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Estates in Windward and Apartments - Holiday Lettings - Holiday Rentals Windward

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Windward holiday villa rental

Pointe Milou villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £916 / night

£6,412 - £19,325 / week

1 / 24

Great rentals within 20 miles that match your search

Simpson Bay holiday villa rental

Simpson Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 17

from £1,944 / night

£13,600 - £27,999 / week

1 / 61

Holiday home in Orient Bay

Orient Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £560 / night

£3,920 - £8,000 / week

1 / 65

St Martin / St Maarten holiday villa rental

St Martin / St Maarten villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £392 / night

£2,748 - £9,160 / week

1 / 25

Holiday villa in Anse de Lorient

Anse de Lorient villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £543 / night

£3,795 - £15,964 / week

1 / 49

Villa rental in Colombier

Colombier villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £564 / night

£3,939 / week

1 / 27

Holiday villa in Petit Cul de Sac

Petit Cul de Sac villa

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 6

Pricing unknown

1 / 18

Colombier holiday villa let

Colombier villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £452 / night

£3,161 / week

1 / 49

Holiday villa in Grand Cul-de-Sac

Grand Cul-de-Sac villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

from £483 / night

£3,449 / week

1 / 15

Holiday villa in St. Jean

St. Jean villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £20,610 / night

£144,270 / week

1 / 12

Holiday villa rental

Simpson Bay villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £596 / night

£4,168 / week

1 / 36

Holiday condo with shared pool in Oyster Pond

Oyster Pond condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from £413 / night

£2,886 / week

1 / 24

Philipsburg holiday home rental

Philipsburg house

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

from £2,160 / night

£15,120 - £24,528 / week

1 / 69

Philipsburg holiday villa rental

Philipsburg villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 14

from £2,748 / night

£19,236 / week

1 / 59

Oyster Pond holiday villa rental

Oyster Pond villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £1,831 / night

£15,389 / week

1 / 28

Holiday villa in Anse des Cayes

Anse des Cayes villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,566 / night

£20,582 / week

1 / 32

Holiday villa with swimming pool in Orient Bay

Orient Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £754 / night

£5,275 - £11,525 / week

1 / 56

Orient Bay holiday villa rental

Orient Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £600 / night

£4,200 - £8,400 / week

1 / 35

Home rental in Orient Bay

Orient Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £288 / night

£2,016 - £4,704 / week

1 / 38

Orient Bay holiday villa rental

Orient Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £638 / night

£4,461 - £11,984 / week

1 / 55

Villa rental in Simpson Bay

Simpson Bay villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

from £2,240 / night

£15,680 - £31,998 / week

1 / 69

Holiday villa rental

Colombier villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £2,286 / night

£16,000 - £48,719 / week

1 / 23

Holiday home in Cul de Sac

Cul de Sac house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,600 / night

£11,200 - £22,400 / week

1 / 66

Holiday villa in Gustavia

Gustavia villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,577 / night

£11,036 - £48,282 / week

1 / 73

St. Jean holiday villa rental

St. Jean villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £936 / night

£6,553 / week

1 / 14

Villa letting in Corossol

Corossol villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £685 / night

£4,791 - £19,960 / week

1 / 99

Anse de Lorient holiday villa rental

Anse de Lorient villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £7,984 / night

£55,887 - £159,677 / week

1 / 100

Holiday villa rental

Lurin villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £1,140 / night

£7,984 - £39,920 / week

1 / 99

Holiday villa in St. Barthelemy

St. Barthelemy villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £559 / night

£3,912 - £15,170 / week

1 / 100

Holiday villa in St. Jean

St. Jean villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £9,439 / night

£66,070 - £159,837 / week

1 / 100

Holiday villa in Petit Cul de Sac

Petit Cul de Sac villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £570 / night

£3,992 - £17,166 / week

1 / 99

Grand Fond holiday villa rental

Grand Fond villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £570 / night

£3,992 / week

1 / 72

Anse des Cayes holiday villa rental

Anse des Cayes villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £411 / night

£2,875 - £15,170 / week

1 / 100

Holiday villa in Lurin

Lurin villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £685 / night

£4,791 - £11,976 / week

1 / 100

Marigot holiday villa rental

Marigot villa

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 6

from £1,369 / night

£9,581 - £51,895 / week

1 / 100

Vitet holiday villa rental

Vitet villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from £10,265 / night

£71,855 / week

1 / 99

Villa rental in Anse des Cayes

Anse des Cayes villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £1,283 / night

£8,982 - £27,944 / week

1 / 100

Villa rental in Anse des Cayes

Anse des Cayes villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £799 / night

£5,589 - £19,561 / week

1 / 100

Holiday villa rental

Anse de Lorient villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £1,255 / night

£8,783 - £39,920 / week

1 / 100

Holiday villa in Pointe Milou

Pointe Milou villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,255 / night

£8,783 - £41,516 / week

1 / 100

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