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Pet Friendly Holiday Rentals in Florida Keys

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    Travellers to Florida Keys are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    339 Matching Rentals in Florida KeysView all 1,347 rentals
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    Comfortable Clean HouseBoat in an amazing location1 / 32
    (4)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    LA DOLCE VITA, OLD TOWN KEY WEST!!  STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH1 / 27
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Luxurious 3bd/3bth Villa - Your Keys Escape1 / 30
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Summer Blow Out! $300 off. Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Satellite TV
    • DVD Player
    • Ocean Views
    • Parking
    • Patio
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2017
    Great place to stay. Wonderful amenities! Would highly recommend. Location is great for beach, Mallory square and Duval Street.
    Reviewed 18 June 2017
    We had such an awesome time in Key West, and it all started with our accommodations at Tiki Beach Too! The Shipyard complex where the condo is located is in the perfect place...
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool<BR><BR>Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Keys Cove Getaway 2BR 2BT1 / 10
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Grill
    • Private Garden
    • Ocean Views
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 July 2017
    What can I say? I will definitely rent this place again. It's located in a convenient place and most of all it's quiet and clean. The owner is a nice honest lady too.
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    About this property
    Looking to vacation in the beautiful keys? Our spaceous 950sq ft. Home is conveniently located close to many of the things the keys has to offer! After enjoying a fun filled, sun soaked day come home kick back and relax at our little piece of paradise. Our beautifully decorated beach theamed home...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4BR Waterfront Retreat-Tiki-Jacuzzi-Dock1 / 12
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    House was great for us unfortunately Hurricane Irma caused a mandatory evacuation on Wednesday morning. Not sure if there is anything left of the house. Not sure the Trp Advisor...
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    About this property
    This is a fantastic community and 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 life. It has a private 60-foot dock with deep water that will accommodate any size boat. In minutes you can be fishing in either the...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    **Ready After Irma** Luxurious Key Largo Family Home with Pool & Large Dock1 / 24
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2016
    Loved this house! It was beautifully decorated, spacious, comfortable and immaculate. The kitchen was great for eating meals in, but there were also plenty of really fun...
    Reviewed 27 October 2015
    We always go down to the Keys as a family in the summers and spend about a month there. In all my years of spending my summers down in the Keys, I do not think I have ever...
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    About this property
    This property has been inspected after hurricane Irma, is in good standing and is gladly accepting reservations at this time. We look forward to having you stay with us! *** Owner is highly motivated to rent! Contact us for discounts *** This luxurious waterfront home is located on mile marker 106,...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Beautiful Beachfront Home w/Pool/Spa/45' Dock1 / 41
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Terrace
    • Air Conditioning
    • Grill
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Secure Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2017
    When we arrived we were immediately impressed with the house, the rooms are beautiful, beds are comfortable, kitchen is fully stocked with anything you would need for cooking...
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    About this property
    Beautiful Beachfront home located directly across the street from famous Sombrero Beach. Sombrero Beach is surely one of the stand-out beaches in the Florida Keys. This pet friendly beach has something for everyone. Kayaks, boating, fishing & biking all easily available for great fun in the sun....
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    TARPON FLATS INN AND MARINA1 / 6
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 February 2017
    My husband and I reserved a suite on the ground floor which was both convenient and lovely. The Inn was a quiet oasis minutes from Pennekamp state park and was just what we were...
    Reviewed 5 June 2015
    one of the nicest place&staff i have ever rented hope to go back soon and visit gilda & crew DANNY&SHIRLEY TRY IT YOU WILL LIKE IT DANNY
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    About this property
    Escape to Key Largo's ultimate weekend or vacation getaway ~ the best Inn in the Florida Keys. Located directly on the Atlantic Ocean, in unspoiled Largo Sound. Offering the best access to the finest of Florida Keys charter fishing, Everglades's excursions, Eco-tours, snorkeling and scuba diving....
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    75130 Overseas Highway1 / 18
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2017
    We stayed here for a few days and it was amazing. The house is warm and cozy and has all the details you need when away from home. The beachfront is wonderful and can go...
    Reviewed 21 June 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • Waterfront
    • Grill
    • Washer
    • Central Heating
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Ocean view, on a canal, three lots from open water in Venture Out Resort; a safe, gated community. Park your boat or kayak right outside your front door on the canal, or just relax and enjoy your mosaic picnic table and 4 patio chairs, and Weber charcoal BBQ. Only 7 steps up or down to...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Secure Parking
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront unit with a 23 ft Center Console boat. The boat is docked outside your unit for your exclusive use during your stay. We are conveniently located for either bayside or ocean access. There is a dive shop and bait shop in the complex. The unit is 2 bedrooms and has wifi, cable tv,...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Vacation Pool Home 2 Bedroom & 2 Baths Sleeps 8 w/ 60 Feet of Dockage We survived Hurricane Irma and these pictures were taken after the storm. Discover the Ease of Booking a FL Keys Vacation...Welcome to Sachs' Sea Shack…Bayside Deep Waterfront Pool Vacation Home with 60 feet of...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    'SANDY BEACH' Key Largo,Fl. Luxury Vacation Rental1 / 31
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2014
    This place is truly amazing! The beach is clean and the good sand extends out into the water. The amenities are endless in the house. Kids loved the pool as it gave them a...
    Reviewed 15 March 2014
    My family of 7 including 2 babies just had a wonderful week at Sandy Beach. The house is perfect for a groupwith large quiet bedrooms. The outdoor kitchen and beautiful private...
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    About this property
    Welcome to 'SANDY BEACH' in Key Largo, Fl. Enjoy amazing sunsets from your own private white sandy beach and swaying palm trees that leads you into the warm ocean blue waters of the Florida Bay. This gated 1 acre 3/3 pool home has been updated and beautifully decorated. It can sleep 8 to 10...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Mango Hideaway-King Suite just steps off Duval St1 / 18
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Patio
    • Grill
    • Private Garden
    • Wi-Fi
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    The Mango Hideaway is a nice spot in the middle of Old Town. Walking distance to everything. Private patio and entry off of the side street are a plus. Great location and a...
    Reviewed 4 March 2017
    We had a great time in Key West staying in the Mango Hideaway!Very private and comfortable yet only a minutes walk to Duval street.Also centrally located in old town so seeing...
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    About this property
    Mango Hideaway is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local as...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Private & Peaceful Oceanview Estate Away From All1 / 68
    (48)Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
    • Patio
    • Hot Tub
    • Washer
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 January 2017
    This house was perfect for our large family to stay. We used the whole property and Kazi was great to work with. We had perfect weather and we had a great time in the pool...
    Reviewed 15 January 2017
    Kris and Adam both of our fabulous host were fantastic! When we arrived Kris was there to welcome us and made our check-in easy, answered any questions and any issues right away...
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    About this property
    NOTE: To send us your reservation inquiry, visit the White Ibis Inn site and fill out the “Contact Us” page for the fastest response. You can also view photos, weekly specials, rooms & rates on our site. White Ibis Inn away from the hustle of Key West activities, but close enough to the excitement...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Grill
    • Balcony
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    YOUR PRIVATE GETAWAY IN KEY WEST, FLORIDA.  This beautifully historic 2 bedroom 2 bath home is conveniently located in Old Town Key West, FL. Just a short walk from everything you could dream of, for your island vacation. Just 5 blocks from the famous Duval Street. Two blocks from the seaport,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elegant, Two Bedroom Condo Close to the Ocean1 / 14
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Satellite TV
    • Hot Tub
    • Balcony
    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
    Reviewed 15 July 2016
    This condo was amazing. The service provided was excellent. I loved the location and it was just what i was looking for. Knowing we had a great place to stay made the trip even...
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    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mockingbird Pointe - Waterfront Tropical Escape1 / 44
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Washer
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    We loved our stay at Mockingbird Pointe! The grounds are absolutely beautiful with lush, tropical landscaping. With the house at the end of the road and on the wider part of the...
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    About this property
    Mockingbird Pointe is a quiet secluded 1/2 acre tropical waterfront paradise in the heart of the Florida Keys with a brand new private 16' x 32' in ground cement swimming pool with splash deck. This two bedroom , two bath home is newly remodeled, furnished and completely renovated with new...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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)
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elegant Beach Home With Dockage1 / 24
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 April 2017
    They home was great. It had everything you could ask for. The people that we met at the home very friendly. We had a great stay and I will come again. I high recommend this home.
    Reviewed 19 September 2016
    We stayed here Aug 8-12 with my parents, brother and sister. Not only was the home perfect, but the location was great with several food places in walking distance. We walked...
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    About this property
    Elegant home with many unique, architectural features, located on a family-owned waterfront piece of property, with 3 other rental cottages, sandy beach, and small marina.<BR><BR>This lovely house, "Tropicasa", has everything needed for a large group - full kitchen with granite countertops,...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Terrace
    • Patio
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This neat oceanfront home is located directly on the Atlantic and is available Sat to Sat. This ideal location is near MM 51.7 at the end of 84th street Oceanside Marathon 33050. This Ocean front home is completely tiled and has central air. The 3 bedrooms have TVs with a 2 full bathroom. There is...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Family Retreat Oceanfront Home with Pool1 / 18
    (13)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Hot Tub
    • Grill
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2016
    The house is designed perfectly for a mixed aged family group. Lots of separate areas for different activities and also a large area for the whole group to celebrate together...
    Reviewed 19 June 2015
    12 of our family came down from NC & VA to celebrate a college graduation and fulfill some bucket list items. It was a classic road trip and the very best vacation imaginable...
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    About this property
    Oceanfront 6 bed/4 bath home with panoramic ocean view on Cudjoe Key. Sleeps 12+. Beach, Hot Tub, Floating Dock, Heated Pool, Kayaks and 540 square foot screened in porch overlooking the Atlantic ocean. This house has been very popular with large groups. Floating dock is great to fish and swim...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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    FLORIDA KEYS OASIS - The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 32
    (4)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Washer
    • Air Conditioning
    • Ocean Views
    • Patio
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 July 2017
    The property manager was super helpful and walked us through the entire house showing us all the nooks and crannies. I must say I've never had someone take close to 45-an hr to...
    Reviewed 13 February 2017
    On our recent family trip to the keys, we were lucky enough to find this amazing home. We stayed for one week and wish we had stayed a month!The house is 6 stars and the hosts...
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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
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    Dolphin Oasis 4bdr/4bth  Pool/hot tub 115' dockage1 / 35
    (14)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 August 2017
    We couldn't be more pleased with the location, the home, the amenities, or any aspect of this vacation getaway! We have stayed in many different vacation homes in the Key's and...
    Reviewed 8 June 2017
    This property is spectacular!! It doesn't feel like a "rental"...it's like visiting someone with an amazing water-oriented home. The owner (Craig) is personally...
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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
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    Dog-friendly half-duplex w/ 30-ft dock - access to shared pool & beach1 / 30
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Satellite TV
    • Waterfront
    • Washer
    • Air Conditioning
    • Grill
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2017
    GREAT PLACE! Boat parking out back door. Relaxation at its best. Bicycle paths through community. Beach, pool, bars. Fully furnished kitchen, beach and bath towels, clean linens...
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    About this property
    For a luxurious paradise retreat, look no further than this dog-friendly home in Key Colony Beach. With a 30-foot dock and access to The Cabana Club with a shared pool, beach, and more, it's the ultimate getaway! Located in Key Colony Beach, this duplex home is on a canal that leads out to the...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Waterfront
    • Central Heating
    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Welcome Aboard the 'Manatee' as we say here at Mangrove Marina, located in the northern end of Islamorada in Tavernier at Mile Marker 91.7 on the Bay side in a protected tranquil oasis cove of the beautiful Florida Keys. Our houseboats are a boat lovers dream with all the comforts of home,...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Neat, clean and perfect for a family vacation. This 2 bedroom, 2 bathroom home sits on a wide, deepwater canal Comfortable beds and furniture. Plenty of parking and room for a boat trailer onsite Optional access to a pool at the Glunz Ocean beach club $12 per person per day Outside Covered...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Best Value 2 BR Stilted 1/2 duplex on Canal1 / 11
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sorry, Not available Dec 1 2016 to April 3, 2017. Modern and attractive 2 BEDROOM, 2 BATH, CANAL-FRONT, Stilted Half Duplex Features : * Comfortable and cozy furniture and bedding + new bathroom * Centrally located in Marathon and 7 minutes to Sombrero Beach * 37 feet of deepwater dockage and...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Waterfront
    • Washer
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    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright bayfront half-duplex offers water views, central A/C, and access to the Cabana Club where you'll find a shared pool and a private beach! You can even bring your dog for a small additional nightly fee. Located just off East Ocean Drive, guests may enjoy the private beach and pool at the...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tropical Escape1 / 26
    (84)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    This place is just perfect! Nice and clean, and check in was a breeze! But what I really loved about it is the location! You are in Key West, but you are far enough away from...
    Reviewed 8 July 2017
    Owners were great and very accommodating. The condo is beautiful. Has everything you need. Pool was great to use. We would rent again when we come to key West. We had a great...
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    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    • Waterfront
    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This dog-friendly home has everything you need for a trip to the Florida Keys: a private 35-foot dock space, Cabana Club membership, and classic home comforts! This canal front home for eight offers swimming, fishing, and more from your private dock! If you're in the mood for more traditional...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In search of tropical views and blissful privacy in the Florida Keys? This beautiful four-bedroom Marathon home provides guests with their very own beach, swimming pool, and dock on serene Florida Bay. And two dogs are welcome, too, for a small nightly fee! Scenically situated on Grassy Key Bay,...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Washer
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    • Satellite TV
    • Waterfront
    • Patio
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're headed to Florida for your next vacation, come stay in this comfortable duplex, featuring gorgeous bay views, a 30-foot dock, and Cabana Club passes for shared pool and private beach access. Bring your group of up to eight (and the family dog, too!), and revel in the versatility of this...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Catamaran CALYPSO with Summerallthetime Sailing Co1 / 31
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Secure Parking
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    • Ocean Views
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2017
    We had the pleasure to sail around the Florida Keys on the Calypso last month. The boat was great and very well kept. Beds were comfortable and cabins felt clean and polished...
    Reviewed 28 March 2017
    Capt John took our family of 4 on an ultimate Spring Break Keys journey!The sailboat is well equipped and very clean and modern. We had plenty of room to rest and play on...
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    About this property
    The Beautiful 42' Catamaran Calypso is a spacious Luxury Boat with all the latest Amenities. With 3 Cabins available... it sleeps 6 people comfortably. Each cabin has its own bathroom with all new faucets and electric flush toilets. Aboard Calypso you will find several places to lounge, sit back,...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Dog-friendly family home on deepwater canal, close to beaches!1 / 47
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Patio
    • Internet Access
    • Satellite TV
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    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearby beach access, a private dock, and tropical views are a few great amenities at this three-bedroom, three-bathroom, pet-friendly Marathon vacation rental with space for up to eight guests! Located in a quiet neighborhood on a deepwater canal, this home is within five miles of Sombrero Beach...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Luxurious Condo-Exclusive Bay Harbour w/Boat Slip & Marina, Pool, Tennis courts1 / 15
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2015
    Great property! Very beautifully decorated. I loved the view, really enjoyed my stay! I look forward to staying there again soon!
    Reviewed 20 January 2015
    This condo is beautifully decorated and chock full of everything you need to make your stay just perfect. The condo and the complex are extremely well maintained and have the...
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    About this property
    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This lovely property is part of a gated,...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Waterfront
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    • 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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is the Perfect getaway for large groups!  You can rent from 1 to 4 homes depending on the size of your group. The Pelican and Egret homes will offer you 2 homes, 5 bedrooms, and one pool.  The Pelican is a 3 bedroom 2 bath ocean front pool home which will sleep up to 8 people.  (Sofa...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Washer
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    • Hot Tub
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your Florida Keys retreat just got even better! With its dog-friendly attitude, private heated pool and hot tub, and plenty of space, you'll feel like you're in sunshiny heaven. Situated on the western edge of the island, you'll be close to the Key Colony Beach Golf Course, fun parks, and ocean...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For a fun-filled fishing getaway and other high seas adventures, this two-bedroom Marathon condo can't be beat! Drive a boat out from its 17-foot dock, store your fresh catch in its bait freezer, and spend glorious days under the sun with your group of up to five guests and two dogs. Residing on a...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your family, your dog, and your tackle box to this Florida Key vacation rental. Located in Marathon on Vaca Key, this dockside beach house is the perfect place to unwind. If you’ve ever wanted to take that epic fishing trip, this bayside home is an ideal basecamp as it offers 35 feet of dock...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Savor the beauty of the Florida Keys in this charming waterfront, dog-friendly, Key Colony Beach home complete with a screened-in porch, fish cleaning station, and 60-foot dock for parking your boat after a day on the water. It also includes passes to a local private beach and access to the Cabana...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Go on a Key Colony Beach retreat at this updated dog-friendly home. Enjoy a 30-foot dock, and exclusive access to The Cabana Club private beach, swimming pool, and restaurant. Located right on the water in the popular vacation spot of Key Colony Beach, this duplex home is minutes away from The...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With a 60-foot dock right on the canal and access to the nearby Cabana Club's shared pools and private beach, this dog-friendly bungalow is perfect for your next getaway to sunny Florida! Located in Key Colony Beach, this home for six is located on a canal, with swimming and fishing available in...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Between the private hot tub and a great location, this dog-friendly Marathon home is perfect for your next vacation in the Florida Keys! Your new home away from home for six is just a short distance from plenty of delicious restaurants, with a gorgeous, recently landscaped backyard. Don't forget...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When you're ready for a paradise escape, this dog-friendly Key Colony Beach home features a swimming pool, a 75-foot dock, and plenty of room for relaxing and entertaining. This home is located right on the water in Key Colony Beach in the popular Florida Keys - a tropical destination for sport...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your family, friends, and canine companions along for the ride with this dockside vacation home in Key Colony Beach! This home for six lets you take in some Florida sunshine right by the canals in the backyard. If you get tired of fishing, kayaking, and swimming by the dock, you have a...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Go boating, fishing, and snorkeling with ease at this Marathon home, a dog-friendly Florida Keys escape with a 40-foot private dock, a provided kayak, and a lovely bayfront deck with gorgeous views. This waterfront house sits on an ocean inlet on Knights Key, a location made famous by the TV show...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright and spacious Key Colony Beach home is the perfect oceanside getaway! Complete with 35 feet of dock, and access the local Cabana Club, you're sure to relax here. One dog companion (under 30 pounds) is also welcome aboard for an additional nightly fee. A stay in this dreamy abode grants...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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