- 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
Recent Key West reviews
"This is a charming place! Well decorated and has everything you need. It is right off Duval street but is very quite and peaceful. If you go to Key West you must stay here!"Guest: Randy Date of Stay: June 2014 Review Submitted: June 12, 2014View listing
"My wife and I spent our honeymoon at the Pirates Quarters and it is everything that the previous reviewers have stated and more! Checking in was a breeze and the owner Heather was there to greet us that evening and with lots of information and a quick tour of the rental. I really can't say enough about how awesome and helpful the owners are. Any time we had a question about the unit or island they were just a call or text away and Heather recommended a restaurant that ended up being one of our most memorable nights. As for the rental property itself, it was perfect. The kitchen/living space was spacious with updated decor and appliances. Having a full size fridge was great for storing beverages and food. The bedroom was the perfect size and very cozy with the dark wood. Bed was very comfortable, slept great. Bathroom was very cool and had a great island feel. Oversized shower with two showerheads=amazing. The BEST part was the huge front patio. We probably spent most of out time here when we weren't out in the city. Gas grill came in handy, we brought back some fish that we had caught from an excursion and were able to make a great dinner. Patio furniture was comfy and we were able to just sit outside relax and wave to locals as they walked by. As for the location, you really can't ask for a better one. Just 2 blocks, or maybe a 5 minute walk to the center of Duval St and all that it has to offer, although the neighborhood the property was located in was quiet and very private. The famous Blue Heaven Restaurant is literally right down the street on the corner(we ate/drank there several times), same with Hemingway's House. Right next to that are Santiago's and Firefly. Make sure you try the fried Pig Ears at Firefly! Fort Zach is a quick 10 min bike ride. Oh and take advantage of the bikes on the property. Spending time all over the island I am convinced there really isn't a better location to stay and be so close to all that Key West offers. The Pirate Quarters will definitely be #1 on our list when we return in the future. Thank you Heather & Dave!!"Guest: Greg W Date of Stay: June 2014 Review Submitted: August 10, 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
"This was our first vacation rental through VRBO. We were extremely pleased. This condo was just as described with no surprises. Rosemary, the owner, was excellent to deal with. Very professional and all our questions were answered promptly. The condo was perfect with a great layout. Everything we needed was available and it was ultra clean and meticulously well cared for. The location could not have been any better. Very private and quiet with easy access to EVERYTHING that is Key West. Patty, the local property manager was a pleasure to deal with also. Excellent communication and always available if needed. When the week was over, our security deposit was promptly refunded within 48 hours of leaving. I would highly recommend renting from these owners. They are very ethical and a pleasure doing business with them. We will surely rent from them again when the opportunity arises. Thanks for a great vacation!!"Guest: Joel Date of Stay: June 2014 Review Submitted: June 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.