Viewing 40 of 519 rentals in Windward
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Vacation homes - vacation rentals
1 Vacation rentals
from $1,145 / night
$8,015 - $23,447 / week
Great rentals within 20 miles that match your search
from $613 / night
$4,290 - $9,002 / week
from $551 / night
$3,852 / week
from $92 / night
$685 / week
from $227 / night
$1,589 - $1,925 / week
from $205 / night
$1,432 / week
from $1,700 / night
$11,900 - $28,400 / week
from $864 / night
$6,048 / week
from $640 / night
$4,480 - $9,520 / week
from $750 / night
$5,250 - $10,500 / week
from $344 / night
$2,405 / week
from $857 / night
$6,000 - $10,000 / week
from $344 / night
$2,405 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
from $154 / night
$1,074 / week
Vacation villa in Upper Prince's Quarter
Upper Prince's Quarter villa
- 3 bedrooms
- 2 bathrooms
- sleeps 6
from $629 / night
$4,400 - $7,000 / week
from $885 / night
$6,195 - $14,980 / week
from $212 / night
$1,483 - $1,603 / week
from $1,946 / night
$13,618 / week
from $234 / night
$1,638 - $3,150 / week
from $350 / night
$2,450 - $4,200 / week
from $475 / night
$3,325 - $6,300 / week
from $2,100 / night
$14,700 - $35,000 / week
from $286 / night
$2,000 - $3,500 / week
from $2,100 / night
$14,700 - $35,000 / week
Vacation apartment with shared pool in Orient Bay
Orient Bay apartment
- 1 bedroom
- 1 bathroom
- sleeps 2
from $153 / night
$1,070 / week
from $313 / night
$2,186 / week