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Florida Keys Pet Friendly Vacation Rentals

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    Travellers to Florida Keys are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    467 Matching Rentals in Florida KeysView all 1,482 rentals
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    SPECIAL FALL RATES, INCL. LABOR DAY - BOOK NOW!1 / 27
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Blue Bungalow1 / 14
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    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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    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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    Amenities & Details
    • DVD Player
    • Parking
    • Terrace
    • Cable/satellite TV
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 12, 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 February 28, 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
    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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    • Internet Access
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Waterfront
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 21, 2017
    Perfect stay for all of us. The kitchen was perfect for our meals. We all slept very comfortable and we enjoyed the decorating that has been done. We enjoyed all the different...
    Reviewed January 11, 2017
    Very cool and unique lodging. Not luxury but very nice and clean. Great communication with host. Very friendly. Great decks/outdoor spaces on boat.
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    About this property
    The houseboat's 11-foot ceilings with exposed beams, ceiling fans and air conditioning provide a feeling of spaciousness and comfort. A full size refrigerator, sink, microwave and cook-top stove makes cooking easy. It has a comfortably sized bathroom with a full size shower. The Master Bedroom has...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    75130 Overseas Highway1 / 19
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 22, 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 August 13, 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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    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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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    • Washer
    • Patio
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 17, 2018
    This rental was simply amazing. The house was emaculant, cleaner than anywhere we have ever stayed. Every detail was laid out for us. The beds were comfortable, the house was...
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    About this property
    Discover the Ease of Booking a FL Keys Vacation...Welcome to Sachs' Sea Shack…Bayside Deep Waterfront Pool Vacation Home with 60 feet of Dockage in Marathon, FL, the heart of the Florida Keys. A newly renovated 2 bedroom & 2 bath home that sleeps 8. The boat ramp is 300 yards away and plenty...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • 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 August 27, 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 March 22, 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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    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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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 August 6, 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 August 28, 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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    Location Information
    Marathon, Florida Keys 33050
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    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 January 20, 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 March 23, 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, non-refundable pet fee...
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    Location Information
    Key Largo, Florida Keys 33037
    Condo/Apartment - 1 Bedroom, 1 Bathroom, 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 January 27, 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 August 18, 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
    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 July 1, 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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    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 January 16, 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 November 9, 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 with Quintessential Island Living1 / 44
    (5)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Patio
    • Parking
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 30, 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 July 12, 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 11
    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 May 1, 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 May 23, 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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    Location Information
    Key Largo, Florida Keys 33037
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Duck Key Paradise1 / 34
    (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 October 11, 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 September 21, 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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    Location Information
    Duck Key, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Waterfront Home w/EZ Ocean Access*Boat Slip*Roof Top Deck*Hot Tub*28 nt min1 / 44
    (2)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Hot Tub
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 22, 2015
    In our first trip to the Florida Keys, we stayed at this home. It is a very nice home, located close to everything. Great kitchen - it was nice to be able to comfortably cook...
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    About this property
    Fabulous, like-new, waterfront vacation home located in the Heart of Key Largo! You'll love the convenient location, the boat slip, and the peek-a-boo ocean view from the fabulous roof top deck! This stunning vacation home is ideal for vacationers planning to enjoy either land or sea activities or...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    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 June 5, 2019
    clean and well furnished. Very responsive owner. Close to downtown Key West.We would rent this place again.
    Reviewed January 23, 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
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    A quiet spot in paradise close to fishing with dockage included (#4)1 / 13
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 28, 2018
    Best view in the Keys! Extremely clean and spacious! Owners very attentive and friendly! Had the most relaxing holiday weekend! Recommend without a doubt and will be back!
    Reviewed May 17, 2018
    Awesome spot, Owners gracious and very helpful with local attractions.Would love to book for next year.
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    About this property
    This second floor Studio has a King-size bed as well as a pull out futon in the living room. We can accommodate 2 adults and 1 child under12. This Villa is situated facing due West right on the water and has a combined living and dining area. The Villa has a kitchen equipped with microwave, coffee...
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    Location Information
    Conch Key, Florida Keys 33050
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    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 June 16, 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 July 16, 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
    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 September 29, 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 February 27, 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
    SPECTACULAR Waterfront Key Colony Beach Home w/Heated Pool & Dock1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 22, 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
    Dolphin Oasis 4bdr/4bth  Pool/hot tub 115' dockage1 / 36
    (22)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Ocean Views
    • Waterfront
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 3, 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...
    Reviewed April 7, 2018
    Our family has been coming to Marathon for the last 4 years. The Dolphin Oasis house fully exceeded our expectations. The attention to details on this property are second to...
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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
    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)
    • Grill
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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
    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 November 9, 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
    Amazing views from this Oceanside Home on the Tavernier Creek Waterway; New Dock1 / 24
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 10, 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 March 25, 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
    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 September 19, 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 March 28, 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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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    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
    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 September 29, 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 June 20, 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
    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
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    • Hot Tub
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 5, 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 December 5, 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
    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
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 15, 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 March 7, 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
    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
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    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 5, 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
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    • DVD Player
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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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    Location Information
    Sugarloaf Key, Florida Keys 33042
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Villa Sombrero, Marathon1 / 48
    (1)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Washer
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    • Cable/satellite TV
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    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 1, 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
    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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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    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 July 30, 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 April 12, 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
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • 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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    Marathon Shores, Marathon 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    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
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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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    • Cable/satellite TV
    • Balcony
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    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peaceful and Scenic Keys Home, Newly Remodeled; Centrally Located on Plantation Key, near grocery stores, Old Tavernier Restaurant, Marinas, Founder's Park, and much more! The peaceful, secluded surroundings make this home the Ultimate Keys Getaway! Plenty of spacious accommodation on patios for...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise, on mile marker 106 on the bayside! Come and relax at our newly remodeled mobile home, located in the Sport Fishing Capital of the World! Minutes to Adams Cut. Near from John Pennekamp Park as well as many dining, shopping and grocery options. ** PETS WELCOME ONLY WITH OWNER...
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    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the comfort and convenience this beautiful 2-story Key Largo home with your very own private pool in the spacious backyard. Bring your boat and keep it the Buzzard's Roost marina near by at NO additional cost! Just minutes of world-class fishing, snorkeling, diving and much more! Whether...
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    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    'Gulfside Grouper', Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK1 / 43
    (8)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 3, 2019
    Don't think twice about about this amazing place. Our family has been vacationing in the Keys for years and this house was our favorite by far. Aside from the perfect location...
    Reviewed July 8, 2019
    My family and I have stayed in marathon for many many years, I have to say this was the best lay out for family and fishing in the keys! Absolutely gorgeous home with more than...
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    About this property
    Brand New Vacation Rental completely remodeled in 2018 and Available for rental in November 2018 Ground Floor Home 'NO STAIRS' we love that the house located on a Quiet street 4 houses in from the gorgeous Gulf of Mexico and minutes from the Ocean Side and Sombrero Reef via VACA cut or under 7...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    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
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    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 26, 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 July 31, 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
    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 February 28, 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 January 23, 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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    Stock Island, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2 BD/2 BA stilted, single family home offers great potential for summer fun! 2 kayaks included! Big Porches to enjoy the ocean views with an East exposure for morning coffee. This home sits canal front and has an open water view, includes a boat ramp and pool.  Pool has outdoor bar and...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • DVD Player
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    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7 night minimum, NO EXCEPTIONS Max Occupancy: 6 (NO MATTER THE AGE) Per the city of Marathon's rule of 2 per bedroom plus 2. NO EXCEPTIONS. Blue Marlin is a newly remodeled single family home!  It features 2 bedrooms and 2 bathrooms. The master bedroom has a king bed with en-suite...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a nice clean and updated place in the Keys? This home will NOT disappoint. Superbly renovated, ground level house. The  kitchen has been updated with stone tile counters. Bathrooms are marble and tile.   Full kitchen with stove and fridge, dishwasher, pots and pans and microwave....
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
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    • Grill
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise!! Come and relax in our Bayside home and enjoy the coastal breeze and rustling palms in your own private oasis. Sure to become your favorite Keys home-away-from-home, this waterfront villa boasts elegance at every level with its spacious layout, modern decor and luxurious...
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    Location Information
    Tavernier, Key Largo 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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