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Villas and Holiday Rentals in Islamorada, FL

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    From
    €3,995
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    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 / 13
    4 of 5 stars (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 of 5 stars (1) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 of 5 stars (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6
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    • DVD Player
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    About this property
    ****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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    €1,198
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Ocean Views
    • Waterfront
    • Air Conditioning
    • Shared Tennis Court
    • Private Fishing...
    • Hot Tub
    • Game Room
    • Wi-Fi
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
    About this property
    Welcome to your island paradise! Each time you open the door of this Islamorada vacation home the view of the ocean’s aquamarine color will take your breath away once again. Set just above the tops of softly swaying palm trees, views overlook the Atlantic Ocean, private boat dock, fish station,... View all property information
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    Islamorada, Florida Keys 33036
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    €4,438
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    1 / 8
    3 of 5 stars (1) Average
    3 Bedrooms, 4 Bathrooms, Sleeps 6
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    • Washer
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    • Pet-friendly
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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
    €123
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    1 Bedroom, 1 Bathroom, Sleeps 2
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    • Grill
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    • Stereo System
    • DVD Player
    • Wi-Fi
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    • TV
    • Refrigerator
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Enter through a private garden with a tropical atmosphere to a quiet and secluded room with a queen size bed and a private bath. The room is completely private and features a coffee maker, microwave, refrigerator, TV and free WiFi. Full breakfast.LOCATED IN A QUIET,SECLUDED , TROPICAL SETTING YET... View all property information
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    Islamorada, Florida Keys 33136
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    €159
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    1 Bedroom, 1 Bathroom, Sleeps 3
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    • Air Conditioning
    • Shared Outdoor Pool...
    • Watersports Nearby
    • Housekeeping...
    • DVD Player
    • Stereo System
    • Wi-Fi
    • TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
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    • ?
    About this property
    Malaysian room is poolside in a tropical atmosphere facing a beautiful waterfall. Features a mini kitchen with blender, coffee maker, microwave, refrigerator and toaster oven. A/C, heat, TV and WiFi. Includes a full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO... View all property information
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    Islamorada, Florida Keys 33036
    From
    €79
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    1 Bedroom, 1 Bathroom, Sleeps 2
    other travellers have booked this property
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    • DVD Player
    • Stereo System
    • Housekeeping...
    • Air Conditioning
    • Shared Outdoor Pool...
    • Watersports Nearby
    • Wi-Fi
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    A small stand alone room in the corner of the garden. Features a/c, coffee maker, free WiFi, grill on premises, heat, microwave, refrigerator, shared bathroom with one other couple, TV and includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO FISHING, DIVING,... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €4,438
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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
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    • Smoking allowed
    • Elder access
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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
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    From
    €7,945
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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
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    • x
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    • Elder access
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    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
    From
    €4,882
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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
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Elder access
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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
    €5,326
    / 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
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    • x
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    • Elder access
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    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
    €17,665
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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
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    • Smoking allowed
    • Elder access
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    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
    €1,953
    / Week
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    1 / 1
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
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    • TV
    • Balcony
    • Water Views
    • Dryer
    • Grill
    • Air Conditioning
    • Refrigerator
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Add some Caribbean spice to your next visit to the Florida Keys. This two-bedroom/two-and-half bath villa sits within Angler's Reef, a charming community of detached town homes that take their inspiration from the architecture of the British West Indies. Located at mile marker 85, on Windley Key,... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €2,219
    / Week
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    1 / 12
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Overview
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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
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    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
    €1,687
    / Month
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    1 / 15
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4
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    Overview Reviews (1)
    Amenities & Details
    • Shared Outdoor Pool...
    • Gym
    • Refrigerator
    • Water Views
    • Grill
    • Hot Tub
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. 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... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €4,660
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    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    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
    €2,219
    / Week
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    1 / 19
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview Reviews (1)
    Amenities & Details
    • Refrigerator
    • Water Views
    • Grill
    • Ceiling Fans
    • Satellite TV
    • Parking
    • 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: 7 Nights Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €2,841
    / Month
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Overview
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    • Water Views
    • Grill
    • Washer
    • Dryer
    • Satellite TV
    • Internet Access
    • Refrigerator
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    This charming 2 bedroom and 2 bathroom home is located at the 90 mile marker. This home is centrally located to shopping, restaurants, and grocery store. This home offers deep water dockage and easy access to the Atlantic Ocean via Tavernier Creek. Great outdoor space whether you are sitting on... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    From
    €2,219
    / Week
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    1 / 31
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
    €2,219
    / Week
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    1 / 27
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
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    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
    €2,042
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    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5
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    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
    €1,110
    / 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
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    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
    €1,775
    / Week
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    1 / 24
    4.5 of 5 stars (6) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (6) Make Enquiry
    Overview Reviews (6)
    Amenities & Details
    • Internet Access
    • TV
    • Porch
    • Stereo System
    • Dishwasher
    • Waterfront
    • Grill
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. VACATION RENTAL LICENSE: VR-039 CLICK HERE to view photos on a mobile device.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €3,551
    / Month
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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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    Location Information
    Islamorada, Florida Keys 33036
    From
    €5,770
    / Month
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    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (1) Make Enquiry
    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
    €1,864
    / Month
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    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    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
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    • 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
    €3,906
    / Month
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    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Overview
    Amenities & Details
    • Patio
    • Hot Tub
    • Grill
    • Internet Access
    • Water Views
    • Shared Outdoor Pool...
    • Gym
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Islamorada, Florida Keys 33036
    From
    €2,929
    / Week
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    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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
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    • Smoking allowed
    • Elder access
    • x
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    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
    €2,841
    / Month
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    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • 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
    • ?
    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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    Location Information
    Islamorada, Florida Keys 33036
    From
    €3,373
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    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • 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
    €3,551
    / Month
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    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • 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
    €2,574
    / Month
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    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • 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
    €3,995
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    1 / 34
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Private Outdoor...
    • Water Views
    • Washer
    • Air Conditioning
    • Patio
    • Dryer
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    How about sipping coffee and watching the sun come up as you fish off the end of your very own 300 foot pier? Sounds good, right? Well, that's just one reason to stage your upcoming vacation at this lovely, hacienda-style home on a quaint and private oceanfront street in Islamorada. CLICK HERE to... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €1,864
    / Month
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    1 / 18
    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
    €2,042
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • 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
    €2,929
    / Month
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    1 / 20
    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
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    €4,882
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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
    • ?
    • 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
    €1,332
    / 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
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    • 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
    €1,687
    / Month
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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
    €3,728
    / 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
    €3,542
    / 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
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    • 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
    €1,775
    / 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
    €2,663
    / Month
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    1 / 16
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Water Views
    • Dryer
    • Washer
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    'Cute & Keysy' perfectly describe this Conch home! Located in the Tollgate Shores subdivision of Lower Matecumbe (south Islamorada), this delightfully quaint home has lots of character, charm, and is well-maintained. You'll enjoy sea breezes and the smell of salty air coming through the windows of... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €2,175
    / 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
    • ?
    • ?
    • 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
    €2,858
    / Month
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    1 / 29
    4.5 of 5 stars (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    Amenities & Details
    • Washer
    • Dryer
    • Wi-Fi
    • Stereo System
    • Shared Outdoor Pool...
    • Satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Come and relax at our beautiful, newly renovated town home 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 tennis courts, a swimming pool, a clubhouse, a private beach and a... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €2,042
    / 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
    €4,705
    / Week
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    1 / 50
    4 of 5 stars (17) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Reviews (17) Make Enquiry
    Overview Reviews (17)
    Amenities & Details
    • Garage
    • Dishwasher
    • Grill
    • Water Views
    • Air Conditioning
    • Waterfront
    • TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This oceanfront home will surely get you in a Keys state of mind. Featuring five bedrooms, a pool, and an expansive private beach, its ideal for anything from a reunion of extended family or friends, to a small wedding, to a relaxing family vacation. The 4,300 square foot house will capture your... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    €3,995
    / Month
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    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • TV
    • Washer
    • Deck
    • Air Conditioning
    • Water Views
    • Private Outdoor...
    • Waterfront
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Great 2 bedroom 2 bath with a detached one bedroom apartment downstairs located in Plantation Key at mm 90. This home does have a private pool and is fenced in. Very comfortable home for your get-away. Stay for a month or multiple months. Close to restaurants and our grocery store. Please... View all property information
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    Location Information
    Islamorada, Florida Keys 33036