Viewing 40 of 1,126 rentals in Windward
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Best Vacation Rentals in Windward - Holiday Lettings - Cabins
1 Vacation rentals
from $1,145 / night
$8,015 - $23,907 / week
Great rentals within 20 miles that match your search
Vacation apartment with shared pool in Oyster Pond
Oyster Pond apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 6
from $516 / night
$3,607 / week
from $614 / night
$4,294 / week
from $522 / night
$3,649 / week
Apartment rental in Oyster Pond with shared pool
Oyster Pond apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 8
from $401 / night
$2,806 / week
from $183 / night
$1,277 / week
from $1,286 / night
$9,000 - $45,000 / week
from $1,929 / night
$13,500 - $35,500 / week
Vacation apartment with shared pool in Orient Bay
Orient Bay apartment
- 1 bedroom
- 1 bathroom
- sleeps 2
from $149 / night
$985 / week
from $134 / night
$937 / week
from $608 / night
$4,257 / week
from $643 / night
$4,500 - $6,500 / week
from $608 / night
$4,257 / week
Vacation apartment with shared pool in Oyster Pond
Oyster Pond apartment
- 1 bedroom
- 1 bathroom
- sleeps 3
from $152 / night
$973 / week
from $100 / night
$699 / week
from $491 / night
$3,435 / week
Vacation hotel apartment with shared pool in Oyster Pond
Oyster Pond hotel apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 8
from $522 / night
$3,649 / week
from $371 / night
$1,691 - $6,799 / week
from $869 / night
$6,081 / week
from $409 / night
$2,863 / week
Vacation villa with swimming pool, golf nearby in Philipsburg
Philipsburg villa
- 3 bedrooms
- 3 bathrooms
- sleeps 6
from $401 / night
$2,806 / week
from $655 / night
$4,580 / week
from $517 / night
$3,619 / week
from $434 / night
$3,035 / week
Penthouse rental in Oyster Pond with shared pool
Oyster Pond penthouse
- 3 bedrooms
- 2 bathrooms
- sleeps 8
from $490 / night
$3,430 / week
from $73 / night
$511 / week
Vacation apartment with shared pool in Cul de Sac
Cul de Sac apartment
- 2 bedrooms
- 3 bathrooms
- sleeps 5
from $298 / night
$2,061 / week
from $730 / night
$4,865 / week
Vacation apartment with shared pool in Oyster Pond
Oyster Pond apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 8
from $573 / night
$4,008 / week
from $1,186 / night
$8,301 / week
from $491 / night
$3,435 / week
from $854 / night
$5,977 / week
from $1,072 / night
$7,504 - $17,800 / week
Apartment rental in Simpson Bay with shared pool
Simpson Bay apartment
- 1 bedroom
- 1 bathroom
- sleeps 5
from $315 / night
$1,941 / week
from $138 / night
$916 / week
from $327 / night
$1,713 - $2,194 / week
from $166 / night
$1,140 / week
from $521 / night
$3,649 / week
from $1,374 / night
$9,618 / week
from $201 / night
$1,374 - $1,718 / week