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Villas in Windward: Rent luxury villas in Windward

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Windward holiday villa rental

Pointe Milou villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £913 / night

£6,388 - £19,019 / week

1 / 24

Great rentals within 20 miles that match your search

Cul de Sac holiday villa rental

Cul de Sac villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £799 / night

£5,590 - £11,179 / week

1 / 56

Villa rental in Cul de Sac

Cul de Sac villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £403 / night

£2,817 - £5,232 / week

1 / 28

Oyster Pond holiday villa rental

Oyster Pond villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £1,828 / night

£15,360 / week

1 / 28

Holiday villa in Little Bay

Little Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £457 / night

£3,194 - £9,582 / week

1 / 42

Holiday villa in Pelican Key

Pelican Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £458 / night

£3,200 / week

1 / 16

Philipsburg holiday villa rental

Philipsburg villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £202 / night

£1,408 / week

1 / 21

Villa rental in Orient Bay

Orient Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £500 / night

£3,497 / week

1 / 53

Villa letting in Orient Bay

Orient Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £441 / night

£3,086 / week

1 / 37

Holiday villa with swimming pool in Orient Bay

Orient Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £250 / night

£1,749 / week

1 / 39

Villa rental in Oyster Pond with swimming pool

Oyster Pond villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

from £490 / night

£3,426 - £7,188 / week

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Oyster Pond holiday villa rental

Oyster Pond villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £690 / night

£4,830 / week

1 / 26

Holiday villa in Simpson Bay

Simpson Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £156 / night

£1,088 / week

1 / 19

Holiday villa with swimming pool in Pelican Key

Pelican Key villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £685 / night

£4,791 - £7,985 / week

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Holiday villa with swimming pool in Orient Bay

Orient Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

from £196 / night

£1,372 / week

1 / 14

Orient Bay holiday villa rental

Orient Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £599 / night

£4,192 - £8,384 / week

1 / 35

Villa rental in Orient Bay with swimming pool

Orient Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £345 / night

£2,415 - £4,360 / week

1 / 25

Holiday villa with shared pool in Pelican Key

Pelican Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £108 / night

£686 / week

1 / 0

Holiday villa in Upper Prince's Quarter

Upper Prince's Quarter villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £503 / night

£3,514 - £5,590 / week

1 / 49

Holiday villa in Gustavia

Gustavia villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,568 / night

£10,970 - £47,994 / week

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Orient Bay holiday villa rental

Orient Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £637 / night

£4,453 - £11,962 / week

1 / 55

Holiday villa in Philipsburg

Philipsburg villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £170 / night

£1,184 - £1,280 / week

1 / 17

Villa accommodation in Philipsburg

Philipsburg villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,554 / night

£10,874 / week

1 / 12

Oyster Pond holiday villa rental

Oyster Pond villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £571 / night

£3,997 - £7,188 / week

1 / 51

Villa rental in Anse Marcel

Anse Marcel villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £547 / night

£3,829 - £8,619 / week

1 / 31

Holiday villa in Cole Bay

Cole Bay villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from £636 / night

£4,448 / week

1 / 26

Oyster Pond holiday villa rental

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £380 / night

£2,655 - £5,031 / week

1 / 48

Little Bay holiday villa accommodation

Little Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,677 / night

£11,738 - £27,947 / week

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Holiday villa in Little Bay

Little Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,677 / night

£11,738 - £27,947 / week

1 / 70

Holiday villa with swimming pool in Little Bay

Little Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,355 / night

£9,481 - £22,625 / week

1 / 57

Holiday villa in Orient Bay

Orient Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £538 / night

£3,765 - £8,086 / week

1 / 43

Holiday villa in Anse de Lorient

Anse de Lorient villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

from £867 / night

£19,326 / week

1 / 18

Holiday villa with swimming pool in Orient Bay

Orient Bay villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £2,955 / night

£14,775 - £20,638 / week

1 / 14

Holiday villa with swimming pool in Orient Bay

Orient Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £400 / night

£2,795 / week

1 / 24

Holiday villa with swimming pool in Vitet

Vitet villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £399 / night

£2,790 - £9,564 / week

1 / 21

Holiday villa with swimming pool in Gustavia

Gustavia villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £365 / night

£2,551 - £26,700 / week

1 / 22

Pelican Key holiday villa rental

Pelican Key villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

from £2,232 / night

£15,621 - £26,779 / week

1 / 44

Holiday villa in Oyster Pond

Oyster Pond villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £319 / night

£2,232 - £4,185 / week

1 / 49

Holiday villa in Cul de Sac

Cul de Sac villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £344 / night

£2,407 / week

1 / 20

Holiday villa in Gustavia

Gustavia villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £2,163 / night

£17,156 / week

1 / 38

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