- Harbour Place
- Hyatt Beach House Resort
- 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
- The Banyan Resort
- Truman Annex
- Villas Key West
- White St. Gallery
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 reviews
"We loved relaxing and fishing right on the canal! We also went charter fishing with the neighbor a block away and that was awesome to be so close! It was a great location to be away from it all, but yet a short drive away from the action of Key West. Geiger Key is a great place and we enjoyed our time there! We used the kayak several times to explore around Geiger Key and that was a lot of fun! The owners were very easy to work with and super helpful! This was not an issue for us, but others may need to know that the rental is on the second story of the property, so if stairs are a problem you might need to look somewhere else."Guest: Kate E. Date of Stay: November 2013 Review Submitted: February 20, 2014View listing
"Great Condo. Had a lot more space that pictures show. Great Location right in the middle of everything. Being able to wash clothes was a plus+++ so you do not have to pack much. Beach is a bike ride away as well as the pool is walking distance. Kitchen had every needed if you choose to shop at the local supermarket and save yourself some $$ from eating out daily. Also has a Grill out on the private patio. Property is very well kept. Got to meet the owners Richard & Betsy very nice people. Look forward to booking my trip for next year. Thanks Richard & Betsy."Guest: KATHLEEN K. Date of Stay: November 2013 Review Submitted: November 18, 2013View listing
"This is a wonderful condo in a residential neighborhood of Key West. You have a sense of what it is like to actually live here. The condo is comfortable and peaceful, and has a good sized pool with beautiful landscaping in a common area in back. You do not need a car, but a bike helps if you want to go to Mallory Square for sunset. The condo is located near White Street, which has restaurants, local cafe con leche, and Faustos market. The condo has a fenced front porch which is great if you are bringing a dog, and Bayview Park, where you can walk your dog, is two blocks away. I loved staying here."Guest: shiro Date of Stay: April 2014 Review Submitted: April 18, 2014View listing
"This was my 4th visit to Key West so I knew what area of town I wanted to stay in for a month long vacation and the Poorhouse Lane property couldn't have been more ideal as far as walkability to all the Old-Town sights. Duval is a short walk, but I did love that it was on a quiet street. The neighbors nearby are charming (especially Joseph who lives across the ally and was always ready with a good recommendation of restaurants for dinner) While there is no parking with the property we never had a problem finding on-street parking about 100 feet from the front door (in front of Jimmy Buffet's house). The house isn't huge (Most Key West homes aren't) but the layout and three bedrooms afforded us enough privacy for us to relax and get some quiet time if we needed it. The property management company that takes care of the house for the owners was very accommodating and tried to rectify an problems that we had during our stay. The gas grill stopped working, and Kevin the property manager arrived with a new one within two hours. I had realistic expectations this is a home and not a hotel. So there isn't daily housekeeping, and not everything is 100% pristine but I was found the house to be warm and welcoming and felt comfortable there. My only complaint was that the pool heater was broken for 3 of the 4 weeks we were there. The pool water wasn't freezing but a little to chilly for a wimp like me. I would certainly recommend this property to friends and would consider staying there again if we were lucky enough to go on another month long vacation. With rental rates for Key West being pretty high I found the rent to be far, and I appreciated that I was able to bring my dogs for an nominal fee. Thanks Soren and Irene for a great stay!"Guest: mcnelson Date of Stay: December 2013 Review Submitted: January 28, 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.