The Island Hour

A palm-lined compound in the heart of Old Town Key West, this house splits across a main home and a self-contained cottage – each with its own heated plunge pool, making it easy for groups who want to share a trip without living on top of each other. The covered outdoor area opens fully to the living space via sliding glass walls, blurring the line between inside and out, while a garden path leads to an outdoor shower wrapped in tropical planting. Mallory Square's nightly sunset spectacle is an eight-minute walk, Duval Street seven, and the Hemingway Home roughly ten.

Home truths:
* This home comprises a main residence and a separate guesthouse. The guesthouse has its own entrance, two en-suite bedrooms, a kitchenette, living area, workspace, and private plunge pool, making it ideal for guests who prefer a little extra privacy.
* The front porch faces the street and makes a great spot for afternoon people-watching, as guests who've stayed here have noted. Bear in mind that a home this close to the action means foot traffic outside is part of the atmosphere.
* For those with reduced mobility, there's a ground floor bedroom and bathroom here.
* One well-behaved pet 25lbs or less is welcome to accompany you during your stay.
* Due to this home's location, we recommend hiring a car to get the most out of your stay. There's free parking for up to two cars on the driveway.