- 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
- The Banyan Resort
- Truman Annex
- Villas Key West
- White St. Gallery
- Windward Park
- 1800 Atlantic
- Bahama Village
- Beach House Resort
- Casa 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
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
"Marie and Tom were really great to work with. First time to use VRBO. Marie e-mailed us while we were there just to make sure we had everything we needed. Super nice. I told her when we left that the pillows were flat and she e-mailed me back that the cleaning lady would replace them. The beds were alittle firm for me. I like my beds softer. The condo is at the very end of the annex. We rented scooters. My wife loved them. The Truman Anex is a wonderful place to stay. The grounds are first class."Guest: Barry W. Date of Stay: September 2014 Review Submitted: October 16, 2014View listing
"We absolutely loved our stay in this unit. Very spacious unit with nice amenities and all updated. The location was terrific and within walking distance to everything! Highly recommend fo your stay in Key West, you will love it!"Guest: Al Date of Stay: August 2014 Review Submitted: September 1, 2014View listing
"Wonderful condo. Beautiful on the inside and the outside. Perfectly equipped with all you need and the location could not be better. We drove twice and walked or road the bikes the rest of the time. Washing machine and dryer make packing easier and drying towels a breeze. Everything is easy to operate and easy to find. The Beach at Ft Zachary is beautiful and welcoming and literally within walking distance. It was windy so we were unable to snorkel from the beach. For an excellent snorkeling experience, contact Looe Key Resort on Ramrod Key for the best snorkeling you will experience. Take the afternoon trip and enjoy the great crew and the free drink tickets from the Tiki bar. They treated us like family and the reef was amazing! And no one could beat their price, its about a 30 minute drive north. We took a boat charter directly scheduled through Fish Check at the Key West Marina and the experience was a good one. Fresh Mahi Mahi for dinner was a welcomed treat. The entire trip was wonderful and BJ was fantastic to work with. Look no further, come home to Truman Annex and relax."Guest: Heather R. Date of Stay: May 2014 Review Submitted: May 29, 2014View listing
"this cottage is in a great location, literrally 1 block from Duvall Street. The courtyard area is very well kept, and has a private pool! The cottage itself was very clean as well when we arrived, the bedroom is a little bright, since its all white, so no sleeping in. But overall a great place and I'd definetly stay there again!"Guest: Kel Date of Stay: May 2014 Review Submitted: June 12, 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.