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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 / 29
    5 of 5 bubbles (24) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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... View all property information
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    Islamorada, Florida Keys 33036
    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
    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    MINIMUM STAY: 29 DAYS - Available this winter! Very comfortable 50ft dock, wide canal, home located close to Tavernier Creek Channel with easy access to the Gulf and Atlantic. Great fishing, kayaking and diving. Concrete dock, fish cleaning station . 1.5 mile north of the world famous Holiday... View all property information
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    Islamorada, Florida Keys 33070
    1 / 29
    5 of 5 bubbles (3) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick 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... 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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    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... View all property information
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    Islamorada, Florida Keys 34950
    1 / 23
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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... View all property information
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    Islamorada, Florida Keys 33070
    1 / 25
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys 33036
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    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick 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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    5 of 5 bubbles (6) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick 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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 27
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Private Garden
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    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... 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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    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys
    1 / 26
    4 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Private Garden
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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
    1 / 24
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Minimum Rental: 28 Days "The Palms #214" is a gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick 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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 17
    5 Bedrooms, 6 Bathrooms, Sleeps 18 | 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, accommodating a total of 18 people. The Upper Duplex & The... View all property information
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    Islamorada, Florida Keys 33036
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    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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... View all property information
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    Islamorada, Florida Keys
    1 / 68
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    ***** Amazing Home For An Amazing Price Through January 31st, 2017 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... View all property information
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    Islamorada, Florida Keys 33070
    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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    • 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
    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick 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... View all property information
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    Islamorada, Florida Keys 33070
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick 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... 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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    About this property
    Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium complex with heated out door pool, gym, plenty of parking, secured entrances, elevator, and quiet. My condo is kept meticulously with attention to detail. Linens, towels and pool towels are included in the... View all property information
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    Islamorada, Florida Keys 33070
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick 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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 27
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys 33070
    1 / 49
    5 of 5 bubbles (6) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick 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... 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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    • x
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    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... 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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    • x
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    • x
    About this property
    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys 33036
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Minimum Rental: 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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Minimum Rental: 28 Days "Beacon Reef 222" is an 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.... View all property information
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    Islamorada, Florida Keys 33036
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 27
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    Escape to your own Bayside Vacation Villa in Islamorada. We offer brand new 3 bedroom, 3.5 bathroom villas in the Islamorada Art District on the Florida Bay. These Bayside villa rentals are located closest to the pool, dock and fresh, clear bay waters. The villas are very near our iconic marinas... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    3.5 of 5 bubbles (2) Average
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
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    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • ?
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    • x
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    Vacation Rental License No VR-001 Mile Marker 86 We are a licensed private pool vacation home/ deep sailboat canal and licensed to rent by the WEEK. Email me for the application at VenetianTropics ( we are not allowed to insert our email address, but you can find me on the web or simply click on... View all property information
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    Islamorada, Florida Keys 33036
    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • DVD Player
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    • Washer
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
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    Islamorada, Florida Keys 33036
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Washer
    • Balcony
    • Ocean Views
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 15
    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    This home features 4 bedrooms, 2 baths, pool and bar. This home can comfortably accommodate 8-10 people with room to spare. Alluring turquoise ocean and beachfront views. The onsite boat parking provided tremendous privacy and space for you and all of your guest. A private pool and grill that... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 25
    3 of 5 bubbles (2) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • DVD Player
    • Patio
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 9
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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... View all property information
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    Islamorada, Florida Keys 33070
    1 / 34
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • DVD Player
    • Waterfront
    • Private Outdoor...
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    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 26
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Internet Access
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    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 25
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Balcony
    • Parking
    • Terrace
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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... View all property information
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    Islamorada, Florida Keys 33070
    1 / 25
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Grill
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    • Patio
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    • Balcony
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
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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... View all property information
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    Islamorada, Florida Keys 33036
    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Central Heating
    • Terrace
    • DVD Player
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    • Sauna
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    ****Recently updated paint, furniture and a Beauty Rest Mattress!!**** Looking to escape reality? Look no further! Spacious 1 bedroom/1 bathroom condo located in the newly renovated Summer Seas Condominiums. Sit back and relax at the pool, go swimming at the private beach. Feeling adventurous?... View all property information
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    Islamorada, Florida Keys 33070
    1 / 28
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • ?
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    Escape to your own Bayside Vacation Villa in Islamorada. We offer brand new 3 bedroom, 3.5 bathroom villas in the Islamorada Art District on the Florida Bay. These Bayside villa rentals are located closest to the pool, dock and fresh, clear bay waters. The villas are very near our iconic marinas... View all property information
    Location Information
    Islamorada, Florida Keys 33036