The Islands of Islamorada Resort, a luxury waterfront property in the Upper Keys, has changed hands again — this time in a $38 million acquisition by Mast Capital and Koch Real Estate Investments. The deal puts 22 private villas and eight hotel suites under new ownership less than two years after the resort sold for $72 million, setting up a high-end reset for one of Islamorada’s biggest hospitality bets.
CoStar News reports that Mast Capital and Koch Real Estate Investments paid $38 million for the resort and plan to relaunch sales and marketing for its 22 waterfront villas. The joint venture bought the property from Frisbie Group, with EOS Hospitality coming in to help optimize resort operations.
The property’s previous ownership group, led by The Wills Companies, bought it from Frisbie Group for $72 million in 2024 and planned to sell the villas individually while maintaining the eight-suite hotel, according to The Real Deal. That strategy is now being revisited under a new ownership team, with villa sales and resort operations again being marketed as a single luxury lifestyle package.
The Resort Is Selling A Keys Lifestyle, Not Just Rooms
The Islands of Islamorada combines 22 oceanside villas with eight hotel suites, direct water access, a private beach and a marina offering boat slips, kayaks, paddleboards and sailboats. The resort also features two oceanfront pools, pickleball courts, playgrounds, a beachfront bar and a fitness center, according to the resort’s official site.
The fully furnished villas have four bedrooms and four full bathrooms, along with three-story layouts, covered waterfront loggias, two-car garages, electric-vehicle hookups and integrated smart-home technology. Prices are being relaunched at $3.8 million, and owners will have the option to place their residences into the resort’s rental program, as detailed by Hotel Business.
New Owners Are Betting On Operations And Villa Sales
CoStar reports that Mast Capital plans targeted improvements to guest rooms and public areas while enhancing the resort’s food-and-beverage program. EOS Hospitality now lists The Islands of Islamorada in its portfolio, describing it as a waterfront resort with villas and suites along a private beach, suggesting that the operational reset is already underway.
The acquisition also expands Mast Capital’s Florida resort holdings, which include Little Palm Island Resort & Spa in the Keys and Saddlebrook Resort in the Tampa Bay area. Mast’s own portfolio materials show a broader focus on hospitality and residential projects, a model that lets the firm pair resort operations with high-end real estate sales.
The $34M Price Gap Is The Deal’s Biggest Plot Twist
The eye-catching part of the transaction is the gap between the 2024 sale price and the latest reported purchase price: $72 million then, $38 million now. The two deals are not necessarily apples-to-apples, but the lower basis gives the new ownership group more room to invest in the property while trying to move the villas into the hands of wealthy second-home buyers.
That bet depends on the same scarcity argument that has fueled luxury development across the Keys. In comments reported by Hotel Management, Mast Chief Investment Officer Jordan Kornberg described the Florida Keys as a supply-constrained hospitality market with high barriers to entry — precisely the kind of market where a rare waterfront property can command attention even after an ownership change.
