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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

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

HawksbillContemporary Caribbean villa on the beach

Milestone
LUXE
Entire villa · 8 guests · 6 beds · 4 baths

MilestoneContemporary villa on Grace Bay 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 villaRating 5 out of 5; 4 reviews
Aqueous
R17,520 / night
LUXEEntire villaRating 5 out of 5; 4 reviews
Big Chill Villa
R29,796 / night
LUXEEntire villaRating 5 out of 5; 4 reviews
Villa Awa
R102,798 / night
LUXEEntire villaRating 4.67 out of 5; 6 reviews
Villa Del Sol
R29,052 / night
LUXEEntire villaRating 5 out of 5; 3 reviews
Beach House at Hawksbill
R31,286 / night
LUXEEntire villaRating 4.67 out of 5; 3 reviews
Edge of Paradise
R14,183 / night
LUXEEntire villa
Second Chances
R32,538 / night
LUXEEntire villa
Sentosa
R201,126 / night
LUXEEntire villa
Seagrace
R21,424 / night
LUXEEntire villa
Hawksbill Estate
R269,658 / night
LUXEEntire villa
Cabuya
R78,961 / night
LUXEEntire villa
Pelican Vista
R26,966 / night