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This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Recent Key West Area reviews

  • Actually was 10 stars!!!

    "What a PERFECT vacation property! Very classy decor, every item you might need, and all was in tip top shape! The beds and furniture were very comfortable, the pool was perfect and the A/C was fabulous....... It is HOT! HOT! HOT in July! What impressed me the most, is how responsive Dean was to all my questions during the whole process. AND....how responsive his crew was while we were there......we went to use the grill for the first time.....and no gas! A quick call to Paul and within 5 minutes, literally, we were cooking! Fantastic! That says a lot to the care and professionalism of Paul and Dean. We would definitely rent with them again!"
    Guest: sylvia a. Date of Stay: July 2014 Review Submitted: July 24, 2014
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  • Amazing Honeymoon!

    "My wife and I spent our honeymoon at the Pirates Quarters and it is everything that the previous reviewers have stated and more! Checking in was a breeze and the owner Heather was there to greet us that evening and with lots of information and a quick tour of the rental. I really can't say enough about how awesome and helpful the owners are. Any time we had a question about the unit or island they were just a call or text away and Heather recommended a restaurant that ended up being one of our most memorable nights. As for the rental property itself, it was perfect. The kitchen/living space was spacious with updated decor and appliances. Having a full size fridge was great for storing beverages and food. The bedroom was the perfect size and very cozy with the dark wood. Bed was very comfortable, slept great. Bathroom was very cool and had a great island feel. Oversized shower with two showerheads=amazing. The BEST part was the huge front patio. We probably spent most of out time here when we weren't out in the city. Gas grill came in handy, we brought back some fish that we had caught from an excursion and were able to make a great dinner. Patio furniture was comfy and we were able to just sit outside relax and wave to locals as they walked by. As for the location, you really can't ask for a better one. Just 2 blocks, or maybe a 5 minute walk to the center of Duval St and all that it has to offer, although the neighborhood the property was located in was quiet and very private. The famous Blue Heaven Restaurant is literally right down the street on the corner(we ate/drank there several times), same with Hemingway's House. Right next to that are Santiago's and Firefly. Make sure you try the fried Pig Ears at Firefly! Fort Zach is a quick 10 min bike ride. Oh and take advantage of the bikes on the property. Spending time all over the island I am convinced there really isn't a better location to stay and be so close to all that Key West offers. The Pirate Quarters will definitely be #1 on our list when we return in the future. Thank you Heather & Dave!!"
    Guest: Greg W Date of Stay: June 2014 Review Submitted: August 10, 2014
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  • Very Very Nice

    "We've been to Key West a few times and this was our first stay in the Truman Annex. We think we hit the pinnacle with this unit in the Foundry building. Nice inside/outside living with French doors out the front plus a comfortable side yard. The location is excellent, most everything you want in KW is a short walk or bike away. Groceries and other essentials are in an easy walk. The unit is just as shown in the pictures, very comfortable, clean and well equipped. The owner is easy to work with, all communications were well managed. We hope to be back."
    Guest: Paul H. Date of Stay: December 2014 Review Submitted: December 14, 2014
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  • Family time

    "Overall it was a perfect vacation for us. Two families got on like one. Unique environment, close quarters, and no problems! It's far enough away from the noise and trapping of KW but close enough to enjoy it when we wanted. We shared cooking duties , one cook at a time, because the galley is small but that brought out the best in each of us. We had no plans for the entire week except for the day sail with the Captain which was lots of fun. We woke up everyday and decided what we would do... a perfect week!"
    Guest: Scott S. Date of Stay: March 2014 Review Submitted: June 16, 2014
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Key West Area Travel Tips

If some of your favorite things include warm, sunny days, glorious beaches, laid-back atmospheres, literary figures and history, then Key West is the ideal vacation spot for you.

Once you arrive in this Florida city, your tension will instantly melt away as you spend afternoons saltwater or deep sea fishing, sampling the local cuisine at the various restaurants, hiking through the backcountry or exploring the underwater world of coral reefs as you dive and snorkel.

Key West is also home a wonderful literary history where you can learn about and experience a variety of writers, playwrights and poets including, most famously, Ernest Hemingway. However, Tennessee Williams, Robert Frost, Shel Silverstein and Wallace Stevens also made their mark on this Florida hub.

There's something to please everyone here in Key West whether you like to spend your vacation days exploring and having adventures or you prefer to lounge about letting your mind and body relax. Either way, you're sure to have a wonderful time here while you soak up the sun.

Things to Do in Key West

- Ernest Hemingway Home and Museum: Lovers of literature and Hemingway fans must put a visit to the Ernest Hemingway Home and Museum on their list of things to do in Key West. The home served as Hemingway's residence during the 1930s and was the first on the island to have indoor plumbing. Notable features included a built-in fireplace and a swimming pool. Surrounding the home are the gardens, which are stunning in their own right. Tropical plants, lush greenery and colorful florals are lovely to see. One of the most unique and fun features - especially for animal lovers - are the 40 to 50 cats that live here, about half of which are polydactyl (six-toed). Hemingway was given a polydactyl cat by a ship captain and some of the current cats are descendants of that original feline, Snowball.

- Dry Tortugas National Park: Spend some time exploring nature through the almost 70 miles of Dry Tortugas National Park that's mainly open water surrounding seven small islands. Here you'll find sparkling blue waters, Fort Jefferson, amazing coral reefs and a collection of birds flying overhead. Whether you're looking to spend some time bird watching, snorkeling, hiking, kayaking, fishing or a little bit of everything, this national park is one of the best places in Key West to do so. Dry Tortugas got its name from the plethora of turtles found in the area, so keep an eye out for loggerhead, hawksbill, green and leatherback turtles in the waters.

- Key West Butterfly and Nature Conservatory: Enjoy the magic and wonder of colorful creatures and beautiful flora and fauna at the Key West Butterfly and Nature Conservatory. You'll find an expansive collection of flowering plants, birds, waterfalls, trees and hundreds of stunning butterflies. There are 50 to 60 different species here, as well as more than 20 exotic birds. It's a lovely place to slow down and let stress melt away, and kids will have a great time chasing the butterflies and marveling at their patterns.

- Saint Augustine Pirate and Treasure Museum: Ahoy, mateys! Take a break from scouring the seven seas and step back in time to find out if the pirate life is for you at the Saint Augustine Pirate and Treasure Museum. Here you can peruse more than 40 different exhibits featuring the biggest and most authentic collection of pirate artifacts, including Blackbeard's original blunderbuss, gold pieces from his warship - Queen Anne's Revenge, one of three remaining authentic Jolly Roger flags, and Thomas Tew's original treasure chest. There are even hands-on opportunities to see what it's like to fit the wind as you steer the ship and find out what a real cannon feels like.

Dining in Key West

- Blue Heaven Restaurant: For a casual Key West dining experience head to Blue Heaven Restaurant where you can dine indoors or out, watch live entertainment and sample Caribbean (or vegetarian) cuisine. In keeping with the animal theme, cats and chickens roam the premises and add extra fun to your meal. The restaurant is one of the most popular in Key West and favorite dishes include blueberry pancakes, carrot and curry soup, scallops provencale and miso-marinated eggplant salad. Be sure to save room for some of the island's best key lime pie!

- Sloppy Joes: Dining at Sloppy Joes is a Key West tradition. Since 1933, this has been the place to find a welcoming, hospitable staff and a great place to enjoy a night out. Sandwiches, wraps, salads and pizza dominate the menu in addition to a great beer, wine and drink menu. Starting at noon, live entertainment kicks off and continues through the wee hours of the morning, making for a thrilling place to spend time and let your hair down. Sip cocktails while you tap your toes along to the music, or dine on a delicious meal while you enjoy your travel companions' company in this cool setting.

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