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Florida Keys Oceanfront Vacation Rentals

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    Travellers to Florida Keys are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    69 Matching Rentals in Florida KeysView all 1,479 rentals
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    Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage1 / 39
    (39)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oceanfront 2 Bedroom 2 Bath Condo Key West Florida1 / 17
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Florida Keys Beach Home Pool Fishing Diving1 / 72
    (29)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Children's Pool
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    Everything was perfect. Weather was great, the unit was clean and fully furnished with everything we needed. The other vacationers and full-time residents were friendly and...
    Reviewed 6 May 2016
    This condo was to die for. The decor was fabulous and the location was perfect and close to many restaurants. The sunset from the balcony was breathtaking. The owner was a...
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    About this property
    Beautiful / tropical decorated one bedroom, one bath water front condo in Summer Sea Condominiums located at Mile Marker 88.5 Bayside Islamorada, FL. Bayside means amazing open water views & world famous Florida Keys sunsets from your own private balcony overlooking the Florida Bay. You can also...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    TOP FLOOR - END UNIT - OCEAN VIEWS ALL ROOMS !1 / 56
    (23)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2017
    The condo is wonderful - the beach is on the doorstep and the view from all the windows is amazing! It is a great family-friendly condo with a great pool area, the area is super...
    Reviewed 2 August 2017
    Immaculate and well decorated condo with a helpful and responsive host. I would definitely stay there again
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    About this property
    Freshly updated after Hurricane Irma we are open for business! We received Trip Advisor's 2017 Certificate of Excellence 'Best Condo in the Keys' award! Its all about being tastefully decorated, on the top floor of the best building with the largest end unit with the most windows - twelve. See a...
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    Tavernier, Key Largo 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    ONLY AVAIL: April 10-28 for 6; 2BR/2BA/INCH BEACH/30' Dock; NO CC POOL or pets!1 / 92
    (94)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Ocean Views
    • Washer
    • Waterfront
    • Wi-Fi
    • Housekeeping Included
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2017
    This was the third time we've rented this house and as usual it was great. They updated some of the outdated furniture, which was a nice surprise. I can never say enough nice...
    Reviewed 19 May 2017
    Seriously, if you are looking for a place in the Keys you can stop looking now. I don't know how any place could beat this one. The house has EVERYTHING you could possibly need...
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    About this property
    Welcome to 'KEYS OCEAN DRIVE', the BEST rental LOCATION in KCB!!! 2018: • April 7 -28 available ONLY! We are closing on the sale after 4/28th! • 7 night 'licensing' minimum, flexible check in & check out dates, ASK! We are located ocean side with quick & convenient boating access to gulf side...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Our Kozy Key - Paradise FUN at your door.1 / 55
    (22)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Grill
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2018
    Our Kozy Key is a wonderful place to spend time with friends or family! Great for all ages...from babies to grandparents. The door to the pool and lagoon is literally less than...
    Reviewed 31 August 2017
    We really enjoyed the peace and quiet of the Kozy Key at Kawama Yacht Club. It was out of season and so we practically had the place to ourselves. It's ideally situated for...
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    About this property
    Welcome to the beautiful Florida Keys! We're Greg and Stevie (Stephanie) Bovee from Glenwood Springs, CO. We have a wonderful vacation rental in the Florida Keys that we would love to share with you. Our 2 bedroom 2 story townhouse is located in the tropical resort of Kawama Yacht Club, Key...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Private Heated Pool, New Boat Dock and Ready Enjoyment!1 / 23
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2017
    Spent our week family vacation here. Fresh, clean and adorable cottage. Although on the smaller side the yard is excellent and larger than most with plenty of shade. Access to...
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    About this property
    Come enjoy the Keys Life in the single best location in all of the Florida Keys. 'Miloh's' has been completely renovated in 2016. Dock your boat in the large deep water canal and cool off in your private pool. Enjoy the built-in underwater bar stools in the pool as you enjoy a cold beverage and...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Family vacation rental, kayak, pool, 50” dock1 / 36
    (2)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Patio
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2017
    I was a bit worried because of the other review but I'm glad I took the risk. This home is amazing. It is absolutely beautiful. Being from Miami and having stayed at every run...
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    About this property
    Luxury property Designer decorations in a modern-tropical and very cozy style with a friendly and relaxing We are located 45 minutes from the city of Miami that in turn can enjoy mall and night club, and around has broad line of restaurants, and tourist attractions such as fishing, surfing, diving,...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Children's Pool
    • Washer
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on...
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    Location Information
    Islamorada, Florida Keys 33023
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 / 1 Apartment Key Largo in Pennekamp1 / 88
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Waterfront
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2016
    This was a wonderful place great views close to everything snorkling,kayaks,glass bottom boats. Jesus and Zoe are awesone, I would highly recommend this for a great relaxing...
    Reviewed 24 March 2015
    The apartment with it's location on a canal was more than we expected. Jesus, the owner, was accommodating and gave us great information regarding the area. With the kayaks he...
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    About this property
    Spacious apartment in Quite street, Key Largo Recently remodeled one bedroom apartment centrally located in the Heart of Key Largo. Private, Safe and Quiet residential neighborhood within walking distance to John Pennekamp National Park. Kayak right into the parks beautiful mangrove canals and...
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    Location Information
    Key Largo, Florida Keys 33037
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cottage w/ Free Everglades Kayaking, Snorkeling, and Bay Sailing1 / 35
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2018
    Key Lime Sail Club is a really cool, easy going, old school Keys hide away. You can take sailing lessons or take a cruise on the crewed catamaran for a kayaking trip into the...
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    About this property
    The Hideout Cottage has a full size bed and one single bed, kitchenette with 4 burner electric stove, full-size microwave, small fridge with complete kitchen and dining utensils plus linens and towels are provided. This cottage can sleep 2 adults with 1 child or 2 children if a provided cot is...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    PARKING,2bd/2bth,20yrd TO DUVAL,FREE OLD TOWN SHUTTLE,MAJOR ATTRACTIONS NEARBY1 / 41
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Patio
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2018
    Best part, it is right off of Duval and close to so many things to do. The beach is 5 minute walk and the community pool is an amazing unused gem. Free bus to lower Duval is...
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    About this property
    Check out the new 'Duval Loop' that ferries you around Old Town for free and is located at the corner of this homes block!!!!Map is included in pictures. Hemmingway House, Lighthouse, Butterfly World, Southern Most Point, Conch Tour Train, Beach, Galleries & Restaurants are all located within a 5...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in beautiful Key Largo, Florida (MM99.2), Zappie's Place is truly an unique property. Enjoy your own private beach situated on the bayside on nearly an acre of tropical property. Fishermen, bring you small boat and launch from our bayside ramp and have direct access to the backcountry...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    BAYSIDE CONDO WITH BOAT1 / 12
    (8)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Waterfront
    • Grill
    • Air Conditioning
    • Outdoor Dining Area
    • Internet Access
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 March 2018
    Spotless condo, great boat and helpful friendly owner J ! Good location, convienent to restaurants and shoppingSecond visit , will be back!
    Reviewed 25 April 2016
    The apartment was lovely. The owners just need to update it a bit. One of the drawers was falling off in the kitchen and two of the chairs were broken. The balcony netting had...
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    About this property
    Bayside condo in a 10 unit complex overlooking dock and canal. This unit is located in the center of Key Largo with access to shopping and great restaurants. Perfect for the avid diver or fisherman as there is a dive shop and bait shop located in the complex. This is a 1 bedroom with a King bed...
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    Location Information
    Key Largo, Florida Keys 33037
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Keys Yacht Vacations! 3 BR (4bed) 2 BA Luxury Yacht-Sunset Cruise avail1 / 18
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Washer
    • Waterfront
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2018
    We had such a wonderful time! The yacht is very nicely equipped & we all slept very comfortably! The marina is top notch too! The first day we arrived, a manatee came right...
    Reviewed 20 January 2016
    We had such a great time staying on the Key West Yacht and Breakfast, It was definitely a different experience staying on a boat but we had such an amazing time. It was so...
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    About this property
    Tourism permitted again starting Oct 1! Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 10 days please contact us for reduced rates! Cruises can be added on for additional fee. Fully equipped from bow to stern -- Galley (kitchen to the...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Grill
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in tranquility at 'Windley Cottage', located at 129 Anglers Way in Angler's Reef, Islamorada's premier gated oceanfront community of 52 private homes, built in 2008. With two luxurious bedrooms, each with its own full en-suite bathroom, it's the perfect vacation property for single families...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Key Largo 2/2 Tropical Daze Oceanfront Condo1 / 32
    (35)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • Hot Tub
    • Waterfront
    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2017
    This condo was very comfortable and nice. It was near enough to groceries, etc., but tucked away. I'd be very happy to stay there again.
    Reviewed 4 July 2017
    Very nice place to launch all your Key Largo activities from. Close to a grocery store and restaurants. Pool was nice with a bar if you needed a drink. The house was in great...
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    About this property
    WE'RE BACK! After 5 months recovering from Hurricane Irma, our completely renovated condo and resort is the #1 place to stay in the Upper Keys. Enjoy our lovely 2/2 right on the ocean, offering spectacular views of the purple and aquamarine waters surrounding Tavernier Key. Safe, gated resort...
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    Key Largo, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Atlantis House Master Suite1 / 22
    (23)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Patio
    • Hot Tub
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 December 2017
    We stayed two nights in the Master suite. (Our second time at the Atlantis House)It was another beautiful experience- everything was prepared with special care from the Turkish...
    Reviewed 18 December 2015
    My husband and I stayed with Kayla and Steve for five days and it was the most relaxing fun filled stay ever. The accommodations were very clean and our hosts were the...
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    About this property
    About Us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique Guesthouse with only 2 suites... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cottage w/ Free Paddle Boards, Kayaks, Sailboats, Water Toys, Docks & Sunsets1 / 26
    (1)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Mermaid Cottage is located between the Jungle Cottage and the Manatee at the aft of the property. It has been nicely painted with coral reef and mermaid setting by a well-known Canadian artist. It has a queen size bed, 1 bunk bed which can sleep 2 kids, kitchen and dining utensils, microwave,...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 1 bathroom with water views! We are renting our comfortable yacht carver 32' to you enjoy the keys on the water! Our yacht has 2 heads 1 queen bed and 1 twin bed , 1 bathroom, kitchen, TV and DVD, dinner table and all the amenities that a house can offer. The boat has 2 AC , 1 in the...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful two story townhome in a private, gated community with all of the amenities you'd expect while on vacation. Inside: Newly renovated and remodeled unit. Fully equipped kitchen and stainless appliances, large storage cabinets with pull outs. Granite counters etc. Living room area with 60...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Private Island Rental with 19' Boat, Seabird Key1 / 51
    (11)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2016
    Seabird Key was absolutely perfect for our family. We were were a party 4 adults, a 2 year old and an infant. The island was well-suited for all. We enjoyed going to the beach...
    Reviewed 20 March 2015
    Wow. Seabird Key is one of a kind. We felt like we were in the swiss family robinson movie. The house's main floor is perched at the same level as the tree canopy. If you...
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    About this property
    Seabird Key is a ten acre private island available for rental by the week featuring an architecturally stunning home with gracious porches and multi level decks; a private, sandy beach and beautiful, tropical gardens throughout. Only 5 minutes offshore by boat, this is the Island that has it...
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    Location Information
    Marathon, Florida Keys 33156
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    A Touch of Bermuda in Key West1 / 19
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 October 2017
    By the time you arrive, you will already feel like you are part of Jack's family. He will literally bend over backward to accommodate you. We have vacationed in Key West for...
    Reviewed 15 July 2017
    I stayed in Jack's condo (a touch of Cuba in Key West) this past week and we enjoyed every aspect of it. The condo is two bedroom one bath and was perfect for my party of three...
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    About this property
    Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is just past the...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Captain's Unit can sleep 2 adults and 1 to 2 kids. It is a one-bedroom suite with its own Jacuzzi tub and a tiki shower. It has 1 king size bed, which also faces the water. An additional bedroom with 2 single beds (bunk bed style)which can be opened for this cottage making it a 2 bedroom. This...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Open for business after Irma.  Private home with Beach Access1 / 68
    (82)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Balcony
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2018
    We had a family of five stay here. It was a good layout with 2 bedrooms and 2 bathrooms. We didn't spend a lot of time in the place as we were sightseeing. We did cook out one...
    Reviewed 21 March 2018
    We stayed in Dan's vacation home for three nights in March 2018. As we had two kids and two couples with us, the layout of this home - two bedrooms with queen beds and a queen...
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    About this property
    We sustained minimal impact from Hurricane Irma and repairs are completed. Our hearts go out to all of those that have not been as fortunate as us. We are waiting to accept your booking. The Keys are open and the sun is shining. Rent with confidence. We have stilt home with newer roof and brand...
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    Location Information
    Key Largo, Florida Keys 33037
    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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    Pet friendly
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    Smoking allowed
    About this property
    The Owner’s Cottage is also right in front of the bay with 2 bedrooms; it can sleep 2 adults and 1 to 3 kids. The main bedroom has a queen size bed; the second bedroom has a queen size loft bed and a twin bed on the ground floor. There’s also a full size pullout sofa bed in the living room. The...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
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    About this property
    Keys home in Anglers Reef with ocean view, dock, community pool & private beach This magnificent home with ocean views from all 4 balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef, a quiet oceanfront community in the Florida Keys. Anglers Reef...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    The elevated queen-sized bed in the Keys Cottage is surrounded by a unique wall mural and has a super-comfy memory foam mattress. Decorated with a Spanish pirate influence, the cottage also features a kitchenette with small fridge, stovetop, toaster, coffee machine and complete kitchen and dining...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    The Main House, a fully furnished 2-bedroom split-level house facing the bay. Features include private patio and barbecue, two dining areas and a large living room. The masters bedroom located at the top of the stairs contains 2 queen size, large closet, and an adjoining bathroom. The neighboring...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Seaside Condo 2 pools summer specials1 / 17
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Secure Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2016
    This apartment was the perfect place to experience Key West, it was sunny and quiet, right across the street from the beach and just minutes away to Old Town with it's great...
    Reviewed 12 March 2016
    This Key West getaway condo is a wonderful escape from the freezing temperatures of the northeast. I was here other years and noticed this time that there is a beautiful new...
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    About this property
    This delightful sunny, quiet apartment is located across the street from Smathers beach and just a ten minute drive to Old Town. The apartment is set in a large lush tropical garden with two Olympic size swimming tools, tennis court, shuffle board court and outdoor lounging and dining areas, It is...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sandy Beach, Direct Ocean, Pool, Dock & Lagoon1 / 34
    (31)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
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    • Waterfront
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 January 2018
    We were warned that all was not in working order because of the hurricane but inspire of that we found the house to be beautiful and spacious, with the help of 2 xtra mattresses...
    Reviewed 2 April 2016
    We could not have been happier with the house! The grounds are beautiful, and the house was perfect! Everyone had a great time and we all want to vacation at the house again!
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    About this property
    WARNING: DO NOT WIRE MONEY Casa de Lida large estate with 3 separate buildings on almost an acre of land and is directly on the ocean . It is very private, has large sandy beach, a pool, a large dock and phenomenal views. The Kids will enjoy playing in the sand, and the adults will enjoy...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated keys cottage. Classic and charming design with modern amenities. This is a concrete home on the ground level, not a trailer or mobile home. Master suite with bath on ground floor. Two bedrooms upstairs with balcony overlooking Buttonwood Sound. Lots of room for the whole...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautiful Large 2BR KINGs (or twins) condo,deck and patio, Truman Anx, Pool1 / 18
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 May 2017
    We spent two weeks at the shabby chicken. The condo was very comfortable, well-stocked, two large bedrooms. The patio was a wonderful retreat for conversation, relaxation...
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    About this property
    The completely renovated Shabby Chicken - come stay with the large and proud newest bird in town!! 5-STAR rating and the best floor plan around. This ground floor, sunny, exceptional, OVERSIZED floor plan with lots more room is only offered in 2 other units in the Truman Annex Shipyard. LARGE &...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southern Diversion Estate Key Largo fall Special open for business post irma1 / 26
    (2)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 17 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 February 2016
    My family & I stayed here from January 27 thru February 3rd. I had my wedding here on January 30th. This estate was absolute perfection! The Keys is a "mixed bag&quot...
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    About this property
    Southern Diversion Estate Key Largo - Brand New private gated 1 acre estate on the ocean with private beach, tiki hut , tropical private pool and deepwater dockage. There is 105ft of deepwater dockage. Docks provide up to 100amp service and water. There is a deepwater channel right to the dock...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 17
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome from Sally and Andrew We look forward to sharing warm tropical breezes and beautiful clear turquoise seas set amid our little slice of Keys Paradise. Feel a sense of Life, Light and Love in our modern, spacious and well maintained Home. Set in an Oceanside location, surrounded by Breezy...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Balcony
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Watch the sunrise from the spacious balcony overlooking the Atlantic Ocean. This brand new three bedroom, two and-a-half bath condominium sleeps eight people. Master bedroom has a king bed with access to the balcony. Second bedroom has a queen bed and third one has two twin beds. TVs in every...
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    Location Information
    Islamorada, Florida Keys 33036
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of Islamorada, Florida. This home features a private beach, 5 bedrooms, 3 ½ baths, family room, living room, game rooms, pool and bar. This home can comfortably accommodate 10-12 people with room to spare....
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Sailfish Cottage is right in front of the bay and has it's own tiki hut facing the water with my personal favorite, a tiki shower for 2 containing 4 relaxing shower heads. It's a freestanding cottage which sleeps 2. We also call this cottage the Honeymoon Suite. Please call/email for...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
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    • Private Garden
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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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    Villa Marquesa in Ramrod Key Florida keys1 / 29
    (14)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Internet Access
    • Porch
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 May 2016
    Beautifully decorated home on a corner canal. It is so close to Looe Key reef that it felt as if it was in our backyard. I highly recommend this home to stay in.
    Reviewed 20 April 2016
    Villa Marquesa is great -- super clean, comfortable bedrooms, lots of towels, everything you could think of is in the kitchen, fans galore and a/c. House is as pictured except...
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    About this property
    House and AMERICAN CARRIBEAN VILLA near to Key West, Florida in Ramrod Key, visit: www.villamarquesa.com for our Official Prices, Calandar and Photos and for our Sister Property Casa Serenity http://www.flipkey.com/ramrod-key-vacation-rentals/p300040/ See us in on TV as the most affordable rental...
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    Location Information
    Ramrod Key, Florida Keys 33042
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    The Dolphin Cottage is a nice freestanding cottage located aft of the Captain’s Unit. Although this unit does not face the water it is only about 100 feet to the beach, waterfront tiki hut, sailboats and water toys. It has beautiful screened in patio and can sleep 2 adults and 2 kids. It has a...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Private Garden
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    About us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique.... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both rooms to accommodate up to 4....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay. Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget all the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    WATERFRONT /DOCK/ POOL/ WALK TO CABANA BEACH CLUB *FALL SALE* 9/8-12/14  $1195WK1 / 27
    (34)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    While searching for the perfect vacation property in Florida Keys for my family of 6 (aged 24-59) I found Casa Mar Azul 1V. We arrived at the house and it was exactly as shown...
    Reviewed 4 January 2016
    I almost hate to give this such a great review as it maybe hard to find occupancy in the future, but this place was in a great community, good location, really nice rental with...
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    About this property
    Welcome to Casa Mar Azul 4, an upscale and luxurious 3 Bedroom, 3 Bath Renovated Pool home that sleeps 8 people and located at 161 10th Street in Key Colony Beach. Just a 1 minute walk to the Private Inch Beach and putting your toes in the beach sand of the Atlantic Ocean. Do you prefer to be at...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    P27 Sunsplash Paradise - Pool home with private beach access!1 / 50
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 December 2017
    This home was EXACTLY as described and pictured. Extremely clean and nicely furnished. It was very quiet and we were able to take a much needed RELAXING vacation! Nice pool...
    Reviewed 5 July 2017
    This home was exceptional and extraordinarily clean, clean, clean! The home was well equipped and I loved the furnishings, decor, beds, quiet atmosphere and I could go on! We...
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    About this property
    Now offering Private Beach Access! 'Sunsplash Paradise' is a dreamy three bedroom, two bath home located in a prestigious neighborhood on Key Colony Beach. But it’s more than that – it’s a place in paradise to create many happy, fun and sun-filled memories with family and friends. We wanted to...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Canal Front Tropical Paradise Awaits as you enter this spectacular 3 bedroom, 2 bath home. Enjoy the tropical decor through out this exquisite house; bedding consists of 1 King and 1 Queen, 2 twin beds. Have fun with out leaving the comforts of home with the private, heat optional pool. Be...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
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    • DVD Player
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1,700 sq. ft. townhome is newly renovated and just a short walk to Sombrero Beach! Unit includes tile flooring, kitchen w/ stainless steel appliances and granite counter tops, remodeled bathrooms and new furnishings throughout. Enjoy the community swimming pool and BBQ located along a...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Billy's Blue Heaven at Truman Annex:  2 Balconies, 2 Bikes, and a Pool1 / 32
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Balcony
    • Waterfront
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    What a lovely condo! It is beautifully appointed! The bed in the master was very comfortable, the bathroom was very nice, loved the shower with 2 shower heads! Nice sized...
    Reviewed 3 weeks ago
    The condo was charming and perfect. The complex is beautiful and in the perfect location. I would highly recommend staying at this condo.
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    About this property
    Billy's Blue Heaven is fresh, clean and Pristine. Just a two minute walk to Duval Street and only 300 steps to the world famous Ricky's Blue Heaven Restaurant. The balcony overlooks Truman Annex 's lush landscaping beside the shared swimming pool. A very short walk or bike ride to Fort Zachary...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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