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Vacation homes - vacation rentals

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Windward Vacation villa rental

Pointe Milou villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from $1,145 / night

$8,015 - $23,447 / week

1 / 24

Great rentals within 20 miles that match your search

Vacation condo with shared pool in Pointe Blanche

Pointe Blanche condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $265 / night

$1,855 - $4,025 / week

1 / 15

Vacation villa in Cole Bay

Cole Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $644 / night

$4,508 - $14,798 / week

1 / 41

Vacation villa in Grand Cul-de-Sac

Grand Cul-de-Sac villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

from $600 / night

$4,280 / week

1 / 15

Orient Bay Vacation home rental

Orient Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $263 / night

$1,841 - $3,360 / week

1 / 22

Vacation villa in St. Jean

St. Jean villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $25,552 / night

$178,861 / week

1 / 12

Oyster Pond Vacation apartment rental

Oyster Pond apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $321 / night

$2,245 / week

1 / 23

Vacation condo with shared pool in Oyster Pond

Oyster Pond condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from $516 / night

$3,607 / week

1 / 24

Vacation villa with swimming pool in Cul de Sac

Cul de Sac villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 11

from $972 / night

$6,804 - $17,500 / week

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Oyster Pond Vacation villa accommodation

Oyster Pond villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $499 / night

$3,490 - $4,550 / week

1 / 17

Vacation villa in Oyster Pond

Oyster Pond villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $659 / night

$4,609 / week

1 / 39

Vacation condo in Oyster Pond

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $327 / night

$2,285 / week

1 / 6

Cul de Sac Vacation villa rental

Cul de Sac villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,000 / night

$7,000 - $14,000 / week

1 / 56

Villa rental in Oyster Pond with swimming pool

Oyster Pond villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

from $613 / night

$4,290 - $9,002 / week

1 / 49

Orient Bay Vacation apartment rental

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $120 / night

$840 - $1,680 / week

1 / 13

Philipsburg Vacation home rental

Philipsburg house

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

from $3,000 / night

$21,000 - $30,660 / week

1 / 69

Orient Bay Vacation apartment rental

Orient Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $252 / night

$1,764 - $3,042 / week

1 / 18

Villa accommodation in Philipsburg

Philipsburg villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,946 / night

$13,618 / week

1 / 12

Vacation home with swimming pool in Orient Bay

Orient Bay house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from $189 / night

$1,323 - $2,401 / week

1 / 21

Home rental in Orient Bay

Orient Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $360 / night

$2,520 - $5,880 / week

1 / 38

Vacation home with swimming pool in Orient Bay

Orient Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $360 / night

$2,520 - $5,400 / week

1 / 38

Vacation villa with swimming pool in Vitet

Vitet villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $500 / night

$3,500 - $12,000 / week

1 / 21

Vacation villa in Cul de Sac

Cul de Sac villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $637 / night

$4,458 / week

1 / 56

Vacation studio in Cul de Sac

Cul de Sac studio

  • Studio
  • 1 bathroom
  • sleeps 4

from $151 / night

$755 - $1,278 / week

1 / 16

Vacation villa rental

Cul de Sac villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $711 / night

$4,973 / week

1 / 52

Cul de Sac Vacation villa rental

Cul de Sac villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from $576 / night

$4,030 / week

1 / 48

Vacation villa rental

Cul de Sac villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from $515 / night

$3,601 / week

1 / 40

Vacation villa with swimming pool, golf nearby in Orient Bay

Orient Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

from $261 / night

$1,886 - $2,941 / week

1 / 27

Orient Bay Vacation villa rental

Orient Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $258 / night

$1,801 / week

1 / 28

Vacation villa with swimming pool in Orient Bay

Orient Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 16

from $626 / night

$4,382 / week

1 / 33

Vacation villa in Oyster Pond

Oyster Pond villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $643 / night

$4,500 - $6,500 / week

1 / 25

Vacation villa rental

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $808 / night

$5,651 / week

1 / 32

Vacation hotel apartment in Dawn Beach

Dawn Beach hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $522 / night

$3,651 / week

1 / 11

Condo rental in Orient Bay

Orient Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $74 / night

$516 / week

1 / 9

Vacation villa rental

Marigot, Saint Martin villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from $737 / night

$4,909 / week

1 / 35

Vacation condo in Dawn Beach

Dawn Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $491 / night

$3,435 / week

1 / 19

Orient Bay Vacation home rental

Orient Bay house

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

from $310 / night

$2,165 / week

1 / 44

Vacation apartment rental

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $862 / night

$6,031 / week

1 / 46

Vacation villa with swimming pool in Gustavia

Gustavia villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,868 / night

$9,338 - $23,349 / week

1 / 37

Vacation studio with shared pool in Orient Bay

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 3

from $138 / night

$916 / week

1 / 31