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Holiday Rentals in Islamorada, FL

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    From
    $4,188
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    1 / 16
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 / 31
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4.5 of 5 stars (4) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Waterfront
    • Water Views
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    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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    Islamorada, Florida Keys 33036
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    1 / 38
    4 Bedrooms, 3 Bathrooms, Sleeps 10
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    • Air Conditioning
    • Waterfront
    • DVD Player
    • Hot Tub
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    About this property
    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully... View all property information
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    Islamorada, Florida Keys 33036
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    1 / 9
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Air Conditioning
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    • Boat Available
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    • Pet-friendly
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    • x
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    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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    Islamorada, Florida Keys 33036
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    4 of 5 stars (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Satellite TV
    • Water Views
    • Waterfront
    • Stereo System
    • Wi-Fi
    • Air Conditioning
    • Boat Available
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
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    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
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    $205
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    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
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    • Internet Access
    • Washer
    • DVD Player
    • Stereo System
    • Deck
    • Satellite TV
    • Air Conditioning
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Elder access
    • x
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    About this property
    MINIMUM STAY 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 spacious... View all property information
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    Location Information
    Islamorada, Florida Keys
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    $163
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    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 12
    Overview Make Enquiry
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    • Washer
    • Air Conditioning
    • Deck
    • Internet Access
    • Stereo System
    • Satellite TV
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY 1 MONTH: Enjoy your stay in this gorgeous single family home. You’ll love the convenient location in the Ocean Shores area of Key Largo. There’s easy ocean access from this 90' concrete dock. Water, electricity, fish cleaning station and gas barbecue grill are all handy. Not... View all property information
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    Location Information
    Islamorada, Florida Keys
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    $3,211
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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
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    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
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    From
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    1 / 34
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Enquiry
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    • Private Outdoor...
    • Water Views
    • Washer
    • Air Conditioning
    • Patio
    • Dryer
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
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    • x
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    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
    $2,094
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    1 / 13
    4.5 of 5 stars (16) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (16) Make Enquiry
    Overview Reviews (16)
    Amenities & Details
    • TV
    • Waterfront
    • Water Views
    • Air Conditioning
    • Patio
    • Grill
    • Deck
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Please send us an inquiry or call us for availability. We have a couple of units. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool, sandy beachy area, and fishing pier with flats boat dockage (drawing 24' or less) located directly on the ocean.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $7,399
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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
    $4,188
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    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
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    • Washer
    • TV
    • Air Conditioning
    • Dryer
    • Water Views
    • Waterfront
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    This delightful 2 bedroom, 2 bathroom home is located in Port Antigua (south Islamorada) at the 74 mile marker. While not located directly on the bay, you'll still be able enjoy the homeowners park that has a beach and beautiful sunsets. The home comes equipped with Wi-Fi internet. Click here to... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,792
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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
    $7,329
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    1 / 35
    4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Overview
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    • Water Views
    • Stereo System
    • Satellite TV
    • Boat Available
    • Grill
    • Dishwasher
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $1,396
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    1 / 10
    4.5 of 5 stars (3) Very good
    2 Bedrooms, Sleeps 4
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    Amenities & Details
    • Waterfront
    • Shared Tennis Court
    • Air Conditioning
    • Internet Access
    • Sauna
    • TV
    • Water Views
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Please send us an inquiry or call us for availability. Prices vary on the units. Sea Gulls Condominiums, on the shores of the Atlantic Ocean provides vacationers the splendor of the Atlantic waters with luxury living at an affordable price. This perfect family vacation destination offers something... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $4,467
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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
    • ?
    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
    From
    $4,188
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    1 / 30
    4.5 of 5 stars (8) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10
    Overview Reviews (8) Make Enquiry
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Stereo System
    • Water Views
    • TV
    • Dishwasher
    • Waterfront
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Amazing ocean views can be enjoyed from this beautiful stilt home with seperate mother-in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $6,282
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    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
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    • TV
    • Washer
    • Deck
    • Air Conditioning
    • Water Views
    • Private Outdoor...
    • Waterfront
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    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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    Islamorada, Florida Keys 33036
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    $3,490
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    1 / 29
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (4) Make Enquiry
    Overview Reviews (4)
    Amenities & Details
    • Dryer
    • Wi-Fi
    • DVD Player
    • Washer
    • TV
    • Water Views
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees. Large sandy beach and great dock. Interior photos available! Mile Marker 76, Bayside. Home has 2 bedrooms & 2 bathrooms upstairs, and a separate 2 bedroom, 2... View all property information
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    Location Information
    Islamorada, Florida Keys
    From
    $8,900
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    1 / 12
    5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Overview
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    • Dishwasher
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • Grill
    • Internet Access
    • Water Views
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people. The Upper Duplex &... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    $2,303
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    1 / 5
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Waterfront
    • Satellite TV
    • Hot Tub
    • Porch
    • Internet Access
    • Dishwasher
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Plantation Key canal home. Nice new home with screened porch and pool table! Delightfully furnished for a comfortable stay. Excellent outdoor entertaining space, great for soaking in the hot tub, gazing at fish in the canal, having cocktails under the Chickee, or for the kids to run around and... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    $1,850
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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, Sleeps 4
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
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    • Water Views
    • TV
    • Dryer
    • Waterfront
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Please send us an inquiry or call us for availability. We have condos and townhomes. Prices vary on the units. Your own tropical paradise overlooking the fabulous Florida Bay in Islamorada. Futura Yacht Club is a 70 unit community with a 53 slip marina and accommodations available for that... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,211
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    1 / 27
    4 of 5 stars (6) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Reviews (6) Make Enquiry
    Overview Reviews (6)
    Amenities & Details
    • Water Views
    • Dryer
    • Stereo System
    • Satellite TV
    • Washer
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Modern canal home with views of Snake Creek. The property is completely fenced in. Third level master suite with private master balcony. Well furnished with all the extras. Easy ocean or bay access and dockage up to 50 feet. Open floor plan with regulation pool table and screened in porch. This... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $130
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    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview
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    • Dryer
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Deck
    • Patio
    • Air Conditioning
    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
    Vacation in beautiful peaceful Islamorada, in the Florida Keys. Islamorada, 'Fishing Capital of the World'. Bayside access Townhouse is a newly redone 2 bedroom, loft, 1 1/2 bath, comfortably sleeps 6 adults, patio with BBQ. Fully furnished and kitchen totally equipped. Washer/Dryer, Flat screen... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $652
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    1 / 19
    6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Overview
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    • Internet Access
    • Deck
    • Balcony
    • Private Outdoor...
    • Waterfront
    • Air Conditioning
    • Patio
    • Fireplace
    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
    This is a 6 bedroom pool home with direct dockage just off Snake Creek. Home has 2 kings, 3 queens, and 2 twins. Located at mile marker 86 on the bay side Beds: 2 King Beds, 2 Queen Beds, 1 Double Bed, 2 Twin Beds View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $758
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    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
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    • Internet Access
    • Satellite TV
    • Deck
    • Waterfront
    • Stereo System
    • Dryer
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Ocean front retreat with overwhelming views of the Atlantic, large open verandahs, 100 feet of very private white sandy beach, and a gated entrance. The beach is very private on 3/4 of an acre loaded with palm trees. You can snorkel in the backyard on coral reefs within 1000 feet of the shore. Use... View all property information
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    Location Information
    Islamorada, Florida Keys
    From
    $6,980
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    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Overview
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    • Refrigerator
    • Washer
    • Air Conditioning
    • Internet Access
    • Patio
    • Dryer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Spacious 3/3 canal front home in Lower Matecumbe. 75 Ft of dock with 45 FT cut-in for extra boat protection. Walk down the street to world famous Robbies for dinner/drinks and boat, kayak and jet-ski rentals. Located on MM 77, this place is close to many restaurant and tourist sites. Just a few... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $4,188
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    1 / 35
    5 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Water Views
    • Microwave
    • Dishwasher
    • Waterfront
    • TV
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Prestigious Venetian Shores subdivision in Islamorada! This vacation home has 5 bedrooms and 3 bathrooms with 100 concrete dock. The house is situated into two separate living quarters. Upstairs is a large master suite and 2 guest bedrooms, cathedral ceilings & fully stocked, eat-in kitchen,... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $454
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    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Private Outdoor...
    • Boat Available
    • Waterfront
    • Stereo System
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $498
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    1 / 24
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Private Outdoor...
    • Stereo System
    • Waterfront
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Your Florida Keys Getaway The Florida Keys are like no other place on earth offering Your customized 'Florida Keys Getaway' located in Venetian Shores mile marker 86 bay side Islamorada's premier boating neighborhood situated just four lots from Snake Creek, a waterway between island's that... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $599
    / Night
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    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Private Outdoor...
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Stereo System
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Oceanfront splendor on the Atlantic ocean. Has a 350' pier that can accomodate most any size boat. Just relax by the pool on those hot days or take a dip in the ocean. The pool is heated for the winter months. The house is extremely private. There is a wooden fence around the house and... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    From
    $209
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    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Refrigerator
    • Satellite TV
    • Washer
    • Dryer
    • Air Conditioning
    • DVD Player
    • Private Outdoor...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $4,188
    / Month
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    1 / 18
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Refrigerator
    • TV
    • Shared Outdoor Pool...
    • Air Conditioning
    • Parking
    • Linens Provided
    • Water Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Summer Seas is located directly on the Florida Bay is the perfect sunny getaway! The complex is centrally located at mm 88. There is also on-site community laundry, a pool, hot tub, and clubhouse. Islamorada, the 'Village of Islands,' is widely known as the sportfishing capital of the world. Its... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $140
    / Night
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    1 / 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Stereo System
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Call Property Manager for Best Rate. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool sandy Beachfront, fishing pier with flats boat dockage (drawing 24' or less) located directly on the ocean your views could NOT be any better. Under the condo... View all property information
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    Location Information
    Islamorada, Florida Keys
    From
    $209
    / Night
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    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Deck
    • Boat Available
    • Air Conditioning
    • Water Views
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Newly remodeled mobile home cottage is more than you've imagined so far. Enjoy the bright open living area with panoramic horizon view from the kitchen/living room. Open the 2 sets of French Doors to bring the outside, in. Sit on the wrap around deck to watch the Sun Rise out of the water, year... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $140
    / Night
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    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Washer
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • Internet Access
    • DVD Player
    • Deck
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM RENTAL 1 MONTH: 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 share... View all property information
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    Location Information
    Islamorada, Florida Keys
    From
    $4,188
    / Month
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    1 / 23
    3.5 of 5 stars (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Dryer
    • Wi-Fi
    • Water Views
    • Satellite TV
    • Washer
    • Stereo System
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This 2Bed/2Bath stilt home is located at mile marker 89 at the very end of Indian Waterways subdivision. Located on a canal with approximately 30' of dockage, you'll have almost immediate access to the Florida Bay and just a 7 minute boat ride to Tavernier Creek, which takes right over to the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $149
    / Night
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    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Washer
    • Stereo System
    • Internet Access
    • Air Conditioning
    • Deck
    • DVD Player
    • Satellite TV
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY 1 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
    From
    $4,188
    / Month
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    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Washer
    • Dryer
    • Waterfront
    • Water Views
    • Shared Tennis Court
    • Air Conditioning
    • Internet Access
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Please send us an inquiry or call us for availability. Prices vary on the units. 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
    $135
    / Night
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    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Washer
    • DVD Player
    • Satellite TV
    • Deck
    • Internet Access
    • Stereo System
    • Air Conditioning
    • Dryer
    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
    From
    $88
    / Night
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    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • Washer
    • Deck
    • Internet Access
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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 the balcony. There's plenty of comfortable... View all property information
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    Location Information
    Islamorada, Florida Keys
    From
    $233
    / Night
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    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Washer
    • Deck
    • Internet Access
    • Stereo System
    • Satellite TV
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY 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
    From
    $244
    / Night
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    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Deck
    • Satellite TV
    • Air Conditioning
    • Dryer
    • Washer
    • Stereo System
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • 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 home. It is... View all property information
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    Location Information
    Islamorada, Florida Keys
    From
    $195
    / Night
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    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    • Deck
    • Dryer
    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
    From
    $107
    / Night
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    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Stereo System
    • Satellite TV
    • DVD Player
    • Water Views
    • Air Conditioning
    • Internet Access
    • Deck
    • Washer
    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. Watch the... View all property information
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    Location Information
    Islamorada, Florida Keys
    From
    $498
    / Night
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Stereo System
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ower 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 sleeps up to 6 people - rent one or all... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $1,124
    / Week
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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
    Beautiful three bedroom townhouse on the Bay side with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful, newly renovated townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $529
    / Night
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    1 / 14
    1 Bedroom, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • DVD Player
    • Deck
    • Satellite TV
    • Washer
    • Dryer
    • Internet Access
    • Stereo System
    • Air Conditioning
    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 restaurants.... View all property information
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    Location Information
    Islamorada, Florida Keys