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Shelter Island Rentals

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189 Results

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189 Houses

Luxurious 'Shelter Island Hideaway' w/ Pool!

Shelter Island Heights house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 46 minutes

Price per night from

$615

Waterfront Charmer on idyllic Shelter Island

Shelter Island house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,059

Great rentals within 20 miles that match your search

Historic Cottage Near Beach!

Greenport house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$432

Summer Shangri La on Sag Harbor Memorial Day to Labor Day!!

Noyack house

5 bedrooms / 8 bathrooms / sleeps 10

Price per night from

$1,733

Seahaven Resort Motel Unit 12

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$272

Montauk Ocean View Retreat-Rental Registry #16-950

Montauk house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,300

Seahaven Resort Motel Unit 1

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$259

Seahaven Resort Motel Unit 10

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$298

Seahaven Resort Motel Unit 13

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$273

Vacation home in Artistic / Historic area of East Hampton, NY

Springs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,737

East Hampton shingle style home

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$977

Airy, Woodsy, Walk to Beach, New Saltwater Pool!

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$1,210

Seahaven Resort Motel Unit 8

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$260

piece of Heaven

Mattituck house

4 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$1,954

Seahaven Resort Motel Unit 11

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$273

Summer Vacation House

Hampton Bays house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$434

1200ft2 - Great Hamptons location

Southampton house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,303

SOUTHAMPTON NEW YOK LUXURY RENTAL

Southampton house

4 bedrooms / 11 bathrooms / sleeps 8

Price per night from

$2,327

Seahaven Resort Motel Unit 6

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$260

Seahaven Resort Motel Unit 17

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$260

The Seashell House

Sag Harbor house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,108

Beach House on Private Treasure Island Drive

Amagansett house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,916

Seahaven Resort Motel Unit 3

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$273

Seahaven Resort Motel Unit 7

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$234

East Hampton Summer Rental

East Hampton house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,303

Relax at our East Hampton home

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$1,024

Perfect vacation home minutes to bay and ocean beaches

East Hampton house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,628

Seahaven Resort Motel Unit 4

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$273

Seahaven Resort Motel Unit 16

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 1

Price per night from

$273

Seahaven Resort Motel Unit 5

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$273

Seahaven Resort Motel Unit 14

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$273

Waterfront Southampton Gem! Sailboat On Grounds - Travertine patio and Hot Tub

Water Mill house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$886

Brand New Southampton Condo

Southampton condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$559

Seahaven Resort Motel Unit 2

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$273

Seahaven Resort Motel Unit 15

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$390

Seahaven Resort Motel Unit 9

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$273

ONE-OF-A-KIND VILLA NESTLED ALONG THE SHORE

Southampton villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$1,163

Sophisticated Village Home - Serene Setting - Lovely Pool and Garden

Southampton house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$1,116

Viewing 38 of 189
rentals in Shelter Island

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