- Private Homes, UpTown
- Seaside Resort
- Shark Key
- Southard Square
- SouthSide Resort
- Sunrise Suites
- Sunset Key
- Sunset Marina
- Truman Annex
- Villas Key West
- White St. Gallery
- Windward Park
- 1800 Atlantic
- Bahama Village
- Casa Marina
- Coconut Beach
- Coconut Mallory
- Coral Hammock
- Duval Square
- Harbour Place
- Key Haven
- Key West Beach Club
- Key West Cuban Club
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 property reviews
"My husband and I just spent a month in the Tree House and loved every minute of it. The deck is a wonderful place to relax either lounging in the hammock, sitting in the lounge chairs or just sitting at the table eating your meal. We also enjoyed the generous hospitality of the owner who went out of his way to please. The location is also great for walking to "whatever is happening" on Duval Street or the Historic Seaport. We are going back!"Guest: Eva Date of Stay: January 2014 Review Submitted: February 14, 2014View listing
"Great location! This was our third year staying at the Cocunut Beach, a quite spot on the ocean, and a short distance to the south end of Duval Street. You are a bike ride or walk away from state park, restaurants, bars, and many of the historic sites of Old Key West. Usually just the two of us, but this year we had 2 other guest for part of the week and accommendations were very comfortable. The property is well kept and very clean, bike rentals and activities are available on the property. Can't wait to go back next year."Guest: Steve and Janet Date of Stay: January 2013 Review Submitted: February 13, 2013View listing
"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
"My husband and I rented this property in May, 2014. The property is absolutely beautiful and we loved our stay. The house is beautifully decorated and extremely comfortable. The staircase might be a concern for anyone with small or young children as it is unusually designed and would be a hazard to children or toddlers. The two upstairs bedrooms each have a queen size bed and private bath. Washer and dryer came in very handy for light packing. Although we ate dinner out most nights, We ordered groceries from Fausto's Food store on Key West and they delivered them to us for $5.00!!! What a bargain and their specialty items (shrimp salad and specialty cheeses) were incredible. The resident's beach is secluded and very nice. The house manager, Bob, was extremely welcoming and helpful. The gardens and flowers were amazing and beautifully tropical. This property is lovely and we will definitely return!"Guest: Love Key West! Date of Stay: May 2014 Review Submitted: June 10, 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.