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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

$8,217 - $24,443 / week

1 / 24

Great rentals within 20 miles that match your search

Vacation hotel apartment rental

Oyster Pond hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $621 / night

$4,345 / week

1 / 8

Villa rental in Simpson Bay

Simpson Bay villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

from $2,800 / night

$19,600 - $39,998 / week

1 / 69

Vacation home in Orient Bay

Orient Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $700 / night

$4,900 - $10,000 / week

1 / 65

St Martin / St Maarten Vacation villa rental

St Martin / St Maarten villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $490 / night

$3,435 - $11,450 / week

1 / 25

Philipsburg Vacation apartment rental

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $524 / night

$3,664 / week

1 / 12

Vacation apartment in Philipsburg

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $213 / night

$1,490 - $2,011 / week

1 / 33

Vacation villa in Anse de Lorient

Anse de Lorient villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $683 / night

$4,782 - $20,111 / week

1 / 49

Vacation apartment in Philipsburg

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $491 / night

$3,435 / week

1 / 5

Villa rental in Colombier

Colombier villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $705 / night

$4,924 / week

1 / 27

Simpson Bay Vacation villa rental

Simpson Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 17

from $2,072 / night

$14,500 - $28,000 / week

1 / 61

Vacation apartment in Oyster Pond

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $409 / night

$2,863 / week

1 / 19

Vacation condo rental

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $655 / night

$4,580 / week

1 / 30

Vacation apartment in Oyster Pond

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $532 / night

$3,724 / week

1 / 9

Vacation villa in Petit Cul de Sac

Petit Cul de Sac villa

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 6

Pricing unknown

1 / 18

Oyster Pond Vacation condo rental

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $178 / night

$1,242 / week

1 / 32

Apartment rental in Dawn Beach with shared pool

Dawn Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $435 / night

$3,042 / week

1 / 10

Philipsburg Vacation home rental

Philipsburg house

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

from $3,000 / night

$21,000 - $30,660 / week

1 / 69

Philipsburg Vacation villa rental

Philipsburg villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 14

from $3,435 / night

$24,045 / week

1 / 59

Vacation home in Cul de Sac

Cul de Sac house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from $2,000 / night

$14,000 - $28,000 / week

1 / 66

Colombier Vacation villa rental

Colombier villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $565 / night

$3,952 - $5,622 / week

1 / 49

Philipsburg Vacation condo accommodation

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $487 / night

$3,407 / week

1 / 19

Apartment rental in Oyster Pond

Oyster Pond apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

from $149 / night

$974 - $1,575 / week

1 / 12

Vacation villa in Grand Cul-de-Sac

Grand Cul-de-Sac villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

from $609 / night

$4,345 / week

1 / 15

Home rental in Orient Bay

Orient Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $360 / night

$2,520 - $5,880 / week

1 / 26

Vacation villa in St. Jean

St. Jean villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $26,051 / night

$182,355 / week

1 / 12

Vacation villa rental

Simpson Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from $745 / night

$5,210 / week

1 / 36

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 Orient Bay

Orient Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $942 / night

$6,594 - $14,406 / week

1 / 56

Oyster Pond Vacation villa rental

Oyster Pond villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $2,289 / night

$19,236 / week

1 / 28

Orient Bay Vacation villa rental

Orient Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $750 / night

$5,250 - $10,500 / week

1 / 35

Oyster Pond Vacation studio rental

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

from $154 / night

$1,074 / week

1 / 18

Oyster Pond Vacation studio rental

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

from $154 / night

$1,074 / week

1 / 18

Oyster Pond Vacation studio rental

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

from $154 / night

$1,074 / week

1 / 18

Vacation studio with shared pool in Oyster Pond

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

from $154 / night

$1,074 / week

1 / 18

Studio rental in Oyster Pond with shared pool

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

from $154 / night

$1,074 / week

1 / 18

Studio rental in Oyster Pond with shared pool

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

from $154 / night

$1,074 / week

1 / 18

Oyster Pond Vacation studio rental

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

from $154 / night

$1,074 / week

1 / 21

Oyster Pond Vacation studio rental

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

from $154 / night

$1,074 / week

1 / 18

Oyster Pond Vacation studio rental

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

from $154 / night

$1,074 / week

1 / 18