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DESTINATION

Leeward Settlement

Start-to-finish trip planning
Concierge teams coordinate your arrival, departure, and everything in between.
300+ point inspection
Every Luxury Retreats home is personally verified to be in pristine condition.
On-trip care, 24/7
Premium, on-demand assistance for any question, at any time of day.

86 luxury villas and vacation rentals in Leeward Settlement

1 18 of 86 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added. Free cancellation only applicable within 48 hours from booking.
Exceptional Quality
Crafting exceptional experiences in the world's most memorable places
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