Viewing 40 of 582 rentals in Windward
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Vacation homes - vacation rentals
1 Vacation rentals
from $1,145 / night
$8,015 - $24,328 / week
Great rentals within 20 miles that match your search
from $487 / night
$3,406 / week
from $185 / night
$1,294 / week
from $1,286 / night
$9,000 - $45,000 / week
from $1,929 / night
$13,500 - $35,500 / week
from $808 / night
$5,651 / week
from $100 / night
$699 / week
from $2,429 / night
$17,000 - $35,000 / 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 $524 / night
$3,665 / 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 $739 / night
$4,927 / 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 $1,201 / night
$8,407 / week
from $491 / night
$3,435 / week
from $311 / night
$2,173 / week
from $865 / night
$6,053 / week
from $1,072 / night
$7,504 - $17,800 / week
from $1,875 / night
$9,373 - $23,435 / week
from $138 / night
$916 / week
from $638 / night
$4,466 / week
from $528 / night
$3,696 / week
from $491 / night
$3,435 / week
from $3,571 / night
$25,000 - $42,000 / week
from $935 / night
$6,545 - $14,000 / week
from $500 / night
$3,500 - $6,006 / week
from $2,800 / night
$19,600 - $39,998 / week
from $500 / night
$3,500 - $6,500 / week
from $1,300 / night
$9,100 - $17,535 / week
from $350 / night
$2,450 - $6,300 / week
from $595 / night
$3,570 - $6,650 / week
from $915 / night
$6,400 - $18,000 / week
from $986 / night
$6,900 - $14,500 / week
from $800 / night
$5,600 - $9,499 / 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 $671 / night
$4,700 - $10,000 / week
from $1,143 / night
$8,000 - $25,000 / week