Viewing 40 of 758 rentals in Windward
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Vacation homes - vacation rentals
1 Vacation rentals
from $1,145 / night
$8,015 - $23,884 / week
Great rentals within 20 miles that match your search
from $885 / night
$6,195 - $14,980 / week
from $231 / night
$1,581 / week
from $264 / night
$1,844 / week
from $250 / night
$1,750 - $2,500 / week
from $334 / night
$2,333 / week
from $103 / night
$716 / week
from $311 / night
$2,171 / week
Apartment rental in Dutch Cul de Sac with shared pool
Dutch Cul de Sac apartment
- 2 bedrooms
- 3 bathrooms
- sleeps 5
from $395 / night
$2,919 - $7,115 / week
from $211 / night
$1,476 / week
from $1,603 / night
$11,221 - $16,030 / week
from $500 / night
$3,500 - $12,000 / week
from $458 / night
$3,200 - $33,500 / week
Vacation apartment with shared pool in Orient Bay
Orient Bay apartment
- 1 bedroom
- 1 bathroom
- sleeps 2
from $153 / night
$1,067 / week
from $415 / night
$2,901 / week
from $598 / night
$4,181 / week
Vacation apartment with shared pool in Oyster Pond
Oyster Pond apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 6
from $516 / night
$3,607 / week
from $611 / night
$4,274 / week
from $643 / night
$4,500 - $6,500 / week
from $808 / night
$5,651 / week
Vacation apartment with shared pool in Oyster Pond
Oyster Pond apartment
- 1 bedroom
- 1 bathroom
- sleeps 3
from $153 / night
$977 / week
from $100 / night
$699 / week
Vacation hotel apartment with shared pool in Oyster Pond
Oyster Pond hotel apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 8
from $524 / night
$3,663 / week
from $3,571 / night
$25,000 - $42,000 / week
from $935 / night
$6,545 - $14,000 / week
Vacation apartment with shared pool in Orient Bay
Orient Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
from $310 / night
$2,170 - $4,270 / week
Vacation apartment with swimming pool in Orient Bay
Orient Bay apartment
- 2 bedrooms
- 3 bathrooms
- sleeps 6
from $225 / night
$1,575 - $3,360 / week
from $2,800 / night
$19,600 - $39,998 / week
from $500 / night
$3,500 - $6,006 / week
from $500 / night
$3,500 - $6,500 / week
from $350 / night
$2,450 - $6,300 / week
from $1,300 / night
$9,100 - $17,535 / week
Vacation apartment with shared pool in Simpson Bay
Simpson Bay apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
from $229 / night
$1,600 - $3,500 / week
from $215 / night
$1,505 - $3,150 / week
from $595 / night
$3,570 - $6,650 / week
from $986 / night
$6,900 - $14,500 / week
from $671 / night
$4,700 - $10,000 / week
from $475 / night
$3,325 - $6,650 / week
from $515 / night
$3,605 - $7,000 / week
from $797 / night
$5,579 - $10,178 / week