- Private Homes, New Town
- Private Homes, Old Town
- Private Homes, Unspecified
- Private Homes, UpTown
- Salt Ponds
- 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
- Coconut Beach
- Coconut Mallory
- Coral Hammock
- Duval Square
- Harbour Place
- Hyatt Beach House Resort
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
"My husband and I just returned last night from a 6 week stay in this lovely tropical townhouse at the Key West Golf Club and are already planning next year's return. The place is clean, nicely furnished (just as pictured on this website), close to one of the Club's beautifully maintained and landscaped pool areas, neighbors are friendly and helpful as are the security folks, fine artwork graces the freshly painted walls. This vacation home has lovely, new tile flooring throughout, which along with the wipe-able blinds and quality mattress and pillow encasements in the master bedroom make for an almost dust-mite proof sleeping experience. The surrounding grounds at the Golf Club are lush and tropical, beautifully landscaped and maintained, reminiscent of Old Town Key West but without the noise and craziness. Amazing experience. In all the years we've been renting in Key West to escape the cold northeast winters, this is the first place we've wanted to return to!"Guest: Mary Anne Date of Stay: February 2014 Review Submitted: March 16, 2014View listing
"This condo was absolutely fabulous! The kitchen is well equipped with everything you need. Everything worked and very clean. Unit has a ton of towels (bonus!). Perfect spot for watching the ships come and go and the Key West sunset! Convenient to Duval and many great places to eat. The pool at Harbor place is fantastic! I hope to come back to this condo again soon!"Guest: Tennessee Gal Date of Stay: September 2014 Review Submitted: October 24, 2014View listing
"There were 6 adults. It was a very clean and served our purpose for 3 days? Yes I would return to the Cubian. WiFi did not work. Called and instantly received a call back. Right on Duval Street. Unit upstairs and huge front deck. Would return again! Highly recommend!🌴☀️"Guest: Linda S. Date of Stay: November 2014 Review Submitted: December 7, 2014View listing
"We rented Jeff's place from the middle of October to the middle of November, a great time to be in Key West...the Zombie Bike Ride, Goombay Festival, Fantasy Festival, World Powerboat Championships, etc....always something to do. This is the first time we have rented outside of the Historic District and I would say that Seaside Resort exceeded our expectations. The place is wonderfully decorated, is furnished with everything you need in your home away from home, the outdoor patio and grill were a favorite of ours and we loved the location....easy access to the Historic District and all the events (as long as you have a car or bike) yet away from the crowds of Duval St. The clubhouse pool was great and we were an easy walk away from the ocean and Smathers Beach. Best of all we didn't have to constantly search for an overnight parking spot. It was also conviently located near two of our favorite local's watering holes, Hurricane Hole Marina (great fishing with Triple J Fishing Charters) and Hogfish Bar and Grill. I would highly recommend this townhouse for your next long-term getaway in Key West."Guest: Mel Date of Stay: October 2014 Review Submitted: December 13, 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.