Houses in Shelter Island and Villas – Holiday Lettings - Holiday Rentals Shelter Island

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287 Holiday homes

(2) Excellent 

30

Shelter Island holiday home rental

Hamptons / Shelter Island

4 8 15 nights min

  • 4 bedrooms
  • sleeps 8
  • 15 nights min
  • Nearest beach 1 km
  • Child friendly
  • Air conditioning

from £226 / night

£991 / week

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from £226 / night

26

Shelter Island holiday home let

Hamptons / Shelter Island

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £379 / night

£2,650 / week

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Responds fast!
avg. 1 hour 7 minutes

from £379 / night

24

Holiday cottage with swimming pool in Shelter Island Heights

Shelter Island / Shelter Island Heights

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £295 / night

£2,062 / week

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Responds fast!
avg. 1 hour 7 minutes

from £295 / night

35

Holiday bungalow in Shelter Island Heights

Shelter Island / Shelter Island Heights

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £459 / night

£3,207 / week

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Responds fast!
avg. 3 hours 57 minutes

from £459 / night

49

Holiday villa in Shelter Island Heights

Shelter Island / Shelter Island Heights

6 12 15 nights min

  • 6 bedrooms
  • sleeps 12
  • 15 nights min
  • Ask owner if suitable for children
  • Ask about pets

from £3,068 / night

£21,471 / week

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Responds fast!
avg. 2 hours 27 minutes

from £3,068 / night

19

Shelter Island holiday home rental

Hamptons / Shelter Island

3 8 14 nights min

  • 3 bedrooms
  • sleeps 8
  • 14 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £711 / night

£4,972 / week

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from £711 / night