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Shelter Island Apartments & Vacation Rentals - 40 Rentals Available

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3 Vacation rentals

1 / 17

Shelter Island House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1333

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from $1333 / night

(7)

1 / 20

Shelter Island Heights Cottage

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$341

Very Good (7 reviews)

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from $341 / night

(9)

1 / 31

Shelter Island House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$401

Excellent (9 reviews)

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from $401 / night

Your search has been expanded 34.4 miles to include more rentals

(1)

1 / 24

Greenport House - 4 miles away

  • 3
  • 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$1001

Excellent (1 reviews)

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from $1001 / night

1 / 34

Southold House - 6.5 miles away

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $499 / night

(2)

1 / 5

Southold House - 6.7 miles away

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$322

Excellent (2 reviews)

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from $322 / night

1 / 12

Sag Harbor House - 8.6 miles away

  • 4
  • 6
  • 3 nights min
  • Ask about children
  • Air conditioning

from $800 / night

1 / 28

Sag Harbor House - 9 miles away

  • 5
  • 10
  • 6 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $430 / night

1 / 18

East Hampton House - 10.9 miles away

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $372 / night

(1)

1 / 8

Sag Harbor House - 11.3 miles away

  • 4
  • 10
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

$787

Excellent (1 reviews)

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from $787 / night

(3)

1 / 13

East Hampton House - 11.4 miles away

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$275

Excellent (3 reviews)

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from $275 / night

1 / 13

East Hampton House - 12.2 miles away

  • 4
  • 7
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $725 / night

(4)

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East Hampton House - 12.3 miles away

  • 3
  • 6
  • 14 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$357

Excellent (4 reviews)

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from $357 / night

(3)

1 / 19

Orient House - 12.4 miles away

  • 4
  • 8
  • 14 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$450

Excellent (3 reviews)

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from $450 / night

1 / 14

Cutchogue Cottage - 12.7 miles away

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

from $295 / night

1 / 30

East Hampton House - 13 miles away

  • 6
  • 14
  • 6 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1429

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from $1429 / night

1 / 11

East Hampton House - 14.1 miles away

  • 3
  • 8
  • 9 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1351

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from $1351 / night

1 / 13

Springs House - 15.2 miles away

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$501

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from $501 / night

1 / 14

East Hampton House - 15.6 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $257 / night

1 / 15

East Hampton Cottage - 17.3 miles away

  • 4
  • 7
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $501 / night

(1)

1 / 13

East Hampton House - 17.4 miles away

  • 4
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning

$1001

Excellent (1 reviews)

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from $1001 / night

1 / 12

Water Mill House - 18.1 miles away

  • 5
  • 8
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1429

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from $1429 / night

1 / 11

Southampton House - 20.7 miles away

  • 3
  • 10
  • 1 night min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $501 / night

1 / 19

Southampton Villa - 20.9 miles away

  • -1
  • 9
  • Min stay varies
  • Ask about children
  • Ask about pets

$1251

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from $1251 / night

1 / 11

Amagansett House - 22 miles away

  • 6
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $501 / night

1 / 32

Southampton Cottage - 23.8 miles away

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $120 / night

(1)

1 / 19

Old Saybrook House - 23.8 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning

$257

Excellent (1 reviews)

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from $257 / night

(1)

1 / 18

Old Lyme Cottage - 24.9 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children

$271

Excellent (1 reviews)

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from $271 / night

1 / 34

Hampton Bays House - 25.3 miles away

  • 8
  • 20
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $893 / night

(1)

1 / 27

Amagansett House - 25.3 miles away

  • 4
  • 12
  • Min stay varies
  • Ask about children
  • Air conditioning

$744

Excellent (1 reviews)

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from $744 / night

(1)

1 / 22

Hampton Bays House - 25.6 miles away

  • 5
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1714

Excellent (1 reviews)

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from $1714 / night

(6)

1 / 37

Riverhead House - 27.4 miles away

  • 5
  • 10
  • Min stay varies
  • Child friendly
  • Air conditioning

$350

Excellent (6 reviews)

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from $350 / night

(6)

1 / 35

Montauk House - 30.8 miles away

  • 4
  • 8
  • Min stay varies
  • Ask about children
  • Air conditioning

$300

Very Good (6 reviews)

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from $300 / night

(4)

1 / 55

East Quogue House - 32.1 miles away

  • 2
  • 4
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

$151

Excellent (4 reviews)

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from $151 / night

1 / 8

East Quogue House - 32.4 miles away

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1500

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from $1500 / night

(3)

1 / 9

East Quogue Villa - 32.4 miles away

  • 8
  • 23
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1001

Very Good (3 reviews)

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from $1001 / night

(1)

1 / 23

East Quogue House - 32.5 miles away

  • 3
  • 7
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$401

Excellent (1 reviews)

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from $401 / night

1 / 4

Montauk House - 32.6 miles away

  • 4
  • 8
  • 6 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $964 / night

(5)

1 / 21

New London House - 33.6 miles away

  • 6
  • 13
  • 1 night min
  • Ask about children
  • Air conditioning
  • Pet friendly

$401

Excellent (5 reviews)

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from $401 / night

(1)

1 / 34

Quogue House - 34.4 miles away

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$800

Excellent (1 reviews)

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from $800 / night