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Florida Keys Wheelchair Accessible Holiday Rentals

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    Travellers to Florida Keys are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    44 Matching Rentals in Florida KeysView all 1,506 rentals
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    Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage1 / 38
    (40)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Ocean pointe  island retreat1 / 23
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Oceanfront Condo - Pool, Beach, Tennis & Marina1 / 56
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Spacious Top Floor Condo w/ Water View!!1 / 33
    (9)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2018
    The view is far more than just spectacular! The marina below is well maintained and makes sitting on the lanai a dream as there is always activity to watch. As for the unit...
    Reviewed 28 August 2016
    This was our second stay at this property. We loved the condo first time around and it was even better for this stay with improvements to the condo and all building works...
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    About this property
    Top floor suite! Beautifully furnished condo overlooking the aqua-blue waters of the Gulf of Mexico! This 1,700 sq. ft. , custom decorated condominium offers a unique water vista from the living areas. The split floor plan provides privacy as the bedrooms are on each side of the living/dining area....
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    Marathon, Florida Keys 33050
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Newly refinished  condo open water views very nice1 / 16
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 February 2019
    Apartment was very clean and nicely decorated. Mark has thought of everything his guests might need. The complex was amazing with a great pool, tennis and paddle board courts...
    Reviewed 13 January 2019
    We were unfortunately unable to visit this condo & islamorada due to an unforeseen medical emergency. The condo owner was very gracious & for that reason alone, I would...
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    About this property
    Beautiful professionally decorated superior condo in the best location in Islamorada. The unit is superior with the best water views, with everything you need ,full kitchen stocked with cookware, microwave, coffeemaker, large island counter, breakfast nook with ocean view, washer and dryer in...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean-Front Caribbean Home.1 / 21
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Washer
    • Balcony
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 March 2018
    Very much enjoyed our stay. House was beautiful and clean, staff was friendly and helpful. My mother and I loved relaxing in the hot tub and my father and husband very much...
    Reviewed 24 April 2015
    Rolled out of bed early every day this week with my boys and family friends for my favorite commute: 50 yard walk to a private boat slip at the resort. We rented a boat...
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    About this property
    The Royal Palm, South - Ocean Front Home Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Full kitchen with Subzero appliances and Viking stove. Chiseled-rock flooring throughout. Wrap-around verandas. Seamless curved-glass corner windows. High open-beam ceilings. Located on The...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Key West Florida Beachfront Condo1 / 22
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Sauna
    • Ocean Views
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2018
    Mrs Carol thank you for the beautiful place to stay in for a beautiful trip. The views were awesome from the room. The sunsets you can watch from balcony was dream like. Highly...
    Reviewed 24 October 2017
    I went to Key West with four other childhood friends for a 50th celebration! We booked our week five months prior, and of course hurricane Irma ravaged the Island. We...
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    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Private Beachfront Paradise1 / 45
    (12)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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 14 November 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 24 August 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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Villa Sombrero, Marathon1 / 48
    (1)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Washer
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2019
    Easy access to fishing areas, Boat worked fine.Plenty of space for everyone.Large family group from Syracuse NY, Seattle Wa, and Kissimmee Florida.Had a great...
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    About this property
    Villa Sombrero is an exclusive and private waterfront destination in the heart of the fabulous Florida Keys located in Marathon. This unique retreat is perfectly positioned overlooking a natural preserve on a serene protected deep waterway; providing the discriminating yachtsman or sport fisherman...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Oceanfront 2 Bedroom 2 Bath Condo Key West Florida1 / 68
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Waterfront
    • Sauna
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2019
    Thank you for the privilege of renting your Key West home. The unit was exceptional and LaBrisa was exquisite in every way. We could not be happier with our vacation rental. I...
    Reviewed 2 April 2019
    This was an excellent set-up for two parents traveling with two kids. Plenty of space, a very well-equipped kitchen, and we loved waking up to an ocean view. It's about a...
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    About this property
    The 'SeaJay' at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bayside Condo, marina, pool and beach1 / 35
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Balcony
    • Terrace
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2018
    We recently rented this condo unit for a week for our family of six. It accommodated us great, 3 bedrooms plus a pull out couch. Outside was beautiful, very clean and well...
    Reviewed 13 March 2018
    Love staying in this condo was our second year hoping to return next winter if available. already made request.. I would never leave if it were up to me but the location and the...
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    About this property
    Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    THIS IS IT! Magnificent Oceanfront Paradise!  WE ARE OPEN!!1 / 17
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2018
    Great vacation. Received the much needed peace/quiet for rest that was well overdue. Room clean and relaxing. Visited Key West for a day trip while here and had a great time...
    Reviewed 2 June 2018
    The condo was fantastic, clean and with great facilities. The pool was excellent and fellow guest very friendly. The owner was in touch throughout our stay and could not have...
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    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 2-5 people. , large pool on the ocean, . many water-front restaurants and bars nearby. Oceanfront mm 90, Plantation Key. Books up very quickly. Reserve early! Note: We are licensed in Islamorada:...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Reel Paradise - Big Pine Key1 / 17
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Waterfront
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2017
    Very nice house.Everything is kept immaculate.The house is very roomy and well stocked.The grounds are beautiful.There is a nice spot to relax or cookout by the canal.The owner...
    Reviewed 5 August 2015
    This is a great place to enjoy the lower keys. Extremely clean and well appointed. We stay there as often as we can. I can't wait to go back.
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    About this property
    REEL PARADISE, located in Big Pine Key, Florida Keys offers a large open format Keys retreat with vaulted ceilings. 3 bedrooms – King bed master suite – Queen bed master suite and two full beds in a spacious third bedroom, 3 baths, large kitchen, dining room, family room, sitting area, large...
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    Location Information
    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    • Parking
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2018
    Great location!!! They supplied many extras beach chairs and beach towels. Loved that they had bikes right at the condo. We would definitely book this condo again
    Reviewed 22 June 2017
    Great place to stay. Wonderful amenities! Would highly recommend. Location is great for beach, Mallory square and Duval Street.
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2018
    I was having trouble booking my reservation online (technicality), and had to call in for help. One of the girls there was able to help me quickly, booked me & took my payment...
    Reviewed 19 January 2018
    Yes there was..DO NOT RENT FROM ITRIP/PHOENIX RENTALS.They were totally dishonest with me. They did not tell me that there was major construction going on in the building I...
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    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
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    Location Information
    Islamorada, Florida Keys FL 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spectacular Atlantic Ocean View Condo (MONTHLY)1 / 26
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 May 2016
    When we arrived at the condo there was construction going on around it and it was a little confusing. However, when we got in the room it was breath taking !! The view is...
    Reviewed 27 December 2015
    This place was awesome. The pictures are not misleading. The balcony is right on the water, You are sitting on the porch with a morning cup of coffee and a great, unobstructed...
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    About this property
    ************************************************************************************************************************ NOTE: We are currently accepting only monthly rentals (28 days or longer). Please inquire for a quote....
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada Luxury Waterfront Condo with Boat Slip1 / 21
    (19)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Waterfront
    • Hot Tub
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2019
    The condo was gorgeous; it is always nice when what your see advertised in pictures is what you get when you arrive at the rental property. Views from the screened in patio of...
    Reviewed 26 February 2019
    This condo is everything and more that you see in the pictures. It's difficult to imagine the view, it's 180 degrees of water - amazing. Gorgeous gated community, immaculate...
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    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club...
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    Location Information
    Islamorada, 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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    • Grill
    • Central Heating
    • Waterfront
    • Ocean Views
    • DVD Player
    • Hot Tub
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BOOK BY NOVEMBER 15 TO RECEIVE 10% OFF YOUR STAY Condo has just been updated to include new mattresses, carpet, paint, linens, pots/pans and dinnerware. You will not find a cleaner unit in such a great location. This unit is in sought after Building #4 which is the closest to the ocean, offering...
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    Location Information
    Tavernier, Key Largo 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Palm Cottage - Upscale, 2BR/2BA, Cabana Club Pool1 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2019
    This house was amazing,the view to our back patio was amazing waking up every day to that view was great. Community pool and private beach was prefect and a walking distance and...
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    About this property
    Welcome to our Key Colony Beach vacation home. We are located at the end of the canal between 8th and 9th streets and enjoy an unobstructed views from the kitchen, sitting area, dining room, and living room directly down our beautiful canal. Our home is bright, much wider than most with twice the...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Vista at Ocean pointe1 / 22
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Ocean Views
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2019
    We booked via AirBNB. George was great to communicate with. The condo is exactly as it appears. The pool area was pretty packed on the sunniest days so get there early! If...
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    About this property
    Direct ocean view from your kitchen and living room. Fully updated unit featuring granite counters and stainless appliance in kitchen. the two bathroom feature Walk In showers with frameless glass doors and tile and granite sinks. The master bedroom separate bathroom with king size bed. The second...
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    Location Information
    Tavernier, Key Largo 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    • Internet Access
    • Washer
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Caribbean Conch is a fantastic rental with a great location in the 1800 Atlantic Condo Complex. This unit features an extra large floor plan, both bedrooms and the living room have impact resistant sliding glass doors that open on the a large wrap around deck, you may even get a glipse of the...
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    Location Information
    Stock Island, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elegant, Two Bedroom Condo Close to the Ocean1 / 19
    (17)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 February 2019
    The condo was very nice. Clean and roomy! We had a wonderful time. Check in and out was simple and all directions were spot in
    Reviewed 6 November 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
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    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Hot Tub
    • Washer
    • Balcony
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    • Cable/satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LAST MINUTE DEAL FOR NEXT WEEK (JAN 13-20, 2018). RATE DROP OF $200 FOR THE WEEK. BASE RENT IS NOW $1400. The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Waterfront
    • Ocean Views
    • Wi-Fi
    • Cable/satellite TV
    • Children's Pool
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome from Sally and Andrew We look forward to sharing warm tropical breezes and beautiful clear turquoise seas set amid our little slice of Keys Paradise. Feel a sense of Life, Light and Love in our modern, spacious and well maintained Home. Set in an Oceanside location, surrounded by Breezy...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West. For anyone with an affinity for the sea, everywhere you turn is a reminder of the water – from sailboat replicas of every shape and size; prints of fish and sailor...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Cozy Couple Getaway! or Great Family Home1 / 15
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Internet Access
    • Private Garden
    • Washer
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2016
    My spouse and I are caregivers to a 3 yr old boy who was abandoned by his mother. The stressful situation was reason enough for us to get away for a few days. We selected this...
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    About this property
    Great 2/1 house. Completely renovated. Full kitchen with new stainless steel appliances: Microwave, Range/Oven, Dishwasher, Refrigerator. Central A/C & Heat. Master bedroom has queen size bed and a 32' flat screen tv. Second bedroom has a full size bed and a twin size trundle (full sleeps 2 and...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Key West's only Real Beach House1 / 11
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 April 2017
    Words will never be able to convey how beautiful, tranquil, peaceful, and perfect Sea Vista Estate is. I am literally "homesick" to go back, and we've been home a mere...
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    About this property
    Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully furnished...
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    Key West, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Sauna
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    • Waterfront
    • Hot Tub
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    GALLEON RESORT OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY VIEWS OF KEY WEST HARBOR, SUNSET KEY AND THE GULF OF MEXICO. (These views are also available from the master bedroom, living area and kitchen all day, every day) 4th FLOOR OCEANFRONT...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Ocean Views
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    Pet friendly
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    Smoking allowed
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    WATERFRONT PENTHOUSE with LOFT / 2BR/2BA + GREAT VIEWS OF THE MARINA, OCEAN & HISTORIC SEAPORT 5th FLOOR CONDO RENTAL w comfortable high ceilings / Sleeps 8 / 1 Master King - 2 Guest Room Twins - 2 Loft Twins - 1 Queen pullout / Private Balcony EXCEPTIONAL LOCATION & CONVENIENCE On the ocean at...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4/3 Gorgeous, Private Home w/open Bay & SwimSpa1 / 82
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Waterfront
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2015
    We had never been to the keys before and took a chance on renting this house. It really was a great place for us. We were a party of 6, my husband, myself, our two adult sons...
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    About this property
    Stay in this spectacular open bay front home and fall in love. You'll never want to leave... All the comforts of home are provided while you relax and enjoy swimming, fishing, boating and more in your own backyard. For an even more entertaining and relaxing vacation, we have an Aquatica 10 Swim...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING VIEWS OF KEY WEST, SUNSET KEY AND THE GULF OF MEXICO Sleeps 6 / 1 Master King - 1 Guest Queen / 1 Queen pullout / Private Balcony EXCEPTIONAL LOCATION & CONVENIENCE On the ocean at the end of North Front St (literally steps from your...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Duck Key Vacation Rentals! Located on a private island in the Florida Keys, our Duplex is the perfect spot for your next vacation! Within walking distance, you’re only minutes away from many outdoor activities like fishing, diving, snorkeling, dolphin encounters, sailing, parasailing,...
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    Location Information
    Lower Keys, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps eight people. Master bedroom has a king bed with access to the balcony. Second bedroom has a queen bed and third one has two twin beds. TVs in every...
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    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Children's Pool
    • Washer
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very large, Islamorada, waterfront, pool home with plenty of room for everyone on Lower Matecumbe Key in the heart of the Florida Keys. The house has a total of 10 beds in 7 bedrooms and comfortably sleeps 14 guests. The house is 3 stories, with an elevator, and has over 4,200 air-conditioned...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • Waterfront
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    • Cable/satellite TV
    • Sauna
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    AVAILABLE FEBRUARY 5-12, 2018 SLEEPS 6 Charming vacation destination that will give you a lifetime of good memories. Idyllic combination of clear, azure waters,bright Florida sun, some of the best salt water fishing anywhere. Clean and comfortable, dozens of restaurants. Have a drink at the Tiki...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Hot Tub
    • Waterfront
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A spacious, airy 3-bedroom, 3-bathroom penthouse at The Galleon Resort & Marina in the Old Historic Seaport in Key West. Available from Saturday March 31 to April 7, 2018. Weekly Rental Only. The first level of the penthouse has a full kitchen and wet bar, with a washing machine and dryer. There...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous Bay front condo and newly updated. Kitchen has ungraded cabinets, granite countertops and stocked with everything you should need to make a gourmet meal. Two bathrooms also with upgraded cabinets and granite. Large bedrooms with a king bed in the master suite and two queen beds in guest...
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    Location Information
    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located one hour from Miami, Florida... the Kawama Yacht Club is your escape route to the Florida Keys. Situated at mile marker 100 on the Atlantic Ocean, this gated community offers all you need for a relaxing vacation or getaway. Enjoy the panoramic view this 5th story unit has to offer of the...
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    Location Information
    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 29 DAYS - Available this winter! Very comfortable 50ft dock, wide canal, home located close to Tavernier Creek Channel with easy access to the Gulf and Atlantic. Great fishing, kayaking and diving. Concrete dock, fish cleaning station . 1.5 mile north of the world famous Holiday...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Balcony
    • Air Conditioning
    • Secure Parking
    • Housekeeping Included
    • Cable/satellite TV
    • Terrace
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 2 bedroom 2 full bath ocean view condo steps away from the Atlantic Ocean. It is located on the island of key colony beach, just minutes from marathon. Our unit has a large balcony accessible from the master bedroom and the living room. It is located just 3 units back from the ocean with...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully furnished 2 BR 2 BA Condo on second floor.(First is parking only) Spiral Staircase directly down to lushly landscaped grounds. Only this floor has the stairs, others have to go through a lobby with a key. Wander around among our beautiful tropical gardens, bring your drink down to the...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Islamorada 2-bedroom Condo1 / 6
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Waterfront
    • DVD Player
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    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 November 2014
    Just wanted to thank Bill for a wonderful four days at his place. Condo has tremendous views -- you are on the top floor -- amenities are great as well as the sleeping...
    Reviewed 7 July 2014
    The pool is sparkling clean. You can enjoy the ocean-view from the pool area. The balcony is a wonderful place to hang out and relax. Close to everything.
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    About this property
    If you’ve been to Islamorada you know it as the sportfishing capital of the world, a place where you’ll find every water-related activity imaginable, with fine restaurants to crab shacks serving local fare, and plenty of nightlife for both the young and young at heart. If you’ve never been here, a...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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