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Island length26 km east to west
Named beaches33
Rate range$8,000 to $95,000 / wk
Last updated2026-05
Anguilla is the rare Caribbean island where the villa decision is not whether the beach is good (they all are) but which beach matches the trip. The island has held a low-rise development policy for decades, with no building exceeding the tallest palm on the parcel, and the result is the most coherent villa-first stock in the northern Leewards. The trade-off is no large resort cluster, no built shopping strip, and a working population (roughly 15,800 according to the 2021 census) that runs the trip on its own time.
Most luxury bookings transit Princess Juliana International (SXM) on St Martin, not the small Clayton J Lloyd (AXA) on Anguilla. The 25-minute ferry from Marigot to Blowing Point handles the crossing, with the private charter operators (notably Funtime and Calypso Charters) running on a fixed schedule and on demand. The door-to-door from a US east-coast flight is 5 to 7 hours. From the UK it is 9 to 12 hours via Antigua or St Lucia.
The villa map splits five ways: the western tip (the Cap Juluca and Maundays Bay zone), the south coast (Rendezvous, Cove, Blowing Point), the north-west (Meads Bay, Barnes Bay, Long Bay), the north-east (Shoal Bay East, Island Harbour), and the inland bluffs above. The rate bands differ. The rhythm differs. The right answer depends on the trip.