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"Founded by Jane Street Capital cofounder Tim Reynolds, these ultra-luxury properties pair high-end, personalized hospitality with a philanthropic mission that supports nearby art academies. The villas and resorts offer sophisticated open-air settings, one-to-one staff service, multi-course meals by top chefs and playful, high-quality amenities (including sleek waterslides that drop into infinity pools). Guests can book immersive activities such as scuba diving, snorkeling, paddleboarding, kayaking or fully catered beach barbecues, and the properties intentionally commission and hire local artists as part of community engagement. Reservations require full buyouts (minimum five nights) and command premium rates (starting around $15,000 per night, roughly $750 per guest), while aiming to feel unstuffy and highly personal; the founder, who studied the Waichulis technique after a 2000 car crash left him paralyzed from the waist down, also converted private cliffside homes (for example on Anguilla’s Little Bay) into bookable villas." - Laura Dannen Redman
Ultra-luxury villas with private pools, chef-prepared meals, & attentive staff
2640, Little Bay 2640, Anguilla Get directions