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Holiday Rentals in Islamorada, FL

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    $10,461
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    1 / 9
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    $6,277
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    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2
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    1 / 11
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    About this property
    ****This house cannot rent for less than 28 days, per County Ordinance**** Latitude: Freedom of thought or action. No word could better described this Keys Vacation Home. Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool. Latitude boasts 2 master suits and... View all property information
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    Islamorada, Florida Keys 33036
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    $6,137
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    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Patio
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    • Gym
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    About this property
    Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2... View all property information
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    Islamorada, Florida Keys 33036
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6
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    • DVD Player
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    ****DUE TO A COUNTY ORDINANCE THIS PROPERTY CANNOT RENT FOR LESS THAN 28 DAYS**** You fall in love with The Cottage at first sight. Built in 1935, this once Red Cross building serves as a true historical reflection of the Florida Keys. Both bedrooms overlook the ocean, which is a mere 30 feet from... View all property information
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    Islamorada, Florida Keys 33063
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    1 / 12
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Boat Available
    • Internet Access
    • Deck
    • Water Views
    • Waterfront
    • Satellite TV
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Elder access
    • x
    About this property
    ****This house cannot rent for less than 28 days, per County Ordinance**** Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Oasis. Oasis is located at Mile Marker 75.6, in beautiful Islamorada. This Beautiful three bedroom, three bath home will sleep 8 people very Comfortably. Besides the... View all property information
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    Islamorada, Florida Keys 33036
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    1 / 8
    3 of 5 stars (1) Average
    3 Bedrooms, 4 Bathrooms, Sleeps 6
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    • Washer
    • Internet Access
    • Air Conditioning
    • Water Views
    • Dryer
    • Waterfront
    • Grill
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    • Pet-friendly
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    • Child-friendly
    • ?
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    • Elder access
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    About this property
    VR-203 You can not rent this property for less than one week. Relax and rejuvenate at The Palms. Features are a plantation-style home and beautiful wrap around porch, 3 bedrooms/3.5 baths, a beach entry pool, and abundant coquina decking. The natural landscaping enhances the amazing grounds and... View all property information
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    Islamorada, Florida Keys 33063
    From
    $12,483
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    1 / 13
    5 Bedrooms, 7 Bathrooms, Sleeps 10
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    • Water Views
    • Hot Tub
    • Private Outdoor...
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Waterfront
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    You can not rent this property for less than one week. The ultimate island experience awaits you at Kara-Pan I. This exquisite, private, two story, Plantation Style home is located on a pristine natural white sand beach with oceanviews that inspire relaxation. The 5 bedroom 7 bath home with a wrap... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    $4,184
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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Ceiling Fans
    • Balcony
    • Internet Access
    • Terrace
    • Parking
    • Satellite TV
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    MINIMUM STAY: 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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    Location Information
    Islamorada, Florida Keys 33036
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    From
    $7,671
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    1 / 14
    4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Hot Tub
    • Air Conditioning
    • Waterfront
    • Private Outdoor...
    • Water Views
    • Internet Access
    • Satellite TV
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • x
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    About this property
    You can not rent this property for less than one week.The Gardens is a 4/4 private home surrounded by impeccably landscaped grounds. This property has over 50 types of palms, abundant orchids, and bougainvilleas. At your doorstep is a breathtaking view of the Atlantic Ocean where you can... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $8,369
    / Week
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    1 / 22
    5 Bedrooms, 5 Bathrooms, Sleeps 10
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    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    • Waterfront
    • Deck
    • Water Views
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Village Permit # VR-204You can not rent this property for less than one week.Sit back, relax, a light breeze, gaze the blue waters of the Atlantic Ocean….and be lost. Southern Comfort is the perfect vacation home in the Florida Keys, located at MM 77. This very private Estate sits on 3+ acres... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $27,757
    / Month
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    1 / 15
    5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Overview
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    • Waterfront
    • Internet Access
    • Water Views
    • Deck
    • Satellite TV
    • Shared Outdoor Pool...
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ****This house cannot rent for less than 28 days, per County Ordinance**** Breathtaking Sunset's, Breathtaking Home. Pineapple Plantation is an unbelievable gated, New Bay Front home. It is perfectly located a Mile Marker 89, Islamorada. Boasting 5 Bedroom Suite's, Gourmet kitchen with an ocean... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,487
    / Week
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    1 / 12
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Satellite TV
    • Water Views
    • Washer
    • Dryer
    • Internet Access
    • Waterfront
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Village Permit #VR-09-82 You can not rent this property for less than one week. Ahhhh...Ocean Front....Protected Dockage... Blue Harbor is located at Mile Marker 85, in beautiful Islamorada. This Ocean Front four bedroom,three bath home will sleep 8 people very comfortably. (One of the bedrooms is... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $5,300
    / Month
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    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview
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    • Satellite TV
    • Shared Outdoor Pool...
    • Gym
    • Balcony
    • Internet Access
    • Patio
    • Refrigerator
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm and inviting... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $1,451
    / Week
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    1 / 19
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3
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    • Ceiling Fans
    • Satellite TV
    • Grill
    • Internet Access
    • Refrigerator
    • Parking
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights You can have it all – 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 treasure... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $7,323
    / Month
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    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Balcony
    • Patio
    • Refrigerator
    • Grill
    • Shared Outdoor Pool...
    • Internet Access
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally 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 every room in this... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,487
    / Week
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    1 / 27
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (4) Make Enquiry
    Overview Reviews (4)
    Amenities & Details
    • Patio
    • Water Views
    • Grill
    • Satellite TV
    • Parking
    • Refrigerator
    • Internet Access
    • Ceiling Fans
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights Lower 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. The units are available for rent by the week, or month. Each unit... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,487
    / Week
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    1 / 31
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    Amenities & Details
    • Refrigerator
    • Balcony
    • Water Views
    • Internet Access
    • Satellite TV
    • Grill
    • Patio
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $4,463
    / Month
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    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Overview
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    • Shared Outdoor Pool...
    • Gym
    • Satellite TV
    • Internet Access
    • Refrigerator
    • Water Views
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless steel appliances, and tray... View all property information
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    Islamorada, Florida Keys 33036
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    From
    $3,208
    / Month
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    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Gym
    • Water Views
    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Hot Tub
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month 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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    Location Information
    Islamorada, Florida Keys 33036
    From
    $1,743
    / Week
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    1 / 24
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview Reviews (4)
    Amenities & Details
    • Satellite TV
    • Water Views
    • Shared Outdoor Pool...
    • Grill
    • Refrigerator
    • Balcony
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights (Saturday to Saturday) BROCKHAUS 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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    Location Information
    Islamorada, Florida Keys 33070
    From
    $5,579
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    1 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Grill
    • Ceiling Fans
    • Patio
    • Refrigerator
    • Internet Access
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. It is located... View all property information
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    Islamorada, Florida Keys 33036
    From
    $9,066
    / Month
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    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview Reviews (1)
    Amenities & Details
    • Refrigerator
    • Internet Access
    • Parking
    • Terrace
    • Grill
    • Balcony
    • Water Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $5,579
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    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Overview
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    • Patio
    • Satellite TV
    • Water Views
    • Shared Outdoor Pool...
    • Grill
    • Internet Access
    • Hot Tub
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the heart of Islamorada. This unit provides spectacular ocean views. It is one of the few units that offer spiral stairs to the ground level directly from... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $4,045
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    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview
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    • Shared Outdoor Pool...
    • Hot Tub
    • Gym
    • Satellite TV
    • Internet Access
    • Refrigerator
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month 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 furnishings and the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $6,974
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Overview
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    • Internet Access
    • Hot Tub
    • Grill
    • Refrigerator
    • Gym
    • Shared Outdoor Pool...
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Minimum Rental: 1 Month New on the rental market. This is your opportunity to secure your winter getaway at a luxurious oceanfront condo in one of Islamorada's most prestigious condominium communities. Ocean front dockage is available for boats up to 28' in length (separate rental); heated... View all property information
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    Location Information
    Islamorada, Florida Keys 87851
    From
    $2,929
    / Month
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    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview
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    • Grill
    • Water Views
    • Gym
    • Patio
    • Satellite TV
    • Shared Outdoor Pool...
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Minimum Rental: 1 Month This 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 at the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,208
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Overview
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    • Satellite TV
    • Hot Tub
    • Shared Outdoor Pool...
    • Patio
    • Grill
    • Gym
    • Refrigerator
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $16,738
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    1 / 1
    4.5 of 5 stars (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Waterfront
    • Water Views
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    One of a kind bay front estate! This is an absolutely gorgeous estate home offering a gated entrance paved brick driveway, 3,500 sf, 3 bedrooms, 3.5 bathrooms upstars and a bonus 1 bedroom, 1 bathroom apartment downstairs. Enjoy ocean & lagoon views, deep water protected dockage, 2 Great rooms,... View all property information
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    Location Information
    Islamorada, Florida Keys
    From
    $4,603
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    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Gym
    • Internet Access
    • Hot Tub
    • Refrigerator
    • Grill
    • Water Views
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Minimum Rental: 1 Month Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $7,671
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    4 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Internet Access
    • Balcony
    • Satellite TV
    • Patio
    • Hot Tub
    • Water Views
    • Grill
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) You'll love watching the fabulous sunsets over the tranquil waters in this semi-private lagoon setting. This is a three story single family home and offers two balconies overlooking the water and dock area. There's room to dock one 30' boat and a fish cleaning... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,650
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    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Shared Outdoor Pool...
    • Patio
    • Grill
    • Gym
    • Water Views
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Description….. MINIMUM STAY: Minimum Rental: 1 Month 5th Floor unit at one of Islamorada's favorite condo complexes. This unit was recently sold and the new owners are beginning to update some of the décor. You'll love the fantastic panoramic ocean views as you relax or dine on... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,929
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    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Patio
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Water Views
    • Grill
    • Shared Outdoor Pool...
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month 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 the Atlantic... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $16,738
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    5 of 5 stars (13) Excellent
    10 Bedrooms, 8 Bathrooms, Sleeps 20
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    Overview Reviews (13)
    Amenities & Details
    • Water Views
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Private Outdoor...
    • Waterfront
    • Ping Pong Table
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
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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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    Location Information
    Islamorada, Florida Keys 33036
    From
    $5,858
    / Month
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    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Shared Outdoor Pool...
    • Grill
    • Terrace
    • Refrigerator
    • Satellite TV
    • Balcony
    • Parking
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY 29 DAYS. BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL - For the guest who expects perfection this is it. This home was completely remodeled in 2013. There is 936 square feet of living area on the main level with 2 bedrooms, a full bath and an open living area. On the ground... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    From
    $5,565
    / Month
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    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Balcony
    • Parking
    • Refrigerator
    • Satellite TV
    • Grill
    • Terrace
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,790
    / Month
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Water Views
    • Hot Tub
    • Satellite TV
    • Grill
    • Shared Outdoor Pool...
    • Patio
    • Balcony
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Comfortably furnished and ready for you. 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, or watch the spectacular sunsets over the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,417
    / Week
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    1 / 19
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • Washer
    • Water Views
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This beautifully furnished and spacious... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $5,579
    / Week
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    5 Bedrooms, 5 Bathrooms, Sleeps 10
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • TV
    • Private Outdoor...
    • Waterfront
    • Water Views
    • Hot Tub
    • Ocean Views
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Islamorada Venetian Shores luxury waterfront 5BD/5BA with 100' dock and boat lift, custom pool with spa and waterfall, elevator & private master suite on the 3rd floor. Instant big boat access to both the ocean and bay from 100' wide, deep canal. Spacious home offers over 5,000 sf including porches... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,866
    / Month
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    1 / 29
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (8) Make Enquiry
    Overview Reviews (8)
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Stereo System
    • Satellite TV
    • Shared Outdoor Pool...
    • Dryer
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful three bedroom bay side townhouse with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $4,603
    / Week
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    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Microwave
    • Water Views
    • Air Conditioning
    • Dishwasher
    • Porch
    • TV
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This three bedroom, three bathroom condominium sits on a lushly landscaped property, offering the Florida Keys you've always imagined. Enjoy beautiful oceanfront vistas from one of two balconies. Take a dip in the spacious pool that sits right at the foot of the condo staircase. Or journey a few... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,929
    / Week
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    1 / 31
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Grill
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Washer
    • Water Views
    • Dryer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Affordable Venetian Shores canal home at the Mile Marker 86, Bay-side. Nice decor, recently updated with a private downstairs apartment. Two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs (with a complete kitchen and living room). Easy ocean or bay access via Snake Creek.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $4,882
    / Week
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    1 / 28
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (4) Make Enquiry
    Overview Reviews (4)
    Amenities & Details
    • Waterfront
    • Grill
    • Internet Access
    • Air Conditioning
    • Porch
    • Water Views
    • Stereo System
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    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
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    Location Information
    Islamorada, Florida Keys
    From
    $418
    / Night
    Payment Protection
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    3 Bedrooms, 5 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Watersports Nearby
    • Hot Tub
    • Air Conditioning
    • Water Views
    • Satellite TV
    • Ocean Views
    • Housekeeping...
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Luxurious end unit in Bay Harbour with a boat slip. Upon entering the unit you are greeted with the tranquil views of the harbor and ocean. Enjoy the ocean breeze from the large screen porch. Beautiful Bay Harbour gated condo community on lower Matecumbe, mm 74 1/2. Enjoy the sunrise or sunset... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $6,277
    / Month
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    4.5 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (4) Make Enquiry
    Overview Reviews (4)
    Amenities & Details
    • Waterfront
    • Water Views
    • Dishwasher
    • Microwave
    • Grill
    • TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A very charming and immaculate 3 bedroom home in Plantation Key. This home has excellent protected deep water dockage. Ocean views from balcony. Easy bay access via Tavernier Creek. Close to resturants and store. CLICK HERE to view photos on a mobile device. Additional amenities include:... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $8,369
    / Month
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    1 / 9
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Water Views
    • Stereo System
    • Waterfront
    • Boat Available
    • Washer
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A quaint bungalow on a not-so-quaint piece of oceanfront land right in the Heart of Islamorada! This home has two bedrooms, two bathrooms, and a lot of Keysy charm. During your stay, you will enjoy such amenities as a fishing dock with Chickee hut (1ft draft), cable television, a kayak, and a white... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,092
    / Week
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    1 / 36
    4 of 5 stars (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Reviews (16) Make Enquiry
    Overview Reviews (16)
    Amenities & Details
    • Satellite TV
    • Water Views
    • Waterfront
    • Stereo System
    • Wi-Fi
    • Air Conditioning
    • Boat Available
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,208
    / Week
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    1 / 30
    4.5 of 5 stars (7) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (7) Make Enquiry
    Overview Reviews (7)
    Amenities & Details
    • Internet Access
    • Dishwasher
    • Stereo System
    • Waterfront
    • TV
    • Grill
    • Water Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $5,579
    / Week
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    1 / 12
    Studio, 3 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Wi-Fi
    • Refrigerator
    • Washer
    • Waterfront
    • Dryer
    • Air Conditioning
    • TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This delightful 2 bedroom 2 bathroom with a detached 1 bedroom 1 bath downstairs is located on a quiet canal in Plantation Key at mile maker 90 ocean side. This home has a renovated kitchen and is beautifully decorated throughout. The property is fenced in and has amazing water views. You won't... View all property information
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    Location Information
    Islamorada, Florida Keys 33036