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Luxury rentals in Leeward Settlement

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Top-rated luxury vacation rentals in Leeward Settlement

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

LUXE
  1. Entire villa
  2. Grace Bay
Amazing Grace · Neoclassical villa on 600 feet of white sandy beach

Neoclassical villa on 600 feet of white sandy beach

ﺩ.ﺇ24,531 per night
LUXE
  1. Entire villa
  2. Grace Bay
Saving Grace · Plantation style villa on the beach

Plantation style villa on the beach

ﺩ.ﺇ17,263 per night
LUXE
Professionally inspected
  1. Entire villa
  2. Grace Bay
The Tuscany · The Tuscany - 3Br - Sleeps 6. Lower rates for fewer bedrooms may be available upon request.

The Tuscany - 3Br - Sleeps 6. Lower rates for fewer bedrooms may be available upon request.

ﺩ.ﺇ7,530 per night

Luxury rentals for every style

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Popular amenities for Leeward Settlement luxury vacation rentals

Other great luxury vacation rentals in Leeward Settlement

LUXE
  1. Entire villa
  2. Grace Bay
Coral House · Classical revival villa on the beach
ﺩ.ﺇ33,057 per night
LUXE
  1. Entire villa
  2. The Bight
Villa Islander · Tropical Brutalist architecture near the beach
ﺩ.ﺇ11,570 per night
LUXE
  1. Entire villa
  2. The Bight Settlement
Turtle Ridge Villa · Tropical postmodernism near Grace Bay Beach
ﺩ.ﺇ7,342 per night
LUXE
  1. Entire villa
  2. Grace Bay
Turquoise Villa · Sleek modern villa near Grace Bay Beach
ﺩ.ﺇ6,611 per night
LUXE
  1. Entire villa
  2. Grace Bay
Hawksbill · Contemporary Caribbean villa on the beach
ﺩ.ﺇ55,096 per night
LUXE
  1. Entire villa
  2. Grace Bay
Milestone · Contemporary villa on Grace Bay Beach
ﺩ.ﺇ9,734 per night
LUXE
  1. Entire villa
  2. Leeward Settlement
Sugar Apple
ﺩ.ﺇ4,775 per night
LUXE
  1. Entire villa
  2. Grace Bay
Villa Awa · Neomodern beachfront villa on Grace Bay
ﺩ.ﺇ29,384 per night
LUXE
  1. Entire villa
  2. Grace Bay
Coral Pavilion · Neoclassical Villa on a Caribbean beach
ﺩ.ﺇ28,282 per night
LUXE
  1. Entire villa
  2. Leeward Settlement
Seagrace
ﺩ.ﺇ4,591 per night
LUXE
  1. Entire villa
  2. Grace Bay
Beach House at Hawksbill · Contemporary craft villa on the Caribbean
ﺩ.ﺇ9,917 per night
LUXE
  1. Entire villa
  2. The Bight Settlement
Casa Grande · Beach retreat in Grace Bay, Turks and Caicos
ﺩ.ﺇ13,223 per night