Four Seasons Resort and Residences Anguilla assigns each villa guest a dedicated golf cart. The beachfront and blufftop villas spread across Meads Bay and Barnes Bay on Anguilla, a British Overseas Territory in the eastern Caribbean, run from 5,700 to 8,800 square feet and split into oceanview, oceanfront, and beachfront types depending on how close each sits to the water.

Each villa comes with multiple bedrooms, a private pool, a gourmet kitchen, an outdoor shower, and its own host and concierge, who arrange private dining and spa treatments without routing guests through the main resort. The arrangement sits inside the resort’s wider inventory of 181 rooms, suites, residences, townhomes, and villas, more than eighty percent of which already carry a private plunge or infinity pool and a Caribbean Sea view, with multi-bedroom layouts built for families alongside smaller retreats for couples.

Most travelers reach the resort by flying into St. Maarten and crossing the strait by a thirty-minute boat, though direct flights also connect from Miami, Newark, Baltimore, Boston, San Juan, Antigua, and St. Barths. The resort overlooks two of Anguilla’s thirty-three beaches, a small share of an island whose more than one hundred restaurants have earned it a reputation as the Caribbean’s culinary capital.

This past summer, Four Seasons Anguilla folded its programming into the island’s own calendar of traditions. The season opened May 31 with a Local Market Experience on Sunset Lawn, timed to Anguilla Day and stocked with artisanal goods and food from local vendors. Boat Racing Watch Parties ran from June 1 through August 6, tied to the A Class Anguilla Day Premier’s Cup, the race recognized as the island’s national sport, with the resort sponsoring its own entry, the Bush Boyz. The Anguilla Summer Festival closed the run from July 10 through August 9, and the resort backed the Players Troup, a costume group marking its fifteenth year with more than two hundred participants, through an on-property program on mas artistry and costume design. Bookings for the season routed through the resort’s Discover Anguilla offer.