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Florida Keys House Rentals

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    Travellers to Florida Keys are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    926 Matching Rentals in Florida KeysView all 1,528 rentals
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    Escape to Paradise in a Gated Tropical Bayfront Estate (Free Wifi)1 / 19
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Blue Bungalow in the Florida Keys1 / 24
    (7)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    4 Bedroom 2 Bath With Ocean View and with hot tub1 / 140
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Private Island Rental with 19' Boat, Seabird Key1 / 51
    (11)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2016
    Seabird Key was absolutely perfect for our family. We were were a party 4 adults, a 2 year old and an infant. The island was well-suited for all. We enjoyed going to the beach...
    Reviewed 19 March 2015
    Wow. Seabird Key is one of a kind. We felt like we were in the swiss family robinson movie. The house's main floor is perched at the same level as the tree canopy. If you...
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    About this property
    Seabird Key is a ten acre private island available for rental by the week featuring an architecturally stunning home with gracious porches and multi level decks; a private, sandy beach and beautiful, tropical gardens throughout. Only 5 minutes offshore by boat, this is the Island that has it...
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    Marathon, Florida Keys 33156
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    82754 Overseas Highway1 / 29
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    We have been staying in the keys for 5 years in a row & this was the best rental property we found. We are 4 guys (over 50) who want to go fishing and relax and this property...
    Reviewed 9 May 2017
    Our family (three generations) wanted a place in Islamorada with 5 bedrooms. We rented the Osprey Bay Villa for a week and it was a perfect fit. The bay side location provided...
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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...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning Atlantic Ocean views from dining area, living room and both bedrooms. Sunrise on the left, sunset on the right and in between 180 degrees of open ocean. Our vacation home is located in exclusive Summerland Key (mile marker 24.5). Whether you are daring adventurer or a more indoor type of...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Want to be close to the Mainland while still being in the Upper Keys? Look no further. This beautifully decorated condo at Moon Bay will not disappoint. The Master bedroom has a spacious King size bed. Guest bedroom has 2 twin beds and there is a bonus room with a trundle bed. Vibrant colors...
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    Tavernier, Key Largo 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Waterfront two Bedroom Paradise Villa with Pool WF 1a1 / 24
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2017
    Took me a while to write this reviewOh!!!still missingWe loved this pkace , the cleanness, the privacy , the confort and. ..the LadiesThank yu so much. For this placeWe had a...
    Reviewed 27 June 2017
    I have walked into a spotless most beautiful rental property I have stayed in. Everything you want to do from dinning, boat rentals and kayaking is so close from home. You...
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    About this property
    Charming doesn't even begin to describe this modern, tastefully appointed waterfront 2 bedroom 2 bathroom house. Plush bedding, upgraded kitchen and bath, and a breezy terrace perfect for bbq's and relaxing. This home features a private pool, and dock and direct canal access to the open water....
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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We survived Hurricane Irma and these pictures were taken after the storm. Discover the Ease of Booking a FL Keys Vacation...Welcome to Sachs' Sea Shack…Bayside Deep Waterfront Pool Vacation Home with 60 feet of Dockage in Marathon, FL, the heart of the Florida Keys. A newly renovated 2 bedroom...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Gorgeous Waterfront Home, Free Wi-fi &Private Dock1 / 34
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Internet Access
    • Patio
    • Washer
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2017
    The home is wonderful. Everything like new & well equipped. The owner, Arianna, is most accomodating & quickly responds to messages. We appreciated the supply of...
    Reviewed 6 April 2016
    This home has everything you need for a Florida Keys vacation. We selected the location on the north end of the Keys so we could have easy access north to Miami. The home is...
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    About this property
    Welcome to Paradise Point, a beautiful private community in sunny Key Largo! In this private and secure gated community of just 32 homes, paradise awaits you! In our home you'll be right on the water with a gorgeous view of a deep-water canal that has easy access to open water. We are located...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Paradise In Marathon, FL Keys Large Oceanside Home1 / 44
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2017
    We enjoyed our stay in this private home right in the heart of Marathon. It is within walking distance of the Cracked Conch restaurant which serves up great local fare and the...
    Reviewed 22 March 2017
    We had a great time staying at this house! Very comfortable for 7 people and the location was nice and convenient - close to supermarkets, restaurants, beach, etc. The owner...
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    About this property
    This house has everything! You can rent 1/2 or the whole house. The top unit has 2bd/ 2bths. Lower spacious unit has 1bd/1bth. Enjoy dinner on breezy upper or lower outdoor patios. This house is more convenient and offers much more than your ordinary 3/3. Each unit is very spacious, sleeps up to...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Catherines Tropical Paradise - 3 Bedroom 2 Bath1 / 33
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 May 2017
    My husband and I really enjoyed staying in Catherine place for our 31st anniversary. Good fishing in Marathon, and mid way in the keys make it a short drive either direction...
    Reviewed 8 August 2016
    The house was spacious and comfortable. Beaches, restaurants, grocery stores, etc. were all a short drive from the house and easy to get to. The rental is a good value for the...
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    About this property
    Stay at our Marathon Key Vacation Rental House in the heart of the Florida Keys. Vacationers find great tarpon, dolphin, sailfish, and snapper fishing, coral reefs and wrecks for scuba diving. Marathon is situated at the mid-point of the Florida Keys island chain, which is why locals have declared...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Beachfront Home w/Heated Pool+45' Dock1 / 41
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Secure Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2017
    When we arrived we were immediately impressed with the house, the rooms are beautiful, beds are comfortable, kitchen is fully stocked with anything you would need for cooking...
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    About this property
    Beautiful Beachfront home located directly across the street from famous Sombrero Beach. Sombrero Beach is surely one of the stand-out beaches in the Florida Keys. This gorgeous beach has something for everyone. Kayaks, boating, fishing & biking all easily available for great fun in the sun. You...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Home in the heart of the Florida Keyes. Come relax and enjoy the beautiful pristine waters of Sombrero and Bahia Honda Beaches. Both nearby. If you’re an Angler, this is the place to rent. There is plenty of room and comfort in our 4 bedroom, 3 bath home. Luxury King Tommy Bahama Master...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    AVAIL: March 31 + for 6; 2BR + 2BA; CC POOL + PRIV. INCH BEACH; 30' Dk; NO pets!1 / 44
    (94)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Ocean Views
    • Washer
    • Waterfront
    • Wi-Fi
    • Housekeeping Included
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    This was the third time we've rented this house and as usual it was great. They updated some of the outdated furniture, which was a nice surprise. I can never say enough nice...
    Reviewed 18 May 2017
    Seriously, if you are looking for a place in the Keys you can stop looking now. I don't know how any place could beat this one. The house has EVERYTHING you could possibly need...
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    About this property
    Welcome to 'KEYS OCEAN DRIVE', the BEST rental LOCATION in KCB!!! 2018: $ VARIES (c/i Sat.-c/o Sat. ONLY!) • JAN. 13-MAR 30 BOOKED • MAR 31 and beyond available, call or email for price (per calendar: 5/12-19 + 5/26-6/2 c/i Sat.-c/o Sat. booked/NA)! We are located ocean side with quick &...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Waterfront Paradise with a heated pool and full dock in Marathon key, Florida1 / 18
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 April 2016
    Spent my 20th anniversary/birthday with my wife and childhood friend and his wife. The house and location was everything we hoped it would be. Rented a boat and parked it at...
    Reviewed 1 May 2012
    We stayed at Boot Key Retreat in April 2012 and it just could not have been more perfect.Marathon Key is a great location, central to the northern island (Islamorada) with...
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    About this property
    BOOT KEY RETREAT === OPEN WATER VIEWS SHORT EASY ACCESS TO OCEAN or Bay with Lobster, Dolphin, Wahoo, Sailfish, Amber-jack, Grouper, Snapper and Tarpon all close by. FISHERMEN, DIVERS and FAMILIES---This is the place you are looking for! This-port-of call is located at the base of...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    'SANDY BEACH' Key Largo,Fl. Luxury Vacation Rental1 / 31
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2014
    This place is truly amazing! The beach is clean and the good sand extends out into the water. The amenities are endless in the house. Kids loved the pool as it gave them a...
    Reviewed 15 March 2014
    My family of 7 including 2 babies just had a wonderful week at Sandy Beach. The house is perfect for a groupwith large quiet bedrooms. The outdoor kitchen and beautiful private...
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    About this property
    Welcome to 'SANDY BEACH' in Key Largo, Fl. Enjoy amazing sunsets from your own private white sandy beach and swaying palm trees that leads you into the warm ocean blue waters of the Florida Bay. This gated 1 acre 3/3 pool home has been updated and beautifully decorated. It can sleep 8 to 10...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Private Pool & New Dock on Deep Canal - winter season open!1 / 23
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2017
    Spent our week family vacation here. Fresh, clean and adorable cottage. Although on the smaller side the yard is excellent and larger than most with plenty of shade. Access to...
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    About this property
    Come enjoy the Keys Life in the single best location in all of the Florida Keys. 'Miloh's' has been completely renovated in 2016 and just entered the rental market. Dock your boat in the large deep water canal and cool off in your private pool. Enjoy the built-in underwater bar stools in the pool...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    This townhome at Executive Bay will sure make your home away from home!  This unit has been completely renovated and decorated beautifully.  This  2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 6
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    Coral Hammock - Comfortable 3 Bedroom Home1 / 15
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Terrace
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2017
    Great times in key west coral hammock is about a fifteen minute drive to duval street. The place is real nice and quiet a lot of space for your whole group. Great trip all...
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    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Islamorada Waterfront Paradise Getaway!1 / 28
    (31)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    We spent a wonderful, spirit rejuvenating MONTH with Ewa and Peter at their beautiful home by a lagoon in Lower Matecumbe Key. At first we bustled about, kayaking from the dock...
    Reviewed 1 March 2016
    We had a delightful stay in this lovely property - by the water and with hammocks and a very peaceful setting. The room was well equipped and the owner were very helpful.
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    About this property
    Please contact us for all of our rates for different length of stays! For shorter stays...make sure you have a minimum of 28 days entered in your contact form! DO NOT BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you significant FlipKey booking...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
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    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this your Key West Vacation home! Cozy 2 bedroom, 1 bath home set on the back half of a residential lot with new kitchen, bath, and furniture. Privacy provided by the fenced outdoor area, with a shaded porch and furnished gazebo for relaxing. The location is 5 minutes max to anywhere on the...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'The Beach Fixes Everything'. That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully decorated, extra clean, new furniture, fully equipped kitchen brand new hot tub, along with everything you will need to make your stay comfortable. Walking distance to one of the most beautiful beaches in the Florida Keys. Only minutes away from the 7 mile bridge where you could walk...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    500 Ocean - Tropical Florida Keys Vacation Home1 / 70
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2017
    Location, location, location - fishing, beaches, access to wonderful attractions-what else could you ask for? Oh, how about a stunning home in a lovely, quiet neighborhood. We...
    Reviewed 8 June 2017
    We stayed at 500 Ocean during a short trip to Marathon. The home was clean, the beds were comfortable, and we had a beautiful patio to hang out on at night. We were able to...
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    About this property
    500 Ocean is truly a great value and sells out quickly. We provide luxury level setting in a Coconut Palm Paradise for a great fishing, diving or relaxing family value vacation in Marathon Key Florida. This place is really a Coconut Palm paradise, it is like living in a Palm Tree house with all the...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This tropically decorated 2 bedroom 2 bath unit, has a King bed and (2) Twins beds is approximately 1 hour and 20 minutes from Miami International Airport and 90 Minutes from Ft. Lauderdale airport.  Futura Yacht Club is located in the Village of Islamorada in the Upper Florida Keys. Located...
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    Location Information
    Tavernier, Key Largo 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    **Spring Discount** Family Friendly Executive Bay Townhome with Beach & Pool1 / 25
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2015
    We attended with my wife and adult daughters and this apartment had everything we could wish for.The facilities were ideal for our needs and the booking process was simple.Due...
    Reviewed 13 September 2015
    The condo is very nice and spacious for 5 persons. The place is clean and supplies are adequate. Location is good. Swimming pool is big and nice. Able to do a little fishing...
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    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Come and relax at our beautiful town home on mile marker 87 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...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This magnificent home with direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Lie in bed and view the Ocean! Home also overlooks the community pool. Anglers Reef is a quiet oceanfront...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Smoking allowed
    About this property
    SuCasa is located next to Robbie’s Marina where you can hand feed the Tarpon on Lower Matacumbe. The Main House sleeps eight comfortably in four bedrooms with 3 queen-sized beds and two twin beds and comfortably sleeps 8. It has a fully equipped kitchen with a stove, dishwasher, microwave, coffee...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    This unit's kitchen, bathrooms, windows, and doors received a facelift in January 2014! 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, flat panel TV's in...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    KWO - 2 BR/2 Bath, Private Pool, Separate Cottage1 / 23
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Recently spent 10 days at KWO. This property is superb and reflects a pride of ownership. KWO clearly exceeded the already impressive presentation on the website. Paula and...
    Reviewed 15 August 2017
    Great location in Old Town, away from Duval Street, but still within walking distance to great restaurants and Duval if that's your idea of fun. The house has everything you...
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ocean Side Villa  in Exclusive Key Largo Community1 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Internet Access
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    • Patio
    • Waterfront
    • Washer
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 March 2015
    Very comfortable home but not with very young children-glass table tops and white carpeting.Easy walking distance to pools and other amenities. Some distance from Key Largo and...
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    About this property
    213 Andros Road Welcome to the Ocean Reef Club! 213 Andros Road is a 1950's cinder block 3 bedroom 2 bath home in the elegant and exclusive Ocean Reef Club in Key Largo. 213 Andros is a 5 minute walk from the club's central facilities which include the main restaurant, gift shop, pool, tennis (14...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada Tropical Canalfront Paradise1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Wow! This property is just perfect for a quick getaway! The backyard was so fun, for our entire family. My kids loved the hot tub, my wife loved the waterfront view and I loved...
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    About this property
    The moment you step in the back yard, you'll know vacation has begun. . . time stands still as the laid-back island lifestyle takes over...Totally remodeled, canal-front home, quiet and in the nicest of neighborhoods (Plantation Key Colony). The 2 bed/2 bath stilted (upper level) island retreat is...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Outdoor Dining Area
    • Porch
    • Secure Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful fully furnished 2/2 home located on Ocean front canal in Key Largo. Kitchen completely remodeled in 2018. Unit is located in the best Community in Key Largo. Less than 100 yards via boat from open Ocean. Beautiful grounds, boat ramp, and plenty of parking. Great views and plenty of...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Key Colony Beach Griffins' Getaway1 / 27
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    • Waterfront
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2017
    The minute we walked in the door,mew felt comfortable, the house was bright and cheery, and very clean. Lucille did a great job decorating and provided a very comfortable home...
    Reviewed 19 June 2017
    The place was clean, comfortable, and had everything we needed for a wonderful time. We were in constant communication with the owner who obviously takes great pride in the...
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    About this property
    Key Colony Beach Canal Front Property. Nnew deep water boat dock (37.5 ft) directly at your back door with a fish cleaning table, water and power on dock. bait freezer 5 min. boat ride through the 100' wide canal leads toVaca Cut and the Atlantic Ocean and quick access to the Gulf of Mexico...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,800...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 3 Bathrooms, Sleeps 2 Quick View
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    About this property
    Sweet little home away from home. This 1 bedroom 2 bath condo hosts beautiful views of the Atlantic Ocean. Sit on your back patio and watch over the marina or for those early risers watch an unforgettable sunrise from your 3rd floor balcony. If you are looking to get out on the water the complex...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 1 Bedroom, 3 Bathrooms, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
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    Smoking allowed
    About this property
    Canal front home with a pool that has 2 bedroom 2 bath upstairs and a 1 bedroom and 1 bath downstairs.  The home has a lot of great space to sit back and relax. Worried about cooking food?  Off the living room there is a nice seating area on the balcony.  Don't be this home has a full kitchen...
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    Tavernier, Key Largo 33036
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Paradise n Summerland Key Cove1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2016
    Whatever I'd hoped for, this vacation home has without question, surpassed any and all expectations! Excellent location; in a quiet and beautiful strip. Loved relaxing on the...
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    About this property
    Amazing canal front 3 bed 2 bath open concept house located in prestigious community of Summerland Key Cove. It is the first canal from open water and one of just a few flow-through canals providing excellent water quality. The canal is deep and wide. Expect to see lobsters, crabs and other sea...
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    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Sweet little home away from home. This 2 bedroom 2 bath condo hosts beautiful views of the Atlantic Ocean. Sit on your back patio and watch over the marina or for those early risers watch an unforgettable sunrise from your 4th floor balcony. If you are looking to get out on the water the condo...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Waterfront Home in The Fabulous Florida Keys!1 / 22
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 November 2016
    We couldn't have been happier with staying at his home in Big Pine. The view from the upper deck is beautiful and everything we expected when we rented the home. It's about 40...
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    About this property
    PEAK A BOO BAY VIEWS & QUICK ACCESS TO THE OPEN WATERS; GULF & OCEAN. Very Clean 2 bedrooms, 2 bath home with over sized master bdrm & bath. Cathedral ceiling in spacious living room that includes a queen size sleep sofa. Home is bright & airy. Wide, open covered deck with wrap around walkway....
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    Location Information
    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key Largo Villa - Beautiful Waterfront 3/2 + Den1 / 26
    (6)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful, waterfront house in Key Largo is our 2nd home. We are currently only looking for mid-to-long-term rentals (min. 3 months) beginning April 1. Enjoy watching breathtaking sunsets over the Bay from the 2nd floor balcony. A short canal leads you to tranquil Sexton Cove, with ocean...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ocean front paradise with 95 feet of ocean frontage. Exotic natural serene setting with easy ocean swimming and access. Customer responses equate it with a resort atmosphere and very unique dense fauna sheltering trees, flowers,and visits frequently by humming birds, tree frogs and the like....
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    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    YOUR PRIVATE GETAWAY IN KEY WEST, FLORIDA.  This beautifully historic 2 bedroom 2 bath home is conveniently located in Old Town Key West, FL. Just a short walk from everything you could dream of, for your island vacation. Just 5 blocks from the famous Duval Street. Two blocks from the seaport,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
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    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Keys home in Anglers Reef with ocean view, dock, community pool & private beach This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    About this property
    This lovely 1 Bedroom 1 Bath Condo is only about an hour and fifteen minute drive from Miami International Airport and about 90 minutes from Ft. Lauderdale in the Village of Islamorada, the 'Fishing Capital of the World.' The unit offers sea breezes and ocean views. Seagulls condo offers a...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Dream Vacation House1 / 12
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • DVD Player
    • Wi-Fi
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    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed yesterday
    This house has everything: large main bedroom with huge balcony over the bay, 2 large bathroom, large living room with kitchen and dining room, a place to get shade, a place to...
    Reviewed 9 November 2016
    House was very clean. Location was near parks, shopping, restaurants. Saw dolphins and manatees in canal behind house.
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    About this property
    Our property, private deep water canal dockage. This beautifully decorated home also offer two Association parks with beaches, pavilions and two private boat ramps. Shopping and fine dining nearby. Easy ocean and back country fishing from our back yard. Key west is a short scenic hour and half...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    This newly renovated and remodeled 2 Bedroom Condo is only about an hour and fifteen minute drive from Miami International Airport and about 90 minutes from Ft. Lauderdale in the Village of Islamorada, the 'Fishing Capital of the World.' This unit is comfortably and stylishly furnished, it has(2)...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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