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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

  • awsome

    "the place was clean and as describe a nice quiet little get away surrounded by beauty and excitement"
    Guest: Daniel W. Date of Stay: February 2014 Review Submitted: April 19, 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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  • Great Location - Comfortable with Key West Character & Charm!

    "Our family of four (kids ages 12 & 14) stayed in the Caribbean suite 3 nights over Super Bowl weekend. We prefer VRBO properties over hotels. I searched many listings before finding this place. Similar listings did not allow guests under 18, nor offer a pool and were higher priced. The location is great – only a few blocks from Duval on a quiet street and a 20-minute walk to Mallory Square. No problem finding parking on the same street block. The pool was heated and the brick courtyard had lounge chairs, sunny and shady spots to sit, and a fountain that provided a relaxing background sound. There are 7-8 individual (condo-like) properties within the Hollinsed House complex. The Caribbean suite has a nice outdoor space with the private front porch. The interior is a good size with a comfortable living area and bedrooms with drawer space. The furnishings and accessories are a bit eclectic but the home was clean and well stocked with plenty of towels for the bathroom and pool, toilet paper, and paper towels. The kitchen is small but recently updated and functional. The bathroom is also small and could stand to be updated but overall, it was functional and clean (though the grout in the bathroom tile shower could be cleaner.) If you need to do laundry, you can use the shared washer/dryer for a nominal fee after the housekeeper is finished for the day. Wi-fi worked great. Our only complaint was the small 20-inch TV in the LR. We didn’t want to drag the boys out to a bar to watch the Super Bowl so we had to watch the game on this TV. Not the best for my fanatical football fans! With flat screen TVs so inexpensive these days, the owner really should spend a few hundred dollars to upgrade. The property manager, Tracey, was very friendly, responsive, and easy to work with – we spoke by phone and email and she answered all of my questions. Check-in was easy and exactly as described. I called her on our departure day to let her know about a couple of minor repair items along with our suggestion to upgrade the TV. She was very receptive and appreciative of the info. Additionally, the housekeeper, Ruth, is very nice and helpful. Overall, this place is a great find if you are looking for: a convenient and quiet location; old Key West charm and character; and comfortable/clean accommodations with a pool. If you prefer everything new and modern with designer décor, stay at a fancy hotel and pay a lot more. We hope to get back to KW and stay here again. Thanks Tracey!"
    Guest: Sandy K. Date of Stay: January 2014 Review Submitted: February 25, 2014
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  • Fabulous stay in every way!

    "This was our first time staying at the Hollinsed House, but it definitely won't be the last! The house and grounds were beautiful and the "Poolside Suite" was perfect for two people. The location couldn't have been more convenient for Fantasy Fest and general sightseeing (within easy walking distance of Duval Street, the Cemetery, etc). Ruth the housekeeper was a gem and was very attentive to our needs. We were as comfortable as we've ever been in a vacation rental -- it felt like home! Tracey was easy to work with and we had no issues. I couldn't recommend the Hollinsed House more!"
    Guest: Adam S. Date of Stay: October 2014 Review Submitted: November 11, 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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