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House Rentals and Vacation Home Rentals in Florida Keys, FL

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    $6,500
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    1 / 32
    Tavernier
    4 Bedrooms, 3 Bathrooms, Sleeps 10
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    From
    $427
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    1 / 29
    5 of 5 stars (3) Excellent
    Marathon
    2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 / 12
    5 of 5 stars (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    $385
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    1 / 29
    4 of 5 stars (12) Very good
    Marathon
    4 Bedrooms, 2 Bathrooms, Sleeps 10
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    • Air Conditioning
    • Water Views
    • DVD Player
    • Boat Available
    • Private Outdoor...
    • Satellite TV
    • Waterfront
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This 4 bedroom, 2 bath property is great for family vacations. Less than 30% of all rentals in Marathon are 4 bedroom or larger. HOW MANY PEOPLE CAN SLEEP AT THIS 4 BEDROOM? Our rental license allows up to 10 people to stay overnight. Two of the... View all property information
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    Marathon, Florida Keys 33050
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    $300
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    1 / 32
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Stereo System
    • Internet Access
    • Water Views
    • Private Outdoor...
    • DVD Player
    • Waterfront
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it’s own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony. The... View all property information
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    Marathon, Florida Keys 33050
    From
    $400
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    1 / 11
    4 of 5 stars (1) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Water Views
    • Hot Tub
    • Grill
    • Washer
    • Internet Access
    • Balcony
    • Dishwasher
    • Stove
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a beautiful top floor two bedroom ocean-view unit at 1800 Atlantic. It is an extra large floor plan with expansive views You cannot get a better view than this. There is a full size fully equipped eat in Kitchen. Full size washer & dryer. Both bathrooms were renovated in 2013. The... View all property information
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    Key West, Florida Keys 33040
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    $570
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    1 / 44
    4.5 of 5 stars (11) Very good
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    other traveler has booked this property
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Boat Available
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This vacation rental puts you on your own private tropical island in the Gulf of Mexico named Pretty Joe Rock. You have your own 17 foot boat for the entire week! ARE WE THE ONLY PEOPLE ON THE ISLAND? Your family or group will be the only people on Pretty... View all property information
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    Location Information
    Marathon, Florida Keys 33050
    From
    $350
    / Night
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    1 / 10
    5 of 5 stars (3) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (3) Make Inquiry
    Overview Reviews (3)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Unit C232 is one of the premium rental Condo's in the 1800 Atlantic Complex. Beautifully decorated with higher end furnishings. Top of the line full size fully equipped eat in Kitchen. Dining room area and spacious living room. Both Bedrooms and the living room open onto the expansive private... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $210
    / Night
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    1 / 12
    4.5 of 5 stars (12) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    • Wireless Internet • Full Kitchen Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs tiled... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $4,000
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    1 / 12
    Islamorada
    Studio, 3 Bathrooms, Sleeps 4
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    • Wi-Fi
    • Refrigerator
    • Washer
    • Waterfront
    • Dryer
    • Air Conditioning
    • TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This delightful 2 bedroom 2 bathroom with a detached 1 bedroom 1 bath downstairs is located on a quiet canal in Plantation Key at mile maker 90 ocean side. This home has a renovated kitchen and is beautifully decorated throughout. The property is fenced in and has amazing water views. You won't... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    From
    $4,000
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    1 / 14
    5 of 5 stars (8) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (8) Make Inquiry
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    Amenities & Details
    • Washer
    • Private Outdoor...
    • Patio
    • Grill
    • Air Conditioning
    • Wi-Fi
    • TV
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    THIS PROPERTY IS A MONTHLY ONLY RENTAL Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining, you are steps away from... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $325
    / Night
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    1 / 25
    5 of 5 stars (4) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (4) Make Inquiry
    Overview Reviews (4)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Great 3rd floor 2 bedroom 2 bath rental unit at 1800 Atlantic. All furnishings replaced in 2011,decorated in an elegant contemporary style. This unit is spacious with a full size fully equipped eat in Kitchen. There is a king bed in the master bedroom, 2 twin beds in the 2nd bedroom and a queen... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $350
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    1 / 8
    5 of 5 stars (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    2 bedroom 2 bath top floor ocean-view condo at 1800 Atlantic. This unit has been totally renovated and no attention to detail spared. The Master Bedroom has king bed, The guest bedroom has a queen and the living room has a queen pull-out sleeper sofa. High speed interent available. There is a full... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $300
    / Night
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    1 / 11
    3 of 5 stars (4) Average
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview Reviews (4)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Fabulous spacious two bedroom condominiums, directly on the Atlantic Ocean in Key West Florida. The Condo is fully equipped with a full size Kitchen. There is also a full size washer & dryer for your convenience. All rooms have a color cable TV and the unit has high Unit has an extensive private... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $3,500
    / Week
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    1 / 28
    5 of 5 stars (4) Excellent
    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (4) Make Inquiry
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    Amenities & Details
    • Waterfront
    • Grill
    • Internet Access
    • Air Conditioning
    • Porch
    • Water Views
    • Stereo System
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This home is located in a nice, quiet family neighborhood at the 90 mile marker (90 miles from Key West), Bayside. The house sits on the last canal of the neighborhood...very short boat ride to the bay (only a minute or so). Deep water dockage - 65' of dock space. There is an downstairs fully... View all property information
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    Location Information
    Islamorada, Florida Keys
    From
    $427
    / Night
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    1 / 28
    4.5 of 5 stars (4) Very good
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (4) Make Inquiry
    Overview Reviews (4)
    Amenities & Details
    • Deck
    • Grill
    • Water Views
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This vacation rental puts you on your own tropical island in a quiet cove of protected mangroves in the Gulf of Mexico. You stay on a 2 bedroom houseboat that is docked on the island. You have your own 17 foot boat for the entire week! HOW MANY PEOPLE CAN... View all property information
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    Location Information
    Marathon, Florida Keys 33050
    From
    $182
    / Night
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    1 / 22
    2.5 of 5 stars (3) Poor
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (3) Make Inquiry
    Overview Reviews (3)
    Amenities & Details
    • Internet Access
    • Boat Available
    • Waterfront
    • Satellite TV
    • Water Views
    • DVD Player
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? Palm Place is the perfect vacation home for thrifty, active, travelers on the go! The home is centrally located on Overseas Highway in the town of Marathon. HOW MANY PEOPLE CAN SLEEP AT PALM PLACE? Our rental license allows up to 6 people to stay... View all property information
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    Location Information
    Marathon, Florida Keys 33050
    From
    $413
    / Night
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    1 / 27
    4.5 of 5 stars (5) Very good
    Marathon
    4 Bedrooms, 4 Bathrooms, Sleeps 10
    Overview Reviews (5) Make Inquiry
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    Amenities & Details
    • Private Outdoor...
    • Water Views
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This 4 bedroom, 4 bath property is great for family vacations. Less than 30% of all rentals in Marathon are 4 bedroom or larger. HOW MANY PEOPLE CAN SLEEP AT THIS 4 BEDROOM? Our rental license allows up to 10 people to stay overnight. Three of the... View all property information
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    Location Information
    Marathon, Florida Keys 33050
    From
    $1,184
    / Night
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    1 / 31
    5 of 5 stars (2) Excellent
    Marathon
    12 Bedrooms, 8 Bathrooms, Sleeps 30
    Overview Reviews (2) Make Inquiry
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    Amenities & Details
    • Private Outdoor...
    • Water Views
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Waterfront
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This rental offers a great option for multi-family vacationing by providing three 4-bedroom homes side-by-side. This gives you 3 kitchens, 3 pools, 3 deep water docks, 3 gas grills, parking for 8 vehicles and 6 kayaks! These properties are non-smoking and... View all property information
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    Location Information
    Marathon, Florida Keys 33050
    From
    $3,000
    / Month
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    1 / 15
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 2
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    • TV
    • Wi-Fi
    • Dryer
    • Refrigerator
    • Air Conditioning
    • Washer
    • Stove
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Can you say “perfectly adorable”? We thought so. Now picture “perfectly adorable” and you have found Poppy. Poppy is a one-bedroom, one-bath home that is perfect for one or a couple. From the moment you step up onto the front porch, which is perfect for people watching, and into the open... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    From
    $798
    / Night
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    1 / 42
    5 of 5 stars (1) Excellent
    Marathon
    8 Bedrooms, 6 Bathrooms, Sleeps 20
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    Amenities & Details
    • Private Outdoor...
    • Satellite TV
    • Boat Available
    • Internet Access
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This rental offers a great option for multi-family vacationing by providing two 4-bedroom homes side-by-side. This gives you 2 kitchens, 2 pools, 2 deep water docks, 2 gas grills, parking for 5 vehicles and 6 kayaks! These properties are non-smoking and... View all property information
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    Location Information
    Marathon, Florida Keys 33050
    From
    $343
    / Night
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    1 / 34
    5 of 5 stars (1) Excellent
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Waterfront
    • Internet Access
    • Water Views
    • Deck
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to our Keys vacation home! We have a lovely home on a large fenced lot in a very private, quiet neighborhood. This Coco Plum location is one of the best in the heart of the Florida Keys National Marine Sanctuary. Located on a very wide, sailboat deep-water canal. Our 110' wide fenced lot... View all property information
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    Location Information
    Marathon, Florida Keys 33050
    From
    $11,400
    / Month
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    1 / 34
    5 of 5 stars (3) Excellent
    Matecumbe Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Reviews (3) Make Inquiry
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    Amenities & Details
    • Internet Access
    • Boat Available
    • Microwave
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Exceptional oceanfront home equipped with a sandy beach and forever views! Exquisite design and rich appointments compliment this oceanfront home in Lower Matecumbe, (mile marker 75, South Islamorada). You will enjoy private terraces from each bedroom overlooking picturesque sunrises and panoramic... View all property information
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    Location Information
    Matecumbe Key, Florida Keys 33036
    From
    $2,450
    / Week
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    1 / 19
    5 of 5 stars (3) Excellent
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    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
    $3,000
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    1 / 16
    Islamorada
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
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    • Water Views
    • Dryer
    • Washer
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • 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
    $6,500
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    1 / 34
    4 of 5 stars (1) Very good
    Key Largo
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Internet Access
    • Stereo System
    • Washer
    • Air Conditioning
    • Dryer
    • Waterfront
    • TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in Key Largo at mile marker 95, oceanside, this pool home will really seal the deal. Just remodeled, and offering stunning Atlantic views, the home is ideal for a family seeking a combination of camaraderie and privacy. Divided into separate units on its two floors, each with its own... View all property information
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    Location Information
    Key Largo, Florida Keys 33037
    From
    $357
    / Night
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    1 / 28
    5 of 5 stars (15) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5
    Overview Reviews (15) Make Inquiry
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    Amenities & Details
    • Washer
    • TV
    • Patio
    • Private Outdoor...
    • Dryer
    • Wi-Fi
    • Air Conditioning
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Debating between the comfort of a chic hotel and the thrill of more authentic accommodations? You will get the best of both worlds with this cozy 2 bedroom home, currently available for up to 5 guests (please see our calendar). Potter’s Cottage is located in the heart of Old Town – Key West’s... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $2,000
    / Night
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    1 / 5
    4 of 5 stars (1) Very good
    Big Pine Key
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Reviews (1) Make Inquiry
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    Amenities & Details
    • Washer
    • DVD Player
    • Grill
    • Dryer
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy a quite setting on this canal front lot. With its wooded and open area you can enjoy cooking on the charcoal grill. The Home provides a quite place to rest in between shopping, swimming, and dining at restaurants in the near by towns and other key islands. Park your boat in the canal while... View all property information
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    Location Information
    Big Pine Key, Florida Keys 33043
    From
    $3,000
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    1 / 24
    5 of 5 stars (2) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Reviews (2) Make Inquiry
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Waterfront
    • Porch
    • Air Conditioning
    • Dishwasher
    • Boat Available
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Q: What's better than vacationing in the Florida Keys? A: Vacationing in a charmingly cute canal-front home in the Florida Keys! And this home takes the cake for cute! Located at mile marker 101 on the bay-side in Key Largo, this home is equipped to make your month (or longer!) in the Keys one to... View all property information
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    Location Information
    Key Largo, Florida Keys 33070
    From
    $2,550
    / Month
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    1 / 11
    Ramrod Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Inquiry
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    • Internet Access
    • Linens Provided
    • DVD Player
    • Microwave
    • TV
    • Porch
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • x
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    About this property
    This Ramrod Key rental is a great spot for your next Florida Keys vacation. Comfortable and affordable, with 2 bedrooms and 2 bathrooms. The ample size kitchen and living area and the screened porch overlooks a peaceful canal with 52 feet of dock space for your boat. Ramrod Key, located at mile... View all property information
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    Location Information
    Ramrod Key, Florida Keys
    From
    $795
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    1 / 37
    5 of 5 stars (11) Excellent
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Grill
    • Wi-Fi
    • Dryer
    • TV
    • Air Conditioning
    • Washer
    • Private Outdoor...
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • x
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    • Elder access
    • x
    • ?
    About this property
    Just a half block off Duval you'll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you'll find yourself in the private brick courtyard facing the home with its French doors and... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $3,800
    / Month
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    1 / 17
    5 of 5 stars (1) Excellent
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    Overview Reviews (1)
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    • Stereo System
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Washer
    • Deck
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Please contact us for current pricing details and availability - we do not maintain calendars OVERVIEW The Turtle House is a 100+ year old recently completely renovated Conch house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $300
    / Night
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    1 / 40
    5 of 5 stars (6) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    other travelers have booked this property
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    Amenities & Details
    • Refrigerator
    • Terrace
    • Central Heating
    • Balcony
    • Gym
    • Parking
    • Linens Provided
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    * This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it’s own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony.... View all property information
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    Location Information
    Marathon, Florida Keys 33050
    From
    $275
    / Night
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    1 / 24
    4.5 of 5 stars (3) Very good
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Reviews (3) Make Inquiry
    Overview Reviews (3)
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Internet Access
    • Waterfront
    • Patio
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Why rent a hotel in Key Largo when you can stay on board our FABULOUS houseboat rental Calypso. Docked in the heart of Key Largo, your stay on board our boat will be so surreal you won't believe it's a reality! This luxury home on the water, is a boat lovers dream. With 3 bedrooms and a sleeper... View all property information
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    Location Information
    Key Largo, Florida Keys 33037
    From
    $5,000
    / Week
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    1 / 38
    Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Private Outdoor...
    • TV
    • Wi-Fi
    • Water Views
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,800
    / Month
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    1 / 14
    5 of 5 stars (4) Excellent
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 5
    Overview Reviews (4) Make Inquiry
    Overview Reviews (4)
    Amenities & Details
    • Hot Tub
    • Deck
    • Internet Access
    • Air Conditioning
    • Washer
    • Dryer
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Please contact us for current pricing details and availability - we do not maintain calendars OVERVIEW The Conch House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of five (5)... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $1,400
    / Week
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    1 / 29
    4.5 of 5 stars (2) Very good
    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (2) Make Inquiry
    Overview Reviews (2)
    Amenities & Details
    • Wi-Fi
    • Water Views
    • DVD Player
    • Satellite TV
    • Dryer
    • Washer
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to our slice of paradise! Come and relax at our beautiful 3-bedroom home in the Florida Keys. Our home is located in Tavernier, the Sport Fishing Capital of the World. It is a private, gated home directly on the water with a small pier & fishing/boat dock. Our two-story home has master... View all property information
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    Location Information
    Tavernier, Key Largo 33070
    From
    $5,000
    / Month
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    1 / 16
    5 of 5 stars (1) Excellent
    Long Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview Reviews (1)
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    • Washer
    • Grill
    • TV
    • Dryer
    • Private Outdoor...
    • Wi-Fi
    • Waterfront
    • 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
    Cozy, canalfront pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Bay access and a short ride to the Atlantic Ocean. The bed rooms are located in a separated, quiet part of the house, while the living, dining, and kitchen are open for enjoying each... View all property information
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    Location Information
    Long Key, Florida Keys 33036
    From
    $1,000
    / Night
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    1 / 72
    4 of 5 stars (6) Very good
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview Reviews (6)
    Amenities & Details
    • Boat Available
    • Private Outdoor...
    • Water Views
    • Satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
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    About this property
    In the Florida Keys At MM 50 - East Sister Rock Island is a ¼ mile off the Atlantic shore of Marathon. On this private island sits a dream come true getaway home with 5000+ square feet of living area including a 2700 square foot veranda, boat dock (fisherman's dream), helicopter launch pad and many... View all property information
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    Location Information
    Marathon, Florida Keys 33050
    From
    $6,000
    / Month
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    1 / 9
    5 of 5 stars (2) Excellent
    Islamorada
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Air Conditioning
    • Water Views
    • Stereo System
    • Waterfront
    • Boat Available
    • Washer
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • 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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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,220
    / Month
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    1 / 29
    4.5 of 5 stars (3) Very good
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Overview Reviews (3)
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    • 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
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    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
    $170
    / Night
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    1 / 38
    4.5 of 5 stars (4) Very good
    Key Largo
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Overview Reviews (4)
    Amenities & Details
    • Satellite TV
    • Water Views
    • Washer
    • Deck
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Mile Marker 106 Please check calendar before you send you request:) Time for a getaway? Book today!! Need a family getaway, a group retreat, a quick escape just an hour from Miami International airport? Look no further! Wedding party need a place to stay??? Mini Lobster season, Memorial Day,... View all property information
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    Location Information
    Key Largo, Florida Keys 33037
    From
    $145
    / Night
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    1 / 29
    3.5 of 5 stars (13) Average
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenities & Details
    • Hot Tub
    • Water Views
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Ocean Pointe Suites in Key Largo is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private gatehouse and road. You have the choice of a one bedroom or two bedroom suite with either Island or... View all property information
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    Location Information
    Tavernier, Key Largo 33070
    From
    $200
    / Night
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    1 / 23
    1 of 5 stars (1) Terrible
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 6
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • TV
    • Internet Access
    • Balcony
    • Microwave
    • Air Conditioning
    • Water Views
    • Terrace
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Have you ever wondered what it would be like to live on a boat? Well now you can try out the liveaboard experience on board Capt Andy, a 43 ft fishing boat in Key West! This is the perfect rental for a group of boat loving friends looking for a budget friendly rental in Key West. Featuring a full... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $1,500
    / Week
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    1 / 36
    4 of 5 stars (16) Very good
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Amenities & Details
    • Satellite TV
    • Water Views
    • Waterfront
    • Stereo System
    • Wi-Fi
    • Air Conditioning
    • Boat Available
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $1,235
    / Week
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    1 / 29
    4.5 of 5 stars (24) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    Overview Reviews (24)
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    • Grill
    • Internet Access
    • DVD Player
    • TV
    • Hairdryer
    • Shared Outdoor Pool...
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Smoking allowed
    • Elder access
    • ?
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    About this property
    LAVENDER JUNGLE: 2 bedroom 1 bath downstairs Shipyard condo located in Truman Annex. Renovated kitchen and upgraded bathroom. Large brick patio and grill. Master bedroom with queen bed and guest bedroom with 2 twins on either side of the full bathroom. Well-equipped kitchen. Truman Annex is a... View all property information
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    Location Information
    Key West, Florida Keys 33040
    From
    $4,500
    / Month
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    1 / 20
    4.5 of 5 stars (4) Very good
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Overview Reviews (4)
    Amenities & Details
    • Waterfront
    • Water Views
    • Dishwasher
    • Microwave
    • Grill
    • TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Smoking allowed
    • Elder access
    • x
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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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    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,300
    / Week
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    1 / 30
    4.5 of 5 stars (7) Very good
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
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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
    From
    $2,000
    / Week
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    1 / 24
    4.5 of 5 stars (6) Very good
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
    $2,500
    / Month
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    1 / 23
    3 of 5 stars (1) Average
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 2
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
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    • Washer
    • Refrigerator
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Dryer
    • Patio
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    SUMMER SPECIAL TAKE 10% OFF AUGUST AND SEPTEMBER! Gorgeous studio apartment on the first floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street. You will be living the Key West Life to... View all property information
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    Location Information
    Key West, Florida Keys 3300