- 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
- Key West Golf 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
- Villa Soleil, Elegant Truman Annex Condo in Old Town Key West 2 Bedrooms 1 Bathroom Sleeps 4 Truman Annex #188516ha
$5,000 - $8,500 per month 28 night min stay
- Key West Oceanfront Condo - 'the Sea Jay' 2 Bedrooms 2 Bathrooms Sleeps 6 La Brisa #134883ha
$6,000 - $12,000 per month 28 night min stay
$400 - $500 per night 1 night min stay
$165 per night 1 night min stay
- Villa Nomade, Elegant Truman Annex Condo in Old Town 2 Bedrooms 1 Bathroom Sleeps 4 Truman Annex #158403ha
- Duval Street Luxury Home with Private Pool-Perfect for Family Reunions 5 Bedrooms 4 Bathrooms Sleeps 10 Key West Cuban Club #3013408ha
$5,000 - $7,000 per week 7 night min stay
$7,000 - $150,000 per month 28 night min stay
- Villa Fleur, Elegant Truman Annex Condo in Old Town 2 Bedrooms 1 Bathroom Sleeps 4 Truman Annex #207098ha
$12,600 - $19,500 per month 30-31 night min stay
- Key West Embrace: Charming Condo with Pool and Gorgeous Water Views 4 Bedrooms 3.5 Bathrooms Sleeps 8 Truman Annex #3012173ha
$6,000 - $11,500 per month 28 night min stay
$4,500 - $9,500 per month 28 night min stay
- Located on Key West Golf Course, Newly Decorated & Modern 3 Bedrooms+ 2 Bathrooms Sleeps 8 Key West Golf Club #331171ha
- Old Town Compound: Historic Captain’S House W/Screened Porch & Cottage 5 Bedrooms 4 Bathrooms Sleeps 14 Private Homes, Old Town #3012214ha
- Treasure of the Tropics: 4BR/4BA W/ Pool & Rooftop Terrace in Key West 4 Bedrooms 4 Bathrooms Sleeps 8 Truman Annex #3012172ha
$120 - $142 per night 2 night min stay
$109 - $289 per night 3-5 night min stay
$2,415 per week 7 night min stay
$7,000 - $12,000 per month 28-30 night min stay
$3,000 - $6,000 per month 28 night min stay
$5,000 - $7,500 per month 30 night min stay
- Sunset Grace: Pet Friendly Townhome - 2 Blocks from Duval Street! 3 Bedrooms+ 2.5 Bathrooms Sleeps 8 Truman Annex #3013453ha
- Private Paradise: Old Town Key West Home in Truman Annex with Heated Pool 4 Bedrooms 4 Bathrooms Sleeps 8 Truman Annex #3012171ha
$185 per night 2 night min stay
$179 - $399 per night 3-5 night min stay
$139 - $329 per night 3-5 night min stay
- Key West Luxury Art Deco Style Oceanside Condo with Pool and Beach 2 Bedrooms 2 Bathrooms Sleeps 6 Key West Beach Club #255720ha
- Stay in the Nicest Part of Key West ,Truman Annex 2 Bedrooms 1.5 Bathrooms Sleeps 6 Truman Annex #212518ha
$129 - $319 per night 3-5 night min stay
- Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach 2 Bedrooms 2 Bathrooms Sleeps 6 1800 Atlantic #174733ha
- Tranquil Key West Waterfront Setting Studio 0 Bathrooms Sleeps 0 Key Haven #973858ha
- Key West - Poolside Conch Paradise at Key West Golf Club 2 Bedrooms 1.5 Bathrooms Sleeps 4 Key West Golf Club #164920ha
- Old Town Truman & Duval Townhome 2 Bedrooms 2 Bathrooms Sleeps 4 Windward Park #320640ha
- Private Waterfront Key West Home with Pool 3 Bedrooms 3 Bathrooms Sleeps 6 Sunrise Suites #3002764ha
- Charming Key West Townhome with All the Comforts of Home. 2 Bedrooms 2.5 Bathrooms Sleeps 6 Truman Annex #342727ha
- Tropical and Elegant Key West House 1 Bedroom 1 Bathroom Sleeps 8 Other Key West Properties #339863ha
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.