cool off in the home's oceanfront swimming pool,...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Washer
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Grill
    • Internet Access
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Balmy weather, sunshine and a little magic await you in the Florida Keys… Look no further than this exquisite Islamorada vacation rental home as your own personal oasis during your upcoming tropical getaway! Nestled in the exclusive oceanfront gated community of Angler’s Reef in Islamorada on...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 10Quick View
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    • Internet Access
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    • Terrace
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Satellite TV
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Infinite ocean views from the large balcony at this modern and luxurious oceanfront condo at mile marker 87. BOAT SLIP INCLUDED which can accommodate up to a 30' boat. SLEEPING ARRANGEMENTS (Sleeps 4) Master Bedroom: - King Size...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    • Terrace
    • Parking
    • Satellite TV
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 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...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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