Houses Shelter Island

/ Home
/ Vacation Rentals
/ United States
/ New York
/ Long Island
/ Hamptons
/ Shelter Island
Book with confidence.

Updating...

age 0-16
109 Results

Relevance

Price: low to high

Price: high to low

Reviews

Why am I receiving these results?

109 houses

Why am I receiving these results?

Waterfront Charmer on idyllic Shelter Island

Shelter Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types

All filters match

Price per night from

$1,064

Great rentals within 20 miles that match your search

Summer in a Hamptons Cottage

Bridgehampton house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Rental types

All filters match

Price per night from

$492

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$2,519

Beachy Keen - East Hampton NY

East Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$1,374

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

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Rental types

All filters match

Price per night from

$1,064

Charmimg Beach cottage in Sagaponack

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$655

Relax at our East Hampton home

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types

All filters match

Price per night from

$900

Mint Southampton Village 5-BR South of the Highway w Heated Pool

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

Match: Rental types

All filters match

Price per night from

$1,718

Weekly Summer Beach Rental

Old Lyme house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types

All filters match

Price per night from

$328

East Hampton Summer Rental

East Hampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Rental types

All filters match

Price per night from

$1,145

Architect Designed Home in Waterfront Village

Greenport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types

All filters match

Price per night from

$409

Hampton's Paradise sag Harbor, Southampton

Sag Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Rental types

All filters match

Price per night from

$1,145

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types

All filters match

Price per night from

$1,718

PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$430

Hip & Stylish East Hampton Getaway

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Airy & beautiful home!” We had a wonderful stay at this beautiful East Hampton home. The floor plan is open and makes for an easy flow between the airy living space and kitchen and dining area. The bedrooms are large and well appointed with comfortable beds and fresh linens. The setting of the house is on a wooded acre with incredible views out over the trees and the swimming pool below. The huge deck affords an outdoor dining area perfect for summer entertaining. We will definitely be back for another visit to this amazing get away.

Match: Rental types

All filters match

Price per night from

$982

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types

All filters match

Price per night from

$1,661

3 BR Charming CT shore Beach House at Black Point

Niantic house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 14 minutes

Match: Rental types

All filters match

Price per night from

$458

Great Rates in 2019- No Increases In Rates and Over Holiday Weeks

Hampton Bays house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great time in Hamptons” Jackie and al's place is in a great location. Block away from the canal. Minutes away from the beach. Very Nice house. Looking forward to next summer.

Match: Rental types

All filters match

Price per night from

$458

Classic Hamptons Home in beautiful Water Mill - Minimum 2 week rental

Water Mill house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 13

Match: Rental types

All filters match

Price per night from

$1,718

Match: Rental types

All filters match

Price per night from

$779

Spectacular Family Resort in Hampton Bays, NY

Hampton Bays house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 3 hours 16 minutes

Match: Rental types

All filters match

Price per night from

$850

East Hampton shingle style home

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$859

Hamptons Lofty Beach Barn - Pet Friendly

Water Mill house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 38 minutes

Match: Rental types

All filters match

Price per night from

$1,718

Private Waterfront W Beach, New Renovation

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types

All filters match

Price per night from

$831

Amagansett Estate 3 BR 60ft Pool

Amagansett house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$1,145

Newly remodeled mid century modern

East Hampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types

All filters match

Price per night from

$573

Quaint Seaside Retreat With Full Gym

Hampton Bays house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Rental types

All filters match

Price per night from

$1,374

SOUTHAMPTON NEW YOK LUXURY RENTAL

Southampton house

  • 4 bedrooms
  • 11 bathrooms
  • sleeps 8

Match: Rental types

All filters match

Price per night from

$2,045

Amagansett House with Pool near Village & Beach

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Rental types

All filters match

Price per night from

$1,309

SOUTHAMPTON POOL & TENNIS

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Rental types

All filters match

Price per night from

$3,272

Serene & Private East Hampton Summer Rental w/pool

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types

All filters match

Price per night from

$982

East Hampton Village Classic , South of Highway

East Hampton house

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 12

Match: Rental types

All filters match

Price per night from

$12,268

Dream house vacation on the Long Island Sound

Orient house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types

All filters match

Price per night from

$1,088

SEASHELLS BY THE SEA SHORE

Hampton Bays house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

Responds fast! avg. 3 hours 16 minutes

Match: Rental types

All filters match

Price per night from

$1,219

Shorecrest Beach House, 4 bedroom private beach front, new renovation

Southold house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Rental types

All filters match

Price per night from

$915

The Seashell House

Sag Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Rental types

All filters match

Price per night from

$974

Historic Cottage Near Beach!

Greenport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Rental types

All filters match

Price per night from

$382

1200ft2 - Great Hamptons location

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types

All filters match

Price per night from

$1,145

Viewing 38 of 109
houses in Shelter Island

×

Also consider