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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 reviews

  • Fun in the sub

    "Second time we stayed here. Love the location can walk anywhere in Key West. Cottage had everything needed for a week stay and the staff was very helpfull. Would stay again."
    Guest: Scott C. Date of Stay: November 2014 Review Submitted: November 15, 2014
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  • More than we imagined

    "We chose Island Dreams because of the rave reviews and quirkiness of the decor not to mention the ocean view, property amenities and ease in working with the owners. We were delighted with everything about the property. Plenty of linens, well-stocked kitchen, and gorgeous sunrises and sunsets. The bed was so comfortable and the unit very clean. Lots of lighting with dimmers to set the mood. The bikes were great! We did ride all the way to the end of Duvall and back. Much easier to find bike parking. The pool and grounds are well-maintained. We will definitely make this our first choice vacation home next year."
    Guest: Liz N. Date of Stay: November 2014 Review Submitted: December 7, 2014
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  • Perfection

    "We thoroughly enjoyed out stay! The condo is beautiful and very well maintained. The 2 king sized beds were a huge plus! Also, the pool with a gorgeous view made our great afternoon relaxing very enjoyable. The location is perfect. We were able to walk to most of the places we want to visit. We would love to stay here again. Thank you Darla for helping us have an amazing trip!"
    Guest: Melanae A. Date of Stay: August 2014 Review Submitted: September 4, 2014
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  • A little piece of paradise~

    "Rooster Retreat was a wonderful vacation experience! And yes I too will begin with clean...unit is very clean and well maintained. Loved the location, from the perspective of the Truman Annex itself, and from the logistics of being centrally located in Key West. My husband and I use to have a season rental home in California and in my ad I use to say, "just bring a few cookbooks and your spices, everything else is there". The owners could say the same thing, everything you need is there...umbrellas, beach chairs, tons of pots and pans, glasses, dishes, silverware, towels, beach and otherwise...you get the idea! Furniture is very comfortable, king bed is restful, and parking is just a few feet from the front door(great with groceries). Me with a new fitbit we logged in 4-6 miles of walking a day(even with rain) and my husband loved the private garden (no foot traffic) for reading. Having been a Key West visitor for more years than I will mention, we are always looking for new eateries, as well as our favorites...Half Shell Raw Bar for great boiled shrimp, Blue Heaven for breakfast(go early on Sunday), Kelly's for dinner or bar snacks, Santiago Bodega for dinner and Aqua for a fun drag show~ Owners are wonderful to work with, very detailed and timely in the their replies. There is also a wonderful grill to use in the yard, and it is fun to enjoy a private meal in the garden, which is lush with palm trees. The deck in the yard is large enough to spread out a yoga mat and do a few downward dogs, such an added perk! We did so love our visit and look forward to a return stay at the Rooster Retreat or perhaps the new Shabby Chicken. Both are lovely units!"
    Guest: Pat Date of Stay: November 2014 Review Submitted: December 2, 2014
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Key West Travel Tips

Key West is a veritable hot spot for literary icons, both today and in the past. This small Florida island was loved by the likes of playwright Tennessee Williams, and poets Robert Frost, Wallace Stevens and Shel Silverstein.

Today, beloved children’s author Judy Blume keeps a home here, and every January for more than 30 years, writers and readers from around the country gather at the high-profile Key West Literary Seminar - spread over two weekends - for lectures, readings, discussions, workshops and parties. The event has featured the likes of Joyce Carol Oates, Junot Diaz and Gore Vidal.

Key West should be high on the list of travel locations for any literary lover and creative soul because of its deep history in extraordinary American literature. Ernest Hemingway even kept a fabulous estate in Key West that today has been converted into a museum and bookstore. Visit the beautiful and historic Ernest Hemingway Home and then check out some of the writer's rumored favorite spots.

Ernest Hemingway Home and Museum

Hemingway’s stately, olive-shuttered two-story cottage at 907 Whitehead Street in Old Town Key West is no doubt a visitor favorite. If you’re a die-hard Hemingway fan, you’ll have to brave the crowds and come here.

The home was built in 1851 from limestone excavated from the exact land upon which it is built. Hemingway bought and lived in the estate from 1931 until 1940 with his wife and kids before he left for Cuba. This spectacular estate, which includes a rear guesthouse and is surrounded by elegant gardens and rustling palms, is still the largest residential property in Key West.

You might be surprised to see that the beds are made in full linens and the home looks recently lived in - it’s as if the family just stepped out for lunch and will be home shortly. Here are the highlights you should take note of inside and around Hemingway’s marvelous estate:

The Ritzy Pool

A pool this large - or any pool at all - in 1930s Key West was a luxury. To fill it, construction workers had to drill to the salt-water table deep in the ground and install a water pump. Hemingway’s wife - Pauline - had the costly pool built as a surprise for Hemingway while he was in Spain in 1938 working as a correspondent during the Spanish Civil War.

The Happy Cats

Hemingway’s six-toed cats - or polydactyls - are legendary. Recently uncovered letters from Hemingway to a friend explain just how sad he was at the loss of one of his cats - Willie. The Hemingway Home and Museum curators maintain that each of the 40 to 50 cats on the grounds is a direct descendant of Hemingway’s first cat, a white polydactyl named Snowball (Though they don’t all have six toes on each paw, all are said to carry the gene for polydactyly). The cats living here are very friendly and many will actually pose for pictures. They’re all vetted and well-taken care of - not your average strays!

The Lush Gardens

The Hemingway House gardens are stunning, featuring a vibrant array of tropical flowers - shrimp plants, heliconia, bleeding hearts and the funky looking pelican flower - and banana, Barbados cherry, papaya and Spanish lime trees, among many others.

Other Literary Tour Stops

410 Caroline Street is Jessie Porter’s home - a fifth-generation Key Wester - who was good friends with Robert Frost. He spent several winters in the cottage in Porter’s backyard. The site used to be the Heritage House Museum, though it has been closed since 2010. If you want to see things the iconic Frost saw, at least take a stroll past the home!

Green Parrot Bar and Sloppy Joe’s Bar are rumored to be hangouts of Hemingway and his friends like Wallace Stevens.

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