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Florida Keys

Pet Friendly Holiday Rentals in Florida Keys

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    Travellers to Florida Keys are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    487 Matching Rentals in Florida KeysView all 1,453 rentals
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    FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 8 w/ 60 Feet of Dockage1 / 27
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Blue Bungalow1 / 14
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access1 / 27
    (18)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 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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    • 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
    PARADISE OCEAN FRONT HOME1 / 38
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • DVD Player
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2019
    We loved the house! Plenty of space, clean, great location! The owner was quick to reply to answer questions and even recommended a great sandbar to take the boat out to. We...
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    About this property
    Beautiful and completely remodeled home only 4 houses from open ocean on the Atlantic side of Marathon. This cozy home features 4 bedrooms, 3 bathrooms with lots of natural light and open floor plan style living room and kitchen and stainless steel appliances. Two of the bedrooms are MASTER SUITES...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Confortable and spacious, 2 bedrooms 1 baths. Home is in a residential fishing village. Full house is actually a 3/2, split master suite. Rental increase $35 per night for the full 3/2. Trailer parks in the neighborhood, like most of the Florida Keys, but the home is not a trailer. The housekeeper...
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    Pigeon Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Paradise In Marathon, FL Keys Large Oceanside Home1 / 22
    (7)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
    Waterfront luxury Villa (54) with sunset views and boat slip1 / 15
    (7)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Parking
    • Terrace
    • Cable/satellite TV
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 January 2017
    Each summer our family attempts to find that perfect spot in the Keys for our family of 5. We have stayed many places, Ocean Reef Club, Hawks Cay, Tranquility Bay...each had...
    Reviewed 28 February 2016
    My family (2 adults and 3 children, 18, 14, & 12) stayed at this beautiful property Christmas week. It was wonderful. The community is amazing. The location is mid-way...
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Duck Key Paradise1 / 35
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Washer
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2018
    Incredibly peaceful location. We could actually see the stars at night. We had a group of 8 and the accommodations were great and spacious for so many adults. Outdoor living...
    Reviewed 21 September 2018
    House was perfect and spacious for my family vacation. Beautiful pool and jacuzzi over looking the water. Kitchen is fully stocked for cooking if needed. Close to restaurants...
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    About this property
    Canal Front property. This fabulous home is a 3 bedroom 2 bath located in the sought after area of Duck Key. The home is updated and ready for your adventure of a life time. Upstairs you will find 2 bedrooms and 1 bathroom. The kitchen, dining room, and living room are upstairs. Off the dining room...
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    Duck Key, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    SPECIAL FALL RATES, INCL. LABOR DAY - BOOK NOW!1 / 27
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Ocean Views
    • Washer
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2019
    Everything was as advertised plus!! Great use of all the space, the boat lift was a huge plus the pool is a must in July, very relaxing. The kitchen was stocked with everything...
    Reviewed 3 April 2019
    My family and I absolutely loved our stay at this home. It was beautiful, clean and had everything we could possibly need. The private, heated pool had just the right amount...
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    About this property
    This is Keys living at its best! Tropical classy, comfy and private – yet easy access to everything you could want. This 2 bedroom, 2 bathroom home on a quiet dead end street with open views and ocean access (with houses only on one side) in the heart of the heart of the Keys comes 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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    75130 Overseas Highway1 / 19
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2019
    This house is a home. It affords guests the opportunity to gather in a house that provides a large area to come together both inside and outside with a covered/ shaded outside...
    Reviewed 13 August 2017
    We stayed here for a few days and it was amazing. The house is warm and cozy and has all the details you need when away from home. The beachfront is wonderful and can go...
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    About this property
    Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs...
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!1 / 25
    (18)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 January 2017
    My friends and I have traveled to Key West for the past three years and we always rent through KWVR. Each year we have rented a different property however this property is...
    Reviewed 18 August 2016
    Stayed here with friends. The setup was perfect for our needs - one couple and two singles. My bed was very comfortable. The only thing missing in my room was a mirror! The...
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    About this property
    Poolside Paradise Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, a private pool, a furnished patio, two full...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Paraidise with or witout boat1 / 27
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2019
    The house is located a short walk from the famous "Sombrero Beach"! It's so clean and the water so clear, perfect for kids! It's a very peaceful place. You have...
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    About this property
    Deep canal Bring your yacht. Very private bedrooms on both sides. very large balcony looking at the water view. close to restaurants, beach,Public, Kmart,Winn dixie, CVS, Wells Fargo, UPS, Home depot, West Marine & Walgreens walking distance. Beach 10 minutes walking. Safe area. 5 bicycls their,...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 9
    Waterfront in Key Largo, Terrific 1/1 Apt, 2nd Floor, Pet Friendly, Sleeps 41 / 16
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Cable/satellite TV
    • Waterfront
    • Balcony
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 January 2018
    We had a great time. The apartment was as described, very clean. The bed was comfortable and the linens towels etc were excellent. The apartment is located close to shopping...
    Reviewed 23 March 2017
    Terrific pet friendly one bedroom apartment in Key Largo. Super cosy and beautifully appointed apartment very conveniently located for the beach and snorkelling/diving trips at...
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    About this property
    Welcome to 'Largo Lookout'! This fabulous 2nd floor, waterfront apartment is ideal for singles, couples, or a small family. Largo Lookout is a pet friendly vacation rental that offers guests the opportunity to travel with their well-behaved pets. We require a reasonable, pet fee and have a few...
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    Location Information
    Key Largo, Florida Keys 33037
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort1 / 11
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • Waterfront
    • Grill
    • Washer
    • Central Heating
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Ocean view, on a canal, three lots from open water in Venture Out Resort; a safe, gated community. Park your boat or kayak right outside your front door on the canal, or just relax and enjoy your mosaic picnic table and 4 patio chairs, and Weber charcoal BBQ. Only 7 steps up or down to...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Waterfront luxury Villa (34) with sunset views and boat slip1 / 15
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2018
    Great location beautiful grounds wonderful condo everything you need is there will definitely be renting this condo again this was our 2nd year and we are already planning to...
    Reviewed 9 November 2016
    Excellent stay we will definitely be back! Excellent community. Unit was well stocked and very clean! We had a great time!
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Oceanfront Oasis - Pinch me am I dreaming!!!1 / 44
    (5)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2018
    Despite our rainy week in Islandmorada, Sean helded to make our vacation seemless! We had 10 people staying with us to help celebrate my husbands 50th birthday. The house had...
    Reviewed 13 July 2017
    The property manager was super helpful and walked us through the entire house showing us all the nooks and crannies. I must say I've never had someone take close to 45-an hr to...
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    About this property
    ***NOTWITHSTANDING ANYTHING IN THE RATES PAGE THE MINIMUM RENTAL PERIOD IS 7 DAYS*** For the ultimate Keys experience, little can compare to settling into a custom-built home boasting its own private beach. Crafted with pleasure in mind, this luxurious five-bedroom, four-and-a-half bath house...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    Waterfront luxury Villa (43) with sunset views and boat slip1 / 18
    (25)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2017
    My family of 6, 2 couples and 2 ten-year olds stayed in unit #43 for a week. The townhouse was perfect. Everyone had their own space and there was a huge living room for...
    Reviewed 3 April 2017
    Our family had a wonderful stay at indigo reef. It's a lovely place with great sunset views, and Marathon is a good location for exploring the Keys. We liked it so much we...
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Key Largo Rental Fantastic Views1 / 30
    (25)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Ocean Views
    • Waterfront
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2019
    Nice place. Had a boat slip and a golf cart to use. Had a great experience here at norman condo. Norman was great on talking to you and showing us where everything was on the...
    Reviewed 23 May 2018
    We had a great time at this condo. The owner is close by and extremely accommodating. He has gear for nearly every activity you can imagine, all for your use. The condo itself...
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    About this property
    Experience the relaxed lifestyle of the Florida Keys. 2 Bedrooms + Loft (The loft is the 3rd bedroom or general purpose room with 2 single beds and a Large Flat Screen TV. The staircase for it is more of a ladder then formal staircase. Kids and young adults love it. The loft is not for older...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    East Sister Rock Island1 / 16
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 June 2019
    We just spent 1 amazing week on this 360 ocean view paradise island with our family for my 60th birthday Just birds for neighbors Very easy and quick access to the shore by...
    Reviewed 16 July 2017
    I would recommend this rental property any time of the year, great place to be with the family,perfect!
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    About this property
    Enjoy a private island paradise located at MM50. East Sister Rock Island is 1/4 of a mile off the Atlantic Shores off the City of Marathon in the Florida Keys. On the private island sits a dream come true getaway home with 5000 sq.ft of living area which includes a 2700 sq.ft. covered veranda,...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Gulf View Three - 3 bedroom, 3 bathroom, Gulf Side1 / 20
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Children's Pool
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully furnished, three bedroom, three bathroom, landscaped property is centrally located in the Florida Keys, and features a host of amenities complete with magnificent views of the Gulf of Mexico. Conveniently located on 121st Street, Gulf just past Mile Marker 54 in Marathon Florida -...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Ocean Views
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Henry Flagler Slip into the beach lifestyle and leave the daily grind behind when you book your stay at this oceanfront Layton cottage. With a dock, expansive deck, and a stunning beach location, you may never want to leave. With historic roots as the home to the 1900's author, Zane Grey,...
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    Location Information
    Layton, Long Key 33001
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH1 / 61
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Porch
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 September 2019
    Walking distance to Duval street, restaurants, shopping, bars and not far from the beach, quiet from the noise, everything you needed was available in the room except the...
    Reviewed 27 February 2018
    Just how close do you need to be to Duval not be hinder by the noise other places have mentioned - this is the place. It is beautiful, colorful, and comfortable place to wake...
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    About this property
    La Dolce Vita is just steps to Duval Street! 'La Dolce Vita' is beautiful and is a totally renovated condo. Please check out our calendars for availability, photos and video. Everything is brand new from floor to ceilings! 14 foot high ceilings with back lit crown molding in every...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    New Listing Family Friendly1 / 32
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 June 2019
    clean and well furnished. Very responsive owner. Close to downtown Key West.We would rent this place again.
    Reviewed 23 January 2019
    We stayed with two other couples and found this to be the perfect place to stay in Key West. The home was very well equipped and felt like home. Roy went out of his way to...
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    About this property
    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Dolphin Oasis 4bdr/4bth  Pool/hot tub 115' dockage1 / 36
    (23)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2020
    A great place to relax and have fun with the family. It’s like having your own personal resort, a total slice of heaven.
    Reviewed 3 October 2018
    This was our second stay at this beautiful rental that feels like you have your own resort. All the amenities are perfect and the owners couldn't be more accommodating. Highly...
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    About this property
    This 4 bedroom 3 1/2 Bath House has ample sleeping options for every type of family/friend gathering and provides parking for several vehicles. The newly installed heated pool with hot tub measures 40'x 16'. There is a Tiki hut right at pool side for visiting, Canal Side Beach area and Tiki...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Welcome Aboard!  Relax, unwind, enjoy the water! in key west1 / 50
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2018
    Loved Jen and Mitch! Very welcoming! Made everything very comfortable and relaxing! Thier friends and neighbors are very nice and welcoming too! We enjoyed a cookout, a...
    Reviewed 12 April 2018
    My husband and I enjoyed a 3 day stay on the Fat and Sassy. The owners are welcoming and helpful with any questions or recommendations you it need. The marina is perfect, with a...
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    About this property
    Join us in Key West where we are docked at a beautiful Marina. Enjoy all the comforts of home and the added beauty of the Ocean. There are pools and a Waterfront Bar & Grill for your enjoyment. We will be Aboard in the private owner’s suite to make sure your stay is hassle free and exciting....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    SPECTACULAR Waterfront Key Colony Beach Home w/Heated Pool & Dock1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 May 2019
    Great house, outside Paradise with pool and Tiki hut. Tiki hut was great to get out of the sun but still be outside. Privacy outside but still on canal with nice dock. House...
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    About this property
    Exclusive Key Colony Beach home with heated pool and dock, just off of mile marker 53. Enjoy some of the Keys' best fishing. Shopping, groceries and dining are just a short drive away, or venture off to Key West, which is 53 miles south. Or soak up the sun at the sandy beach with tiki hut and...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Key Largo Kampground Vacation1 / 10
    (3)Average
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2016
    My husband and I had a wonderful time. The rental was beautiful. A lot more room than I expected for the money. I would rent again!
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    About this property
    Trailer 1 Bedrooms, 1 Baths, Sleeps 3 possibly 4 if small children. Newly renovated property. 33 foot RV with attached 30 foot A/C enclosure and Tikki. Only Full month rentals between Jan 1 to March 31. New Kitchen with Stainless steel appliances, 3 burner BBQ, 3 TV, free cable, WIFI available...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Gulf View Place w/ Dock, Pool, Kayaks, Sandy Shore1 / 22
    (6)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
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    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 December 2015
    If you like vacationing in a home away from home, Rent My Island is a great choice! We have stayed with them for the past four years and each year has been great. The private...
    Reviewed 4 April 2012
    The rental itself was ok with a wonderful view and sitting area.Ocena current is real strong not very far out so kayaking and snorkeling is difficult. The place itself was not...
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    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This 4 bedroom, 4 bath property is great for family vacations. Less than 30% of all rentals in Marathon are 4 bedroom or larger. HOW MANY PEOPLE CAN SLEEP AT THIS 4 BEDROOM? Our rental license allows up to 10 people to stay overnight. Three of the...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental1 / 38
    (28)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Patio
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    Over the years, we have stayed here 4 times, and each time gets better due to the improvements to the property. The location is perfect and relaxing for folks who like to fish...
    Reviewed 28 March 2016
    This is my fourth year at the property and it has only gotten better. There were some criticism of the deck conditions and lack of refrigerator at the outside Tiki hut. Those...
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    About this property
    Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email me for the application. Weekly vacation rental...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Housekeeping Included
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful brand new three-story home in Key Largo. Built in 2017. Right next to community bathrooms/showers and pool. Inside resort with pool, boat ramp, canal, community party room and friendly environment. Has extended outside parking. Accessible to boats and jet skis. Near Arby's, Sushi Sake and...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
    Waterfront luxury Villa (29) with sunset views and boat slip1 / 17
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Conch Key Villas Unit 1, Quiet, Clean with Awesome VIews in Paradise1 / 19
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2019
    This was our 4th stay at CKV and fell in Love all over again. Greatest sunsets, relaxing venue for reading, napping and outdoor grilling. Peaceful setting but close enough to...
    Reviewed 31 May 2018
    I could write a novel about this place and most importantly the amazing couple that run it. They make me feel at home everytime I am there. Hurricane Irma brought me to the keys...
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    About this property
    If Comfort, Fun, Fishing and Views Are on Your List, Stay Here! We have ground level or second floor units. We provide outside table and chairs, and just around the corner the barbecue grill is located to grill up those freshly caught Florida Keys' lobster or our wonderful assortment of Keys'...
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    Location Information
    Conch Key, Florida Keys 33050
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Fabulous 2 level home - 3/2 each Level - Waterfront Pool Home in Islamorada!1 / 15
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 September 2019
    The layout was perfect for our large family. It has a complete 3 bedroom, 2 bathrooms home upstairs and another 3/2 on the bottom floor. We all came together at night to cook...
    Reviewed 20 June 2017
    We are one of two couples who each have rented a level for the past six winter seasons and we are so looking forward to returning in 2018. The location is perfect-within one...
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    About this property
    Video of inside, outside, surrounding areas and waterways available upon request. Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. Video of house and area available upon request. It consists of Two...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
    Amazing views from this Oceanside Home  on they Tavernier Creek Waterway; New Do1 / 24
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2016
    Here is the bottom line..after about a week of our two month rental we had already rented this home for next year. The location is awesome and fishing off the dock was...
    Reviewed 25 March 2015
    Great House! Big enough for extended family. I really enjoyed the dock and the view of the water. Clean and neat.
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    About this property
    Come and relax at our beautiful oceanfront home on mile marker 90 in the Florida Keys. Our home is located in Tavernier, the Sport Fishing Capital of the World. It is a private, gated home directly on the Tavernier Creek waterway with breathtaking views. PETS WELCOME, BUT only with prior approval...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Incredible Luxury Home with Waterfront!! Paradise1 / 19
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Hot Tub
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 December 2017
    Cannot even express in words how great of an experience my family had! The house is unbelievable, with two apartments downstairs and three bedrooms upstairs. The yard is amazing...
    Reviewed 5 December 2017
    I loved having everyone at one location and with the 3 separate living areas, there was plenty of space! Easy access to a great bike/walking path. Great restaurants just a...
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    About this property
    Lo-Key Estate is truly a luxury Keys home situated on a private 400’ waterfront peninsula with the use of a tropical swimming pool w/waterfall and hot tub(shared w/guest house) There are Ocean Views from the 2 & 3rd floors. Lo-Key is a custom 5 bedroom/5 bath home that opens onto Florida Bay...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelico Paradise At this gorgeous Sugarloaf Key vacation home, you'll have five spacious bedrooms (including two master suites)! Enjoy beautiful Gulf views set over three acres, offering privacy for a memorable Florida escape. It's even dog-friendly! Just 18 miles from Key West, this location...
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    Sugarloaf Key, Florida Keys 33042
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage....
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Patio
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    • Washer
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Magic in Marathon Spend some time in the Florida Keys at this three-bedroom, canalside rental with a furnished and covered patio, private pool, a 75-foot dock, and plenty of room inside the home for up to seven guests (six comfortably). The family dog is also welcome to join you here for an...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok1 / 28
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2018
    We were very pleased to locate this little home with a shared pool in the heart of the historic district. We were a group of 4 so we were looking for a clean, comfortable, and...
    Reviewed 7 March 2017
    Clean, quaint, and comfortable. The office help was great, and cleaning service was good. This is close to all of the action while maintaining a peaceful night's sleep.
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    About this property
    Poolside Retreat Up to four guests can enjoy all the fun of Key West at this updated home complete with a shared pool with waterfall, and lush, outdoor seating area. As an added bonus, this home comes with private, off-street parking for one vehicle - a real luxury in the Keys! Dogs are allowed...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Dog-friendly, tropical escape with central location, hot tub, and shared pool1 / 25
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Patio
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 December 2016
    My boyfriend and I stayed here for 4 nights in October. The house was very clean and the check in process was very easy. The house has a small shared pool with the other condos...
    Reviewed 31 July 2014
    The Flamingo Hideaway is a ground floor unit in a small condo complex of renovated, period buildings. This unit is tucked away from the street and right next to the shared pool...
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    About this property
    Flamingo Hideaway Surround yourself with peace, tranquility, and seaside fun when you book your trip to this Key West cottage. Enjoy the bubbling hot tub, shared pool, and easy beach access. Nestled in the Palm Gardens condo community in Old Town Key West, this tropical home embraces you with...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Gulf View Suites w/Docks, Pools, Kayaks -Sleeps 201 / 29
    (3)Very good
    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This rental offers a great option for multi-family vacationing by providing two 4-bedroom homes side-by-side. This gives you 2 kitchens, 2 pools, 2 deep water docks, 2 gas grills, parking for 6 vehicles and 6 kayaks! These properties are non-smoking...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
    Islamorada Tropical Canalfront Paradise1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Parking
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2018
    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 unit) island retreat is...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Bayfront house w/ ocean views, dock & easy beach access - dogs ok!1 / 40
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Patio
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    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We loved our stay in Marathon. Large deck overlooking a canal with a family of manatees. Walking distance to restaurant with good food, a pool and sunset views. A short drive to...
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    About this property
    The Atlantic Lookout Make your Florida Keys dream vacation come true at this bayfront house with ocean views, a dock, and dog-friendly attitude for a group as large as six to enjoy! Sitting at the westernmost point of Marathon on Vaca Key, you'll have easy access to the shimmering ocean water...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Cable/satellite TV
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    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ninth Street Getaway Make your next vacation one to remember with this incredible canalside home in the Florida Keys! With a private 37.5-foot dock and access to both the Cabana Club and Inch Beach, this dog-friendly duplex has plenty to offer! Your home is right on the canal for easy ocean...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our little slice of paradise on mile marker 106! Come and relax at our beautiful fully updated mobile home in Key Largo, the Sport Fishing Capital of the World. Just minutes from John Pennekamp Park as well as many dining, shopping and grocery options. ** PETS WELCOME BUT ONLY WITH...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Family friendly condo w/ shared pool, hot tub & dogs ok!1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Wi-Fi
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    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Saint Lucia Suite 201 Escape to the sunshine and soft sands of the Florida Keys with this amazing dog-friendly home in Sunrise Suites Resort in Key West with a shared pool. Enjoy bird watching at the Salt Ponds Preserve from the comfort of your private balcony. Back at...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Hot Tub
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Cozumel Suite 112 Wake up every morning to the crisp smell of the ocean when you stay at this cute condo on the shores of Key West! Complete with upscale resort amenities like a shared pool and hot tub, tennis courts, and a private, covered parking space, this comfortable rental is...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Dog-friendly half-duplex w/ a 30-ft dock including Cabana Club pool and beach1 / 24
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2018
    The house was fairly well equipped. Very clean but the furniture in the living room area was not very comfortable. The TV was small and there was none in the master bedroom...
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    About this property
    Sunlit Serenity Go on a Key Colony Beach retreat at this updated dog-friendly home. Enjoy a 30-foot dock, and exclusive access to The Cabana Club private beach, swimming pool, and restaurant. Located right on the water in the popular vacation spot of Key Colony Beach, this duplex home is...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Dog-friendly home w/ private pool - walk to the beach and restaurants!1 / 26
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Terrace
    • DVD Player
    • Washer
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 February 2018
    Had a great surprise birthday weekend in Key West. The house was fantastic! Very clean and bigger than the pictures make it seem. Loved the heated pool, and close walk to Duval...
    Reviewed 23 January 2017
    3 levels of beautifully decorated accommodations! Walking distance to famous Duval St, bars, restaurants and shopping. Loved it!
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    About this property
    A Key Escape Escape to the Florida Keys for a relaxing vacation in this three-bedroom, two-and-a-half bath home for eight (six comfortably) with a private pool and walking distance to the beach and Duval Street. And your favorite canine friend is also welcome for a small nightly fee. This rental...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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