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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 £915 / night

£6,399 - £19,052 / 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 apartment in Oyster Pond

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £328 / night

£2,290 / week

1 / 19

Holiday condo rental

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £524 / night

£3,664 / week

1 / 30

Holiday apartment in Oyster Pond

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £423 / night

£2,956 / week

1 / 9

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 apartment in Philipsburg

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £169 / night

£1,183 - £1,596 / week

1 / 33

Holiday villa in Anse de Lorient

Anse de Lorient villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £543 / night

£3,795 - £15,964 / week

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Holiday apartment in Philipsburg

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £393 / night

£2,748 / week

1 / 5

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

Oyster Pond holiday condo rental

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £141 / night

£986 / week

1 / 32

Apartment rental in Dawn Beach with shared pool

Dawn Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £345 / night

£2,414 / week

1 / 10

Apartment rental in Oyster Pond

Oyster Pond apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

from £119 / night

£779 - £1,260 / week

1 / 12

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

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Philipsburg holiday villa rental

Philipsburg villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 14

from £2,748 / night

£19,236 / week

1 / 59

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

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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

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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

Vitet holiday villa rental

Vitet villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £886 / night

£6,199 / week

1 / 40

Holiday villa in Toiny

Toiny villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £2,213 / night

£15,487 / week

1 / 34

Anse de Lorient holiday villa rental

Anse de Lorient villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £443 / night

£3,097 / week

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Petit Cul de Sac holiday villa rental

Petit Cul de Sac villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £2,656 / night

£18,589 / week

1 / 40

Anse des Cayes holiday villa rental

Anse des Cayes villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £1,771 / night

£12,391 / week

1 / 33

Holiday villa with swimming pool in Lurin

Lurin villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £2,269 / night

£15,879 / week

1 / 36

Holiday villa letting

Anse des Flamands villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £1,881 / night

£13,168 / week

1 / 40

Holiday villa rental

Petit Cul de Sac villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £7,192 / night

£50,340 / week

1 / 28

Holiday villa in Toiny

Toiny villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £2,213 / night

£15,487 / week

1 / 34

Villa letting in Marigot with swimming pool

Marigot villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £720 / night

£5,036 / week

1 / 30

Holiday villa with swimming pool in Anse des Flamands

Anse des Flamands villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £1,162 / night

£8,132 / week

1 / 33

Holiday villa in Toiny

Toiny villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £1,328 / night

£9,295 / week

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