Viewing 40 of 675 rentals in Windward
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Vacation homes - vacation rentals
1 Vacation rentals
from $1,145 / night
$8,015 - $23,725 / week
Great rentals within 20 miles that match your search
from $295 / night
$2,061 / week
from $458 / night
$3,206 / week
from $482 / night
$3,374 / week
from $183 / night
$1,282 / 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 $183 / night
$1,282 / week
from $135 / night
$940 / week
from $611 / night
$4,271 / week
from $643 / night
$4,500 - $6,500 / 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 $523 / night
$3,661 / week
from $705 / night
$4,924 / week
from $2,429 / night
$17,000 - $35,000 / week
from $373 / night
$1,696 - $6,821 / week
from $872 / night
$6,101 / 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 $519 / night
$3,630 / 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
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
from $733 / night
$4,881 / 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 $1,190 / night
$8,328 / week
from $491 / night
$3,435 / week
from $857 / night
$5,996 / week
from $1,072 / night
$7,504 - $17,800 / 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 $138 / night
$916 / week
from $327 / night
$1,713 - $2,194 / week
from $166 / night
$1,140 / week
from $523 / night
$3,661 / week
from $1,374 / night
$9,618 / week
from $201 / night
$1,374 - $1,718 / week
from $523 / night
$3,661 / week
from $602 / night
$4,210 / week
from $491 / night
$3,435 / week