- Windward Park
- 1800 Atlantic
- Bahama Village
- Beach House Resort
- Casa Marina
- Coconut Beach
- Coconut Mallory
- Coral Hammock
- Duval Square
- Harbour Place
- Hyatt Beach House Resort
- Hyatt Windward Pointe
- Key Haven
- Key West Beach Club
- Key West Cuban Club
- Key West Golf Club
- La Brisa
- La Casa de Luces
- 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
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
There are no vacation rental listings in Key West currently advertising. Please see the USA, Florida, Florida Keys, Key West Area vacation rentals page.
Recent Key West Area reviews
"We absolutely loved staying at this condo. It was perfect for us and could not have been any better. The place is exactly as described, cozy, spacious, private and quiet, sparklingly clean and very comfortable. There was plenty of room for the three of us. The kitchen came with everything we needed. We had bath towels, beach towels, books, TV in every room, which we never used ;-) helpful information about the house and surrounding area. Views from the back veranda are amazing. We spent so much time outside, having breakfast, reading, relaxing, talking. There was a pool as well and we seemed to be the only ones using it at that time. We really loved the location and the quiet atmosphere. We were able to get to Duval and downtown in less than 15 minutes but we were also far away enough from the hustle and bustle to get some peaceful sleep at night. Cynthia, the owner, was awesome! A very cool, super nice, easy-going person, always helpful with any questions we had. She gave us many tips, where to go, what to do, where to eat. It was our first trip to the Keys and staying at Cynthias Ocean Front Condo made our vacation a wonderful experience. Thank you Cynthia for everything and we are really looking forward to staying at your Condo again :-)"Guest: Sabine Date of Stay: September 2014 Review Submitted: October 15, 2014View listing
"Being from Colorado we have little access to the type of experience offered by Captain Bob. We greatly enjoyed staying on his catamaran as well as the day sail. He was easy to reach, conscientious, knowledgeable, very upfront with details - more than meeting our expectations. Our sons loved the snorkeling and kayaking. Plenty of towels and extra items on board if something is forgotten. Cannot wait to do this again!"Guest: Mary Date of Stay: September 2014 Review Submitted: September 20, 2014View listing
"This home provided all the comforts of home. The photos provided do not provide or showcase the charm of this home. The side deck of the yard had a tropical flare that was amazing for evening barbecuing and gathering. This home provided all and more my sister could want for her 50th birthday she loved it, my sister-in-law and brother celebrating 20 years of marriage loved the master suite which was quite lovely. Finally, the location was perfect for being a tourist during the day and far enough away to have the comforts of a quiet neighborhood for evening relaxion. Another great feature of this home is it appears to be newly remodeled, beautifly decorated, family photo that brought warmth of the owner, and the cleanliness of the home was an extension of the owner's way of providing those who visit a sense and feel of a home away from home! Alma H."Guest: Alma H. Date of Stay: November 2014 Review Submitted: November 29, 2014View listing
"Stayed for 10 nights. This condo was comfortable and spacious. Nice decks off the living room and master bedroom. We have been staying at the Truman Annex complex (Shipyard Condos mostly) for many years. This is now one of our favorites."Guest: Pete & Eric Date of Stay: May 2014 Review Submitted: May 30, 2014View 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.