Life sometimes provides second chances.
Two years ago, Coconut Grove, Florida-based real estate development and investment firm Mast Capital sought to buy The Islands of Islamorada Resort in the Florida Keys. Another buyer acquired it instead, but recently the opportunity returned to buy the luxury property.
“We were excited when there was a chance to revisit it and circle back,” said Jordan Kornberg, chief investment officer of Mast Capital, in an interview.
Mast, in partnership with Koch Real Estate Investments, bought the property from an ownership group for $38 million, according to CoStar data. Frisbie Group, which developed and opened the resort in 2020, sold the property in 2024 to Wills Companies and its partners for $72 million, providing seller financing and staying on as a partner.
The Keys has been a favored market for Mast given the constrained supply and high barriers to entry along with its strong occupancy level year-round, Kornberg said. Islamorada, a village in the Keys, has always been a big focus for the company.
The Islands of Islamorada Resort is located in the Upper Keys, 90 minutes outside of Miami. It features 22 private oceanside villas and eight hotel suites, and it offers direct water access.
The property also has two oceanfront swimming pools, a private beach, two pickleball courts, two playgrounds, a beachfront bar and a fitness center. Guests staying there also have access to a private marina with boat slips, paddleboards, kayaks and sailboats.
Mast and Koch plan to relaunch sales and marketing for the resort’s 22 waterfront villas with Ocean Sotheby’s International Realty acting as the sales broker. The villas are fully furnished residences offering four bedrooms and four full bathrooms in a three-story layout. The amenities include covered waterfront loggias, two-car garages with electric vehicle hookups, premium finishes and appliances, integrated smart home technology and concrete block construction built to current hurricane code standards. Prices start at $3.8 million.
The plan is to sell the villas and offer the owners a rental program, Kornberg said.
“It's a pretty unique offering because most townhome or single-family homes in the market can be rented for a 30-day minimum. Some are weekly, but to be able to do nightly rental with a standalone villa of this size is a really unique proposition,” he said.
It should be a great offering for someone who wants more space and high-quality new build improvements, he said. It also means owners can generate good cash flow through the nightly rentals.
There will be some targeted improvements to the rooms and public areas along with enhancing the food and beverage program, he said. Along with the focus on the villa sales, the company is bringing in Eos Hospitality to optimize the resort’s operations.
Mast’s portfolio has about $5 billion in total capitalization, primarily in residential hospitality across the state of Florida, he said. Among its hospitality properties are the Little Palm Island Resort & Spa, also in the Keys, and the recently renovated Saddlebrook Resort in Tampa Bay.
The company has residential projects in the works, including luxury oceanfront condominium The Perigon Miami Beach, which it is developing with Starwood Capital Group, as well as the 80-story luxury residential tower Cipriani Residences Miami in the Brickell neighborhood and the Banyan Tree Residences West Palm Beach, Banyan Group’s first residential project in the U.S.