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Family Friendly Holidays in Shelter Island - Holiday Lettings

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103 family friendly properties

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Shelter Island holiday home rental

Shelter Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £837 / night

£5,853 / week

1 / 19

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £472 / night

£3,303 / week

1 / 23

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £468 / night

£3,270 / week

1 / 24

Shelter Island Heights ski cottage to rent.

Shelter Island Heights cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £250 / night

£1,751 / week

1 / 18

Shelter Island Heights holiday home rental

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £361 / night

£2,522 / week

1 / 21

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £1,293 / night

£9,050 / week

1 / 30

Shelter Island Heights holiday home accommodation

Shelter Island Heights house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from £728 / night

£5,092 / week

1 / 30

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £767 / night

£5,368 / week

1 / 24

Home rental in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

from £641 / night

£4,481 / week

1 / 24

Shelter Island Heights holiday home rental

Shelter Island Heights house

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

from £1,571 / night

£10,994 / week

1 / 30

Ski home to rent in Shelter Island Heights

Shelter Island Heights house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £578 / night

£4,046 / week

1 / 30

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £440 / night

£3,078 / week

1 / 26

Shelter Island Heights ski home to rent.

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £890 / night

£6,226 / week

1 / 28

Shelter Island Heights ski home to rent.

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,108 / night

£7,757 / week

1 / 30

Shelter Island Heights ski home to rent.

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £437 / night

£3,056 / week

1 / 30

Shelter Island Heights holiday home rental

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £596 / night

£4,173 / week

1 / 21

Shelter Island Heights holiday home rental

Shelter Island Heights house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,718 / night

£12,023 / week

1 / 30

Shelter Island Heights holiday home let

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £629 / night

£4,399 / week

1 / 22

Ski home to rent in Shelter Island Heights

Shelter Island Heights house

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 14

from £1,862 / night

£13,030 / week

1 / 30

Home rental in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £453 / night

£3,166 / week

1 / 27

Shelter Island Heights holiday home rental

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £628 / night

£4,393 / week

1 / 22

Holiday home rental

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £217 / night

£1,514 / week

1 / 27

Shelter Island Heights holiday home rental

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £703 / night

£4,922 / week

1 / 30

Shelter Island Heights holiday home rental

Shelter Island Heights house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

from £590 / night

£4,129 / week

1 / 24

Shelter Island Heights ski home to rent.

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £669 / night

£4,680 / week

1 / 13

Ski home to rent in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £478 / night

£3,342 / week

1 / 30

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £936 / night

£6,551 / week

1 / 30

Ski home to rent in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from £708 / night

£4,955 / week

1 / 22

Home letting in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

from £810 / night

£5,665 / week

1 / 20

Shelter Island Heights holiday home rental

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £590 / night

£4,129 / week

1 / 23

Shelter Island Heights ski home to rent.

Shelter Island Heights house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £1,298 / night

£9,083 / week

1 / 30

Shelter Island Heights holiday home rental

Shelter Island Heights house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £524 / night

£3,667 / week

1 / 30

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £708 / night

£4,955 / week

1 / 24

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

from £505 / night

£3,535 / week

1 / 30

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £983 / night

£6,881 / week

1 / 21

Shelter Island Heights holiday home rental

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £354 / night

£2,478 / week

1 / 27

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £383 / night

£2,681 / week

1 / 30

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

from £787 / night

£5,505 / week

1 / 27

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

from £1,309 / night

£9,160 / week

1 / 28

Ski home to rent in Shelter Island Heights

Shelter Island Heights house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £590 / night

£4,129 / week

1 / 23

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