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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 £899 / night

£6,482 - £18,695 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa with swimming pool in Cul de Sac

Cul de Sac villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £415 / night

£2,902 - £7,459 / week

1 / 28

Holiday villa with shared pool in Orient Bay

Orient Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £490 / night

£3,426 / week

1 / 17

Studio rental in Orient Bay

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £88 / night

£617 - £1,234 / week

1 / 21

Holiday apartment with shared pool in Orient Bay

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £117 / night

£774 / week

1 / 22

Holiday hotel apartment rental

Oyster Pond hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £490 / night

£3,426 / week

1 / 8

Holiday villa in Oyster Pond

Oyster Pond villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £505 / night

£3,534 - £5,104 / week

1 / 25

Holiday villa rental

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £634 / night

£4,437 / week

1 / 32

Holiday condo in Philipsburg

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £490 / night

£3,426 / week

1 / 16

Holiday apartment with shared pool in Oyster Pond

Oyster Pond apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £123 / night

£783 / week

1 / 8

Holiday studio rental

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £79 / night

£549 / week

1 / 18

Condo rental in Philipsburg

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £386 / night

£2,697 / week

1 / 13

Holiday hotel apartment with shared pool in Oyster Pond

Oyster Pond hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £420 / night

£2,937 / week

1 / 7

Holiday apartment with shared pool in Oyster Pond

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £405 / night

£2,832 / week

1 / 11

Holiday villa rental

Anse Marcel villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

from £2,804 / night

£19,630 - £32,978 / week

1 / 53

Oyster Pond holiday villa rental

Oyster Pond villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £735 / night

£5,139 - £10,993 / week

1 / 15

Holiday apartment with shared pool in Orient Bay

Orient Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £244 / night

£1,704 - £3,353 / week

1 / 32

Holiday apartment with swimming pool in Orient Bay

Orient Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £177 / night

£1,237 - £2,639 / week

1 / 22

Villa rental in Simpson Bay

Simpson Bay villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

from £2,199 / night

£15,390 - £31,406 / week

1 / 69

Oyster Pond holiday farmhouse rental

Oyster Pond farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £393 / night

£2,748 - £4,716 / week

1 / 24

Holiday villa with swimming pool in Simpson Bay

Simpson Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £393 / night

£2,748 - £5,104 / week

1 / 50

Holiday home rental

Orient Bay house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £275 / night

£1,924 - £4,947 / week

1 / 34

Holiday villa letting

Oyster Pond villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 18

from £1,021 / night

£7,145 - £13,768 / week

1 / 34

Simpson Bay holiday villa rental

Simpson Bay villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £719 / night

£5,025 - £14,133 / week

1 / 45

Villa rental in Oyster Pond with swimming pool

Oyster Pond villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £468 / night

£3,271 - £5,222 / week

1 / 34

Holiday villa with swimming pool in Oyster Pond

Oyster Pond villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £205 / night

£1,429 - £2,061 / week

1 / 22

Holiday home with swimming pool in Oyster Pond

Oyster Pond house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £629 / night

£4,397 - £7,459 / week

1 / 44

Orient Bay holiday home rental

Orient Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £775 / night

£5,418 - £11,385 / week

1 / 37

Holiday apartment with shared pool in Simpson Bay

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £180 / night

£1,257 - £2,748 / week

1 / 41

Villa rental in Oyster Pond with swimming pool

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £373 / night

£2,611 - £5,222 / week

1 / 23

Simpson Bay holiday villa rental

Simpson Bay villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £527 / night

£3,691 - £7,852 / week

1 / 43

Villa rental in Oyster Pond with swimming pool

Oyster Pond villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £505 / night

£3,534 - £6,910 / week

1 / 22

Holiday villa with swimming pool in Oyster Pond

Oyster Pond villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £405 / night

£2,831 - £5,497 / week

1 / 26

Holiday villa with swimming pool in Orient Bay

Orient Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £626 / night

£4,381 - £7,992 / week

1 / 36

Holiday apartment in Simpson Bay

Simpson Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £337 / night

£2,358 - £4,397 / week

1 / 40

Holiday home with swimming pool in Orient Bay

Orient Bay house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £898 / night

£6,282 - £19,630 / week

1 / 32

Villa letting in Oyster Pond with swimming pool

Oyster Pond villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £359 / night

£2,512 - £4,672 / week

1 / 27

Orient Bay holiday home rental

Orient Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £248 / night

£1,732 - £4,480 / week

1 / 40

Oyster Pond holiday villa rental

Oyster Pond villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,044 / night

£7,305 - £15,862 / week

1 / 45

Home rental in Oyster Pond with swimming pool

Oyster Pond house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

from £395 / night

£2,764 - £4,947 / week

1 / 20

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