Viewing 40 of 1,122 rentals in Windward
Tell us your dates, and we will find the most accurate rates and availability for you
Updating
Best Vacation Rentals in Windward - Holiday Lettings - Cabins
1 Vacation rentals
from $1,145 / night
$8,015 - $23,677 / 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 $135 / night
$945 / week
from $614 / night
$4,296 / week
from $643 / night
$4,500 - $6,500 / week
from $614 / night
$4,296 / week
Vacation apartment with shared pool in Oyster Pond
Oyster Pond apartment
- 1 bedroom
- 1 bathroom
- sleeps 3
from $154 / night
$982 / 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
$3,682 / week
from $655 / night
$4,580 / week
from $522 / night
$3,651 / 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 $74 / night
$516 / 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
Vacation apartment with shared pool in Oyster Pond
Oyster Pond apartment
- 3 bedrooms
- 2 bathrooms
- sleeps 8
from $573 / night
$4,008 / week
from $1,197 / night
$8,376 / week
from $491 / night
$3,435 / week
from $862 / night
$6,031 / 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 $1,868 / night
$9,338 - $23,349 / week
from $138 / night
$916 / week
from $327 / night
$1,713 - $2,194 / week
from $166 / night
$1,140 / week
from $526 / night
$3,682 / week
from $1,374 / night
$9,618 / week
from $201 / night
$1,374 - $1,718 / week
from $526 / night
$3,682 / week
from $605 / night
$4,234 / week
from $982 / night
$6,870 / week
from $491 / night
$3,435 / week
from $295 / night
$2,061 / week
from $458 / night
$3,206 / week
from $172 / night
$1,203 / week
from $485 / night
$3,394 / week
from $184 / night
$1,289 / week
from $614 / night
$4,294 / week
from $526 / night
$3,682 / 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
$1,289 / week