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Florida Keys Pet Friendly Rentals

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    Travelers to Florida Keys are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    458 Matching Rentals in Florida KeysView all 1,543 rentals
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    Tropical Escape1 / 26
    (85)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 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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    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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    FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 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 6. The boat ramp is 300 yards away and plenty...
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    Marathon Shores, Marathon 33050
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Blue Bungalow1 / 16
    (16)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Wi-Fi
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    My five year old son and I stayed here over the Thanksgiving holiday and had a great trip. We also had our two dogs. The bungalow is tiny (I would not recommend it for more...
    Reviewed September 3, 2018
    Such a perfect and quaint little bungalow to hide away from the hum drum of every day. The owners are so kind and attentive to every detail. Happily tucked away from the hustle...
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    About this property
    Come enjoy the Florida Keys! Many local companies offer opportunities to get out on the water. Go diving or snorkeling. Rent a fishing charter. Rent a kayak or stand up paddle board. We are close to the Everglades where you can birdwatch or see an alligator. Take a day trip to the beaches down...
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    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Conch Key Villas Unit 1, Quiet, Clean with Awesome VIews in Paradise1 / 19
    (13)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
    • Washer
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 31, 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...
    Reviewed March 4, 2018
    I was so lucky to stay two nights at the Conch Key Villas during my bicycle touring trip from Virginia to Florida. I can’t think of a more perfect place to end my trip! The view...
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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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    Conch Key, Florida Keys 33050
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    WOW – waterfront, boat lift, private heated pool, walk to beach and shops!1 / 27
    (1)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 April 25, 2018
    The location is amazing! This duplex is very clean, stocked with anything you would need to cook, play at the pool or go to the beach. We enjoyed the screened in porch and best...
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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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    Marathon, Florida Keys 33050
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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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    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    75130 Overseas Highway1 / 19
    (5)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 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...
    Reviewed June 20, 2016
    This two bedroom home was the perfect getaway for my husband and me. The cute sea-theme décor added to the cozy ambience. The living room/kitchen are flanked with a queen...
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Duck Key Paradise1 / 30
    (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. Minimum stay is flexible. 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...
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    Duck Key, Florida Keys 33050
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Tropical Cottage with Sandy Beach1 / 12
    (51)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Grill
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 18, 2018
    For us, the dock was worth the stay! We enjoyed watching the sunset every afternoon on the dock! The kayaking was fun, awesome and enjoyable, (my new favorite sport). A must...
    Reviewed November 27, 2017
    This cottage was everything we were looking for and expected! So relaxing to walk too the dock and watch the stunning Keys sunsets. We loved the decor of the cottage, too! Lots...
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    About this property
    Cozy cottage with sandy beach located in Key Largo on an acre of tropical waterfront. The children will enjoy playing on the beach with toys provided. Or fish from the 100ft dock with fishing equipment provided. Bring a boat and have FREE dockage. Lounge in the hammock under the palm trees and...
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    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Yard
    • 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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 31
    (5)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Ocean Views
    • Patio
    • Private Outdoor Pool (Heated)
    • Waterfront
    • 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
    ***7 day minimum rental - notwithstanding anything in the rates page the MINIMUM rental is 7 days ****This custom built 5 bedroom house has been immaculately taken care of and has a proper size elevator and is fully wheel chair accessible. Enjoy your stay in Sereni-key looking out to an endless...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 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
    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    New 4 bedroom,4bath in Beautiful Key Colony Beach1 / 21
    (5)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 14, 2017
    The house was everything it was advertised to be, very clean and comfortable. Key Colony is a beautiful place to stay and Toni is one of the easiest home owners I have ever had...
    Reviewed March 26, 2017
    Location and home layout was great, however rental needs some TLC: mattresses were old or cheap - very uncomfortable, pool was dirty (pool on other side of duplex was clean to...
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    About this property
    New 4 bedroom, 4 Bath duplex. This beautiful new home has a private pool, a dock- 2 10 by 30 decks on the channel. The dock is 37 1/2 ft. There are 2 refrigerators, bait freezer, fish cleaning table, 2 bicycles. All bedrooms have flatscreen TV's. The family room also has a queen sofa bed. 3 of the...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Luxurious 3bd/3bth Villa - Your Keys Escape1 / 30
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 25, 2018
    For months I had been trying to figure out how my family & I could take a vacation together with kids & grandkids and this house in the Keys was perfect! We all had an...
    Reviewed July 27, 2016
    I stayed in this condo for a week with my 3 children (ages 12, 19, and 20) and a friend and her child (age 20). The condo was located near all that we wanted to explore in...
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    About this property
    Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2,000 square feet on 2 levels with under cover parking. It is located in the...
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    Location Information
    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    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
    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
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    Dolphin Oasis 4bdr/4bth  Pool/hot tub 115' dockage1 / 35
    (22)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 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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    Marathon, Florida Keys 33050
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH1 / 61
    (8)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 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...
    Reviewed August 31, 2017
    Awesome setup. Beautifully decorated, fully equipped, close enough to walk to just about everywhere you want to be Although I would recommend a bike, cart , or moped.
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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
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    Islamorada Tropical Canalfront Paradise1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Parking
    • 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise n Summerland Key Cove1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 26, 2016
    Whatever I'd hoped for, this vacation home has without question, surpassed any and all expectations! Excellent location; in a quiet and beautiful strip. Loved relaxing on the...
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    About this property
    Amazing canal front 3 bed 2 bath open concept house located in prestigious community of Summerland Key Cove. It is the first canal from open water and one of just a few flow-through canals providing excellent water quality. The canal is deep and wide. Expect to see lobsters, crabs and other sea...
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    Location Information
    Summerland Key, Lower Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    New Listing Family Friendly1 / 32
    (7)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 August 12, 2018
    Wow! Great space! 3 bedroom 3 bath was enough room for everyone. Big tub in one of the king bedrooms and full kitchen with pots pans and extras. Nice back porch with a grill...
    Reviewed April 9, 2018
    What a nice stay! Roy’s communication as host was fantastic. Definitely appreciated the extra effort made. For example, we had ordered cribs for delivery since we were traveling...
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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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    **Winter Promo**  Amazing views from this Oceanside Home near Pennekamp, dining1 / 25
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Parking
    • Grill
    • Patio
    • Air Conditioning
    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
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Location Information
    Tavernier, Key Largo 33070
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
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    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    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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    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Oceanfront duplex with beautiful beach and dock for boat access! Dogs OK!1 / 37
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 10, 2016
    We had our 2 children with us on this trip. (5years, and 3 years.) The beach was beautiful and the kids had a great time swimming and fishing. The house was perfect. We can not...
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    About this property
    Discover the very best of the Florida Keys in this charming dog-friendly (for an additional fee) rental with a dock and beach! The unique home offers the makings of a romantic getaway or intimate retreat with friends. The rental is three miles from town and a few hundred feet from the Long Key...
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    Location Information
    Long Key, Florida Keys 33001
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    Deam home in they keys is one of the very few legal weekly rentals in Islamorada. It is a 4000 square foot home on water with heated Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Marathon, Florida Keys 33050
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Incredible Luxury Home with Waterfront!! Paradise1 / 17
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    • Hot Tub
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    • Central Heating
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    • Waterfront
    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
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PARADISE LIVING: Enjoy the view from our large porch overlooking a deep, wide, crystal blue clear canal with quick boating access to the Atlantic Ocean. Looe Key Coral Reef is a short distance away by boat for some of the best diving and fishing the keys has to offer. If you prefer to stay home,...
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    Location Information
    Summerland Key, Lower Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fabulous 6 Bedrooms /4 Bathrooms Tropical Waterfront Pool Home!1 / 15
    (1)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 (Unheated)
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    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 Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. Our beautiful home is Great...
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    Location Information
    Islamorada, Florida Keys 33070
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a spacious, canal water front, open layout, 2 bedrooms, 2 baths, ground level home that can accommodate up to 6 guests with plenty of room to spare. It is a short walk from multiple restaurants, bars, waterfront parks, and the Cabana Club. We are located on the ocean side, however you will...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Great Fishing Right Off the Dock!!1 / 22
    (6)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 1, 2017
    Having the Florida Keys on my bucket list can now get a BIG check mark! I took my family and both small dogs (which go everywhere with us) to the keys and can say that renting...
    Reviewed October 20, 2016
    Here's the scoop!... The fishing off the dock truly is great and just the relaxing atmosphere and access to the channel and ocean are worth it alone. Make sure you have fishing...
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    About this property
    This is one of the best vacation spots in the keys.It's a lovely 4 bedroom/3 bath Duplex on 3rd St. The sleeping arrangement include 1 King, 2 Queens, 2 twins plus sleeper sofa. The living room is spacious. Enjoy fishing on the large 56 foot dock The ocean is just seconds away by boat.There is a...
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    Key Colony Beach, Florida Keys 33051
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Luxury Open Water Vacation Home1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 20, 2016
    We just returned from a fabulous vacation at this house. It was so relaxing, the views were awesome. We saw so many kinds of birds. It is absolutely a perfect place to enjoy...
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    About this property
    OPEN WATER PRIVATE ESTATE 3 Bedroom 2 Bath, with a large Pool. Sleeps 4 to 6 $250 - $268 Per Night Minimum Stay 1 Nights Enjoy your piece of paradise and the warm tropical air of the Florida Keys in your own 2600 square foot, private open water estate in a quiet relaxing neighborhood....
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    Location Information
    Big Pine Key, Florida Keys 33043
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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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    • Cable/satellite TV
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    • Waterfront
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Heated)
    • 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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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    'Gulfside Grouper', Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK1 / 43
    (6)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 3 weeks ago
    Beautiful house on Marathon Key. It was our own private resort. The one level house has easy access to all the amenities it has to offer. We enjoyed the unique beautiful...
    Reviewed October 13, 2018
    Grouper has all the amenities you could need in a vacation rental. Large open concept home, screen porch, fire pit, patio chess/checkers, corn hole. Poolside tiki hut. The beach...
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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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely waterfront home is located on mile marker 29, on the ocean side of Big Pine Key. Just 30 minutes from Key West, this hidden gem offers quiet relaxation, while still close enough to enjoy the party atmosphere of Key West! Dock your boat out back, sip on your favorite drink and grill your...
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    Location Information
    Big Pine Key, Florida Keys 33043
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    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
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    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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful million dollar plus home is located at 220 15 Circle in a very exclusive area of Key Colony Beach. It is available Sat to Sat. This fantastic community is one of the most unique places in the world. The gem clear waters are the home of an almost endless variety of fish and marine...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Welcome to our newly renovated, little slice...
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    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elegance and luxury living await you at this private, waterfront home in Key Largo, on mile marker 99. Come and relax at our beautiful home, located in the Sport Fishing Capital of the World. Just minutes from John Pennekamp Park as well as many dining, shopping and grocery options....
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    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Housekeeping Included
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    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
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations since I am not a real estate salesman or property manager allow me let the photos speak for themselves. My oversized two bedroom, one bathroom condominium is located on picturesque Southard...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    **Winter Promo**  Ocean Front Keys Home with Private Beach - Great for Kite Surf1 / 25
    (2)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 6, 2016
    Had a wonderful time beach just out front and did a lot "beaching". Close to a nice supermarket and rental places. Will definitely be back! Thanks for a great get away!
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Beautiful four bedroom, Ocean Front home with...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
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    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to paradise on mile marker 90, minutes from the Ocean or Bay. Relax 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...
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    Location Information
    Tavernier, Key Largo 33070
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    • DVD Player
    • Cable/satellite TV
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a spacious, open floor plan, Three bedrooms, Two Bathrooms, 6 people accomodation, brightly painted colors, beautifully furnished. Relax in the upper covered porch or down below to the open and spacious patio leading to the pool. Outdoor Tiki shower hut. The grounds are landscaped with an...
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    Location Information
    Summerland Key, Lower Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    • Cable/satellite TV
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us for discounts *** Infinite ocean views from the large windows at this modern and luxurious oceanfront condo at mile marker 87. Accommodation - Sleeps 4 Master Bedroom: - King Size Bed - Night Stands - Reading Lamps - Dresser with Drawers...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    • Wi-Fi
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    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful four bedroom, waterfront home with a private dock & pool in sunny Key Largo (MM 104). Welcome to your own Keys oasis! Kick back like a local and relax in your own Keys home. This spit level house is located in Key Largo; the Sport Fishing Capital of the World. It is a private home with...
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    Location Information
    Tavernier, Key Largo 33037
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Waterfront
    • Cable/satellite TV
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    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you have your sights set on the ideal spot to spend your next tropical getaway, then jump on the chance to book your stay at this dog-friendly, oceanfront Islamorada home on a one-acre lot. Boasting a private stretch of white sand beach, a private pool, hot tub, and water toys like kayaks and...
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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