History of Pearl's Rainbow

The main building at Pearl’s Rainbow was originally a Marrero cigar factory built in the late 1800’s.  A recent 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.  

“I want the owners to know they have done a beautiful job expanding and remodeling the resort.”

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 has been a guesthouse for women since 1989, and became Pearl’s Rainbow in 2000. 

"I have been here several times and each time is more enjoyable than the last.  Thanks for your excellent
customer service!”

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.