Named for landscape painter Winslow Homer, who wintered in Key West around the turn of the 19th century, this is the largest hotel in the Kimpton Key West collection comprised from multiple historic homes that make no guest room designed the same. Wander down brick walkways through vibrant greenery, stopping to play a game of corn hole or snap a photo at our “Instagram Tree”—all on grounds that were once covered in fruit groves. Today, wedding parties, families and couples enjoy coveted moments of relaxation and play in a central Old Key West locale.

Winslow's Bungalows spans a lush, landscaped campus in the heart of Old Town. Named for famous painter and summer resident Winslow Homer, this expansive haven boasts three private pools, an outdoor bar and vibrant gardens. It’s an idyllic scene for couples, families, groups and wedding parties.

With 85 guestrooms including two deluxe suites, Winslow's Bungalows is our largest Key West hotel. This expansive haven extends across several historic Key West architectural styles, with an array of past owners including an army officer, an Irish steamboat captain and a circus performer. The colorful backstory is matched by the artful, bohemian interiors and elegant touches like summer cane beds, European armoires and maritime basket lighting.