- Duval Square
- Harbour Place
- Key Haven
- Key West Beach Club
- Key West Cuban Club
- Key West Golf Club
- La Brisa
- Oceanside Marina (formerly Kings Pointe)
- Pelican Landing
- Private Homes, DownTown
- Private Homes, Historic Seaport
- Private Homes, Mid Town
- Private Homes, New Town
- Private Homes, Old Town
- Private Homes, Unspecified
- Private Homes, UpTown
- Seaside Resort
- Shark Key
- Southard Square
- SouthSide Resort
- Sunrise Suites
- Sunset Key
- Sunset Marina
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
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Recent Key West property reviews
"I have stayed in the community for the last 5 years and truly enjoy the home. It is within easy walking distance to Duval St. and the beach at Fort Zachary Taylor State Park. Everything you need to enjoy your time in Key West is included, and if there is a problem, the owners are quick to resolve it. The neighbors inside the compound always make us feel welcomed and over the years, we have developed a friendship with them. This is by far the best vrbo unit we have stayed in at any location. We are looking forward to returning Jan. / Feb. 2013 and for many years to come."Guest: key west wannabe Date of Stay: January 2012 Review Submitted: June 2, 2012View listing
"We, two couples, just spent time at Kaley's Cottage and it was amazing. Truly like having our own slice of paradise. PERFECT location too! How often is a place even nicer than the pictures?? This one is! The living room was updated from the pics and wow! The pool was an oasis and a delight to do morning yoga and to cool down after a day out before getting ready to go out for dinner. The kitchen was fully equipped with upscale appliances and accessories - even a wine refrigerator! The place had so many extras, books, cd's, music system.... The owners were delightful - they booked our excursion and gave us great discounts to local places!! Location, location, location that was a place with more than one would expect. Thanks for sharing your paradise with us!!!"Guest: Campquail Date of Stay: July 2013 Review Submitted: July 30, 2013View listing
"This house was exactly what I was looking for. I wanted a place that I could sit in 1 spot and watch the sun rise and the sun set. I was able to do that at this property. All I had to do was turn around. The house was as beautiful as the pictures. I would highly recommend a vacation to this house. We had 4 couples and we all had a wonderful time and thoroughly enjoyed the pool and the fantastic ocean views!"Guest: Debbi Date of Stay: November 2012 Review Submitted: December 12, 2012View listing
"What a great find the Captain's Mansion is. It was the perfect place for our two families during our summer 2011 trip to Key West. We found the owners to be pleasant and very easy to work with before, during, and after our stay. The Captain's Mansion was perfectly located for us. We arrived by boat and were pleased to discover it was only a 3 block walk from the Marina. It is an easy walk to the heart of Key West and just a few blocks from a grocery store and a variety of really good restaurants that were recommended by the home's owners. The pool, outside shower, and inside/outside bar were an ideal place to come home to after a day of roaming the island and snorkeling at Sand Key. Upon arrival we were thrilled to find the house to be as clean, attractive and well maintained as depicted in the photos. The kitchen was top-notch and well equipped. The rest of the home was a nice combination of recent renovation and gorgeous original detail. We would certainly recommend the Captain's Mansion to family and friends, and hope to return in the future."Guest: Team Tampa Date of Stay: June 2011 Review Submitted: September 6, 2011View listing
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.