Just two blocks from the southernmost point in the continental United States, Pearl’s offers guesthouse ambience and resort amenities in a collection of historic, renovated buildings set amid tropical landscaping.

The main building at Pearl’s Rainbow was originally a Marrero cigar factory built in the late 1800’s. An award-winning renovation restored a series of tobacco-sorters’ bay windows that were once a common feature of wood-frame cigar factories in the Keys. Pearl’s is the only place in Key West where you can find this architectural element today.

The Marrero building was converted to dwelling space after the cigar industry left Key West, and had a surprisingly large number of women owners over the years. Like many places in Key West, there’s a legend that “Hemingway slept here” when it was a boarding house. It was a guesthouse for women beginning in 1989, and became Pearl’s Rainbow in 2000.

Smaller buildings on the property – aptly named the Louisa, East and West Cottages – once served as houses for cigar factory workers. Our youngest structure was built in 1950 as The Surf Motel and served time as a men’s guesthouse (The Pines) before it became part of Pearl’s in the late 1990’s.

The collection of buildings makes Pearl’s Rainbow among the largest guesthouses in Key West, and reflects the variety of the island’s history.

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