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Casitas at Cheeca Lodge & Spa, Islamorada

GETAWAYS • The Keys 

There’s something about the angle of the spindly palm trees on the beach at the Casitas at Cheeca Lodge & Spa, each bending towards the sea as if caught in a persistent breeze. On this private expanse of white sand beach in Islamorada, about a two-hour drive from Miami, 11 cottages dot a property where meandering paths lead to a lap swimming pool and tennis court, and hammocks dangle lazily between those palms.

If it sounds slightly familiar, it’s because this addendum to Cheeca Lodge — the modern resort that evolved from a storied 1940s-era fishing lodge — was formerly a part of next door neighbor The Moorings Village, Islamorada’s longtime treasured cottage retreat. (To complicate matters, The Moorings still operates today with eight cottages on the property it held onto south of Beach Road.) The acquisition by Cheeca Lodge, which took place in 2020, came with two restaurants across the Overseas Highway: Pierre’s, for a French fine dining spin on Keys cuisine, and the laidback Morada Bay Beach Café — both with sunset views.

At the Casitas, barefoot luxury charm is on order. Guests have exclusive domain over the annex, plus access to all the amenities at Cheeca proper, especially useful when it comes to dining. Up the beach and through a private gate, find three restaurants and two tiki bars. (Butlers also ferry orders to cushioned lounge chairs on the beach.) 

On a recent stay in an oceanfront casita, we walked outside onto our patio every morning to the aquamarine water, spreading out to eternity, with no one else in sight. While South Florida does not lack for spectacular waterfront resorts, few offer that kind of vantage. –Shayne Benowitz

→  Casitas at Cheeca Lodge & Spa (Islamorada) • 81801 Overseas Hwy.