Curated · one person's picks, labeled as such

Hemingway's Key West

Old Town homes inside the six blocks Hemingway walked: Duval, Whitehead, the lighthouse, the house with the cats.

A
Adam Norko
Curator

The rule: the listing puts you in Old Town or names the landmarks. Not a ranking, and not every conch house in town.

Hemingway lived on Whitehead Street from 1931 to 1939 and wrote a good part of his best work in the studio over the carriage house. The neighborhood around it is still the neighborhood: gingerbread trim, porch swings, a lighthouse across the street, Duval two blocks over and loud.

Seven homes from two managers with their own booking sites. One names the Hemingway Home directly; the rest qualify on Old Town and Duval, which is the same six blocks. Each links to the manager; you book with them.

Browse here7 homes, 2 management companies, one reason to be on the same page.
Book with the managerEvery link goes to the company's own booking site. Prices, photos, and availability live there.
Or send your dates"Check dates" forwards your dates and party size to the manager and opens their page.

The homes

Last Key RealtyPreview from Last Key Realty's listing

Dreamsicle by Duval

Key West, FL · Last Key Realty
Sleeps 84 BR
Listing: Duval Street is a few steps away, as are the Ernest Hemingway House and the Key West Lighthouse.
See the home
Found on Last Key Realty's site. Facts per the listing, September 2026.
Last Key RealtyPreview from Last Key Realty's listing

Top of Old Town

Key West, FL · Last Key Realty
Sleeps 62 BR
Listing: perched above the sights and sounds of Duval Street, in the heart of Old Town.
See the home
Found on Last Key Realty's site. Facts per the listing, September 2026.
Last Key Realty

Memoir Manor

Key West, FL · Last Key Realty
Sleeps 63 BR
Listing: a quiet corner of Old Town within easy reach of Duval Street and Mallory Square.
See the home
Found on Last Key Realty's site. Facts per the listing, September 2026.
Last Key Realty

The Toasted Coconut

Key West, FL · Last Key Realty
Sleeps 83 BR
Listing: classic Key West architecture, gingerbread trim and a porch swing, the vocabulary of Old Town conch homes.
See the home
Found on Last Key Realty's site. Facts per the listing, September 2026.
Rent Key West Vacations

Ole' Olivia

Key West, FL · Rent Key West Vacations
Sleeps 84 BR
Listing: in the heart of Old Town, two blocks to Duval Street.
See the home
Found on Rent Key West Vacations's site. Facts per the listing, September 2026.
Rent Key West Vacations

Casa Caribe

Key West, FL · Rent Key West Vacations
Sleeps 84 BR
Listing: steps from upper Duval and the Southernmost Point, walking distance to lower Duval.
See the home
Found on Rent Key West Vacations's site. Facts per the listing, September 2026.
Rent Key West Vacations

Louisa House

Key West, FL · Rent Key West Vacations
Sleeps 104 BR
Listing: half a block off Duval, walking distance to the Atlantic beaches and the Southernmost Point.
See the home
Found on Rent Key West Vacations's site. Facts per the listing, September 2026.
The house itself

The Hemingway Home and Museum on Whitehead Street is open daily; the cats are real and there are a lot of them.

  • The Ernest Hemingway Home and Museum, 907 Whitehead St, Key West: source, museum