OTO Development acquires its first Key West hotel

Best Western Key Ambassador Resort Inn. Photo credit: OTO Development

OTO Development entered the Florida Keys hospitality market with the purchase of the Best Western Key Ambassador Resort Inn. The transaction was completed Sept. 17, between The Key Ambassador Co. and Spartanburg-based OTO, which is part of The Johnson Group.

The buyer's representative was HFF LP (Max Comess and Alexandra Lalos), and the seller's representative was Berkshire Hathaway Knight & Gardner Realty (Claude Gardner and Will Langley).

"We are delighted to add this popular Key West property to our portfolio of owned hotels," Corry Oakes, CEO of OTO Development, said in a statement. "This purchase extends the geographic reach of our operations with an ideal location in America's southernmost city."


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While OTO built its reputation by developing new hotels in high-barrier-to-entry markets, the company's growth strategy also includes purchasing—and repurposing—existing assets in prime locations. The goal is to maximize an acquired property's potential via change processes as simple as operational updates and aesthetic renovations or as complex as a total upfit. For example, OTO recently transformed the O'Callaghan Hotel in downtown Annapolis, Md., into a new Hilton Garden Inn.

Originally built in the 1950s, the 100-room Key Ambassador Resort Inn will undergo a total refresh over the course of the next 12 to 18 months. With each of its seven buildings upfitted one at a time, the property will remain open during renovations. Project partners include general contractor Marino Construction Group and architect Thomas E. Pope. Both companies are local to Key West.  

Jaqueline Loring has been named GM of the Key Ambassador Resort Inn. The longtime OTO employee previously served as GM of a Residence Inn in Florida.

"For decades, the Key Ambassador Resort has been a Key West destination all its own," Loring said in a statement. "It's a privilege to join this property's long-time, loyal staff and I look forward to welcoming visitors to enjoy the lovely ocean views, waterfront pool, Cheekie Hut, even an iguana or two."