Underwater Cabana at Custom House Inn

The below-street-level cabana at Custom House Inn, tucked into 124 Duval Street, positions guests at the heart of Key West's Old Town — the historic Custom House museum stands less than a block north, and the nightly Mallory Square sunset celebration is a seven-minute walk west.

The unit's sunken layout gives it the feel of a private garden apartment rather than a standard inn room, with natural light filtered through ground-level foliage. Duval Street's bar strip is immediately outside, making this one of the few addresses where guests can walk home in under sixty seconds.

Key West's Conch Train and water taxi depart within three blocks, and the Florida Keys Overseas Highway connects to Miami in roughly three and a half hours.