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Best Vacation Rentals in Windward - Holiday Lettings - Cabins
1 Vacation rentals
from $1,145 / night
$8,015 - $23,302 / 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 $526 / night
$3,680 / 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 $184 / night
$1,288 / 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 $135 / night
$945 / week
from $614 / night
$4,294 / week
from $643 / night
$4,500 - $6,500 / week
from $614 / night
$4,294 / week
Vacation apartment with shared pool in Oyster Pond
Oyster Pond apartment
- 1 bedroom
- 1 bathroom
- sleeps 3
from $154 / night
$982 / 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 $526 / night
$3,680 / 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 $500 / night
$3,500 - $6,006 / week
from $500 / night
$3,500 - $6,500 / week
from $350 / night
$2,450 - $6,300 / week
from $2,800 / night
$19,600 - $39,998 / week
from $215 / night
$1,505 - $3,150 / week
from $595 / night
$3,570 - $6,650 / week
from $1,300 / night
$9,100 - $17,535 / week
from $915 / night
$6,400 - $18,000 / week
from $800 / night
$5,600 - $9,499 / week
from $671 / night
$4,700 - $10,000 / week
from $986 / night
$6,900 - $14,500 / 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 $475 / night
$3,325 - $6,650 / week
from $1,143 / night
$8,000 - $25,000 / week
from $429 / night
$3,003 - $5,600 / week
from $515 / night
$3,605 - $7,000 / week
from $315 / night
$2,205 - $5,705 / week
from $503 / night
$3,520 - $6,300 / week
from $1,329 / night
$9,303 - $20,202 / week