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Shelter Island Rentals

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282 Results

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282 Houses

Romantic Shelter Island Cottage w/2 Pools & a Pond

Shelter Island Heights cottage

1 bedroom / 2 bathrooms / sleeps 5

Responds fast! avg. 31 minutes

Price per night from

$457

Waterfront Estate on Shelter Island. 200 Ft on Water. 100 Ft Dock.

Shelter Island house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 56 minutes

Price per night from

$839

Luxurious 'Shelter Island Hideaway' w/ Pool!

Shelter Island house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 25 minutes

Price per night from

$585

Waterfront Charmer on idyllic Shelter Island

Shelter Island house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,092

Studio

Shelter Island apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$573

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

$390

Hampton accommodations 2

East Hampton b&b

1 bedroom / 2 bathrooms / sleeps 2

Responds fast! avg. 45 minutes

Price per night from

$293

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

Noyack house

5 bedrooms / 8 bathrooms / sleeps 10

Price per night from

$1,564

Seahaven Resort Motel Unit 12

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$246

Montauk Ocean View Retreat-Rental Registry #16-950

Montauk house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,173

Relaxing East Hampton Summer Getaway

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$382

Seahaven Resort Motel Unit 1

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$234

Tropical Paradise -Year Round Indoor Pool

East Hampton house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$470

Seahaven Resort Motel Unit 10

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$269

Charmimg Beach cottage in Sagaponack

Southampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$671

MONTAUK COTTAGE NEAR THE SEA

Montauk cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$391

Newly Remodeled Home Down the Street from the Beach & Short Drive to Vineyards

Sag Harbor chalet

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 31 minutes

Price per night from

$588

Rare Waterfront Experience :: Forever Bay Vistas ::

New Suffolk house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,134

Seahaven Resort Motel Unit 13

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$246

Cottage european charm private beach in Southampton, North Sea

Southampton house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$554

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

Springs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,567

Charming Southampton cottage

Southampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$470

East Hampton shingle style home

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$882

Bridgehampton Spotless Designer Home Heated Saline Pool, READ OUR REVIEWS

Bridgehampton house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 52 minutes

Price per night from

$588

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

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$1,092

Fully Renovated Beautiful Montauk Waterfront Condo

Montauk condo

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$500

Direct Waterfront Home - Enjoy all summer long

Old Saybrook house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,174

Seahaven Resort Motel Unit 8

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$234

Southampton Village Charmer with New Heated Pool

Southampton house

4 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$1,763

piece of Heaven

Mattituck house

4 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$1,763

Elegant Restored Sea Captain House

East Hampton house

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$756

Price per night from

$671

Seahaven Resort Motel Unit 11

Southampton hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$246

Summer Vacation House

Hampton Bays house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$392

East Hampton Dream House 'Serendipity' - Great Buy

East Hampton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$435

Hamptons Lofty Beach Barn - Pet Friendly

Water Mill house

4 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 2 hours 30 minutes

Price per night from

$999

Ultimate Summer Comfort - Clean, Comfortable, Spac

Montauk house

3 bedrooms / 5 bathrooms / sleeps 6

Price per night from

$671

THE PERFECT HAMPTON'S BEACH HOUSE 200 FT TO OCEAN

Amagansett house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$924

Viewing 38 of 282
rentals in Shelter Island

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