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Vacation Rentals in Islamorada, FL

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    Travellers to Islamorada are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    2 BedroomsSleeps 4Quick 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....
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Great deep dockage and quick access to bay and ocean!!! Beach & Bay Bungalow. This home has it all. Plasma television and high speed wireless interntet included. All bedrooms have flat screen television. Spectacular long water views from inside and out of this secluded estate property! The only...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Satellite TV
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    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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    4 BedroomsSleeps 8Quick 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...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    • Balcony
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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...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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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....
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 BedroomsSleeps 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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    3 BedroomsSleeps 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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    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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    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    4 BedroomsSleeps 10Quick View
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    • Private Garden
    • Wi-Fi
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    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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    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 BedroomsSleeps 8Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps eight people. Master bedroom has a king bed with access to the balcony. Second bedroom has a queen bed and third one has two twin beds. TVs in every...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 BedroomSleeps 4Quick View
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    • Patio
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    • Shared Outdoor Pool (Unheated)
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Minimum Rental: 28 Days "Beacon Reef 310" 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 relaxing on your own...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
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    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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    2 BedroomsSleeps 6Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    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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    • Shared Outdoor Pool (Unheated)
    • Patio
    • Terrace
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    • Satellite TV
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    Pet friendly
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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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    2 BedroomsSleeps 6Quick View
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    • Shared Outdoor Pool (Unheated)
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    Minimum Rental: 28 Days "The Palms #405" is a diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living room...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 BedroomSleeps 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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    • Central Heating
    • Terrace
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    Pet friendly
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    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?...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
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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 BedroomsSleeps 8Quick View
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Welcome to our newly renovated, little slice of paradise! Come and relax at our beautiful Key Largo home, located on mile marker 87 in the Sport Fishing Capital of the World. Just minutes from John Pennekamp Park and the world...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 BedroomsSleeps 10Quick View
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    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 BedroomsSleeps 6Quick 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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    16 BedroomsSleeps 11Quick 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...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 16 Bedrooms, 5 Bathrooms, Sleeps 11
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    About this property
    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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    2 BedroomsSleeps 6Quick View
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    Smoking allowed
    About this property
    Enjoy the spectacular view of the Florida Bay from this elegant, tasteful, completely remodelled townhome. 2 bedrooms, 2.5 bathrooms with balconies off the living room and master bedroom. Fully furnished and equipped for vacationers. Wifi and washer dryer in the unit. Very affordable dockage...
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    Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 BedroomsSleeps 6Quick 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...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    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...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    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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    About this property
    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 BedroomsSleeps 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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    • Internet Access
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    • Private Outdoor Pool (Heated)
    • Waterfront
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    Kid friendly
    Smoking allowed
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    WE DO NOT ACCEPT WIRE TRANSFERS AS PAYMENT...ALL PAYMENT IS THROUGH FLIPKEY Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen,...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    • Sauna
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    Kid friendly
    Smoking allowed
    About this property
    Savor a sun-filled vacation in this charming oceanfront condo, complete with sweeping ocean views and shared amenities such as a gym, saunas, a pool, tennis courts, laundry facilities, barbecues, and a party room. In the Sea Gull Condos complex, this rental is less than one mile off Old Highway 1...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Kid friendly
    Smoking allowed
    About this property
    Park Model mobile home located oceanside on beautiful Windley Key in Islamorada, Florida Keys, the 'sport fishing capital of the world.' This is a great spot for relaxing, fishing and/or exploring the Keys, situated 75 miles from Miami and 85 miles from Key West. 1 BR plus upstairs sleeping or...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    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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    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 28
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Smoking allowed
    About this property
    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    • DVD Player
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    License #: VR-215, DWE5403682 This resort style community is located at mile marker 85 in Islamorada and is situated directly on the Atlantic Ocean with fantastic views. The community is beautifully landscaped and has a large community pool (heated year-round) that overlooks the ocean! The...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    3 BedroomsSleeps 8Quick View
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    • DVD Player
    • Internet Access
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    • Washer
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    • Ocean Views
    • DVD Player
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 BedroomsSleeps 6Quick View
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    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Balcony
    • Parking
    • Terrace
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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