Key West, FL

Key West is a small island city sitting at the southwestern end of the Florida Keys, technically part of Monroe County, Florida, and serving as the county seat. With a year-round population of roughly 25,000 residents, it carries a relaxed, tropical character that feels distinctly different from the mainland, a blend of colorful Conch-republic heritage, fishing-village roots, and a long-standing reputation as a haunt for writers, artists, and travelers. It is best known as the southernmost city in the continental United States and as the western gateway to the Florida Keys, with the only living coral barrier reef in the continental U.S. just offshore. From Miami, Key West lies about 160 miles to the southwest, a drive of roughly three and a half hours along the Overseas Highway, one of the most scenic drives in the country.

About 70 miles west of Key West, accessible by a roughly two-and-a-half-hour ferry ride or a shorter seaplane hop, lies Dry Tortugas National Park. The park covers a small cluster of islands surrounded by turquoise water, with the centerpiece being the massive 19th-century brick fortress Fort Jefferson, one of the largest masonry structures in the Western Hemisphere. Visitors come for the snorkeling, the birdlife, and the sense of remoteness that comes with reaching a place so far from the mainland.

Back in town, Fort Zachary Taylor State Park sits at the western tip of the island, about a ten-minute drive from most of Old Town. It draws visitors for its beach, which is generally regarded as one of the best in Key West, along with shaded picnic areas, nature trails, and a glimpse of the fort itself, built in the mid-1800s as part of the country's coastal defense system. It is a popular spot for both daytime swimming and sunset-watching away from the busier Mallory Square crowds.

A short walk or bike ride from anywhere in Old Town leads to the Ernest Hemingway Home and Museum, where the author lived during the 1930s. The Spanish Colonial house, set on lush grounds, is famous for its population of six-toed cats said to descend from Hemingway's own pet. Just down the street, the bright concrete buoy marking the Southernmost Point in the Continental United States is one of the most photographed spots in town, and the surrounding blocks of restored wooden homes, guesthouses, and small cafés capture the easygoing character that keeps visitors returning year after year.

For short-term rental owners, Key West offers a rare combination: a strong year-round tourism base, a domestic and international visitor pipeline flowing straight down the Overseas Highway, and an island setting where limited land and strict local regulations keep supply constrained. Its marquee attractions, from the sunset crowds and Hemingway lore to the bucket-list day trip to Dry Tortugas, give guests a clear reason to book, while the walkable Old Town, the harbor, and the surrounding state parks make almost any well-located property a compelling home base for exploring the southernmost stretch of the country.