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Luxury rentals in Leeward Settlement

Find and book unique accommodations on Airbnb

Top-rated luxury vacation rentals in Leeward Settlement

Guests agree: these stays are highly rated for location, cleanliness, and more.

Saving Grace
LUXE
Entire villa · 8 guests · 6 beds · 3.5 baths

Saving GracePlantation style villa on the beach

Footprints on the Beach
LUXE
Entire villa · 12 guests · 6 beds · 6 baths

Footprints on the BeachFootprints on the Beach

Hawksbill
LUXE
Entire villa · 16 guests · 8 beds · 8.5 baths

HawksbillContemporary Caribbean villa on the beach

Luxury rentals for every style

The right home for your next dream getaway

  • Featured Homes
  • Flexible bookings
  • Ready to book homes

Popular amenities for Leeward Settlement luxury vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning
  • Gated property

Other great luxury vacation rentals in Leeward Settlement

LUXEEntire villa
Milestone
$2,650 / night
LUXEEntire villa
Aqueous
$1,250 / night
LUXEEntire villa
Big Chill Villa
$2,257 / night
LUXEEntire villa
Villa Awa
$6,900 / night
LUXEEntire villa
Villa Del Sol
$1,950 / night
LUXEEntire villa
Beach House at Hawksbill
$2,300 / night
LUXEEntire villa
Edge of Paradise
$950 / night
LUXEEntire villa
Second Chances
$2,520 / night
LUXEEntire villa
Sentosa
$15,000 / night
LUXEEntire villa
Pelican Vista
$1,810 / night
LUXEEntire villa
Villa Viatu
$1,945 / night
LUXEEntire villa
Vision Beach
$9,000 / night