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Matecumbe Key Vacation Rentals

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    Travelers to Matecumbe Key are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    All 16 Rentals in Matecumbe Key
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    75731 Overseas Highway1 / 32
    (13)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    75130 Overseas Highway1 / 19
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE1 / 16
    (9)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Private Beachfront Paradise1 / 45
    (12)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Sauna
    • Waterfront
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 14, 2016
    The friends we haven't seen in over 25-years since high school, decided to reunite in Islamorada, FL. The moment we set foot on this property, we knew we were in for a great...
    Reviewed August 24, 2016
    We just got back from a week in this beautiful house. We traveled with extended family and 2 young children- everyone loved it. We did rent a boat to go snorkeling and fishing...
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    About this property
    Village of Islamorada VR-110 Beautiful two story home ......four bedroom three baths.....on your private white sandy Beachfront property with large pool facing the ocean. First floor is independent with a very large one bedroom, bar with wine cooler full bath, living, dinning and new kitchen....
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    Matecumbe Key, Florida Keys 33036
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the spectacular view of the Florida Bay from either one of the TWO balconies in this 2 story townhome, located off the master bedroom or the living room. Amenities include Wi-Fi, TV's in the living room and master bedroom, phone (for local calls), a grill and carport parking! There are tons...
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    Matecumbe Key, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this...
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relaxation at its best awaits you in our beautiful, Keys townhome on mile marker 87. Executive Bay Club is located in Islamorada, the Sports Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a heated swimming pool, a clubhouse, a private beach...
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    Matecumbe Key, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Terrace
    • Cable/satellite TV
    • Parking
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days  'Crystal Clear Bay Home' offers beautiful open water views and fabulous world famous sunsets. This brand new home is located at Mile Marker 89 on a quiet street in Islamorada. Everything is brand new and offers 4 bedrooms and 2 1/2 bathrooms. Upstairs,on the main level...
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    Matecumbe Key, Florida Keys 33070
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Grill
    • Hot Tub
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. 'Beacon Reef 406' is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient to...
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    Matecumbe Key, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    BEACON REEF 5221 / 28
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Beacon Reef and Islamorada was beautiful. The condo was spectacular and the ocean front view amazing. The condo had a beautiful pool, dock, beach and gym! In terms of...
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    About this property
    Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. 'Beacon Reef 522' offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy with your choice to stay here....
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Islamorada Yacht Life1 / 23
    (2)Terrible
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Best seen by the water Islamorada is yours to explore from this fully appointed yacht. 4 bedrooms one king and 3 with two single beds each make this an ideal spot for a family gathering, romantic getaway or corporate retreat. Luxe island decor abounds and there is ample indoor and outdoor...
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Grill
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated on the beautiful Florida Bay, this 3BR/2BA Islamorada home offers an idyllic waterfront haven with its own private beach, dock, kayak, paddleboards, and sprawling backyard with a volleyball net. Spend leisurely afternoons fishing off the dock before cooking up your catch on the grill....
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and relax at our beautiful 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 fishing/boat dock. This...
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1 bedroom/1 bath condominium is located in Summer Sea in Tavernier. This is a gated complex located directly on the Florida Bay at Mile Marker 88.5, which is within the Village of Islamorada. The unit has a stunning view of the bay from the living room, master bedroom and the balcony. It...
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Directly on your private oceanfront beach. Ocean views from every room of your two bedroom one bath Keys style duplex villa.You will experience the true 'old Keys' charm of bird watching on the wraparound deck to fishing on the beach...or perhaps just relaxing on the sand.With over a half acre of...
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming canalfront home in prestigous Venetian Shores. A simple yet lovely, ground level 3 bedroom, 2 bath home with direct access to ocean and bay via Snake Creek. With 70 feet of dockage, a fish cleaning station, gas grill, and great outside patio, this home is a fisherman's dream. Enjoy your...
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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