Shelter Island Rentals

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

Updating...

age 0-16
68 Results

Relevance

Price: low to high

Price: high to low

Reviews

Why am I receiving these results?

68 Houses

Why am I receiving these results?

Waterfront Charmer on idyllic Shelter Island

Shelter Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$1,060

Great rentals within 20 miles that match your search

Hampton Accommodations

Springs private room

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Match: Garden

All filters match

Price per night from

$343

Historic Cottage Near Beach!

Greenport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

All filters match

Price per night from

$380

Very Private and Tranquil House in wooded estate.

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$1,141

East Hampton Classic

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Garden

All filters match

Price per night from

$1,141

Summer in a Hamptons Cottage

Bridgehampton house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

All filters match

Price per night from

$490

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$2,510

Romantic Getaway in Southampton (private room/bathroom)

Southampton private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

All filters match

Price per night from

$354

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

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Garden

All filters match

Price per night from

$1,060

Charmimg Beach cottage in Sagaponack

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$653

Relax at our East Hampton home

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$897

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

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

Match: Garden

All filters match

Price per night from

$1,712

Architect Designed Home in Waterfront Village

Greenport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

All filters match

Price per night from

$408

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$1,712

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

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$428

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: Garden

All filters match

Price per night from

$978

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: Garden

All filters match

Price per night from

$457

Match: Garden

All filters match

Price per night from

$776

Amagansett Estate 3 BR 60ft Pool

Amagansett house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$1,141

Quaint Seaside Retreat With Full Gym

Hampton Bays house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$1,369

Amagansett Estate 5 Bedroom 60ft Pool

Amagansett villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$1,597

SOUTHAMPTON NEW YOK LUXURY RENTAL

Southampton house

  • 4 bedrooms
  • 11 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$2,038

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$1,369

Southampton Water Front Retreat

Southampton cottage

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$3,260

Amagansett House with Pool near Village & Beach

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$1,304

SOUTHAMPTON POOL & TENNIS

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Garden

All filters match

Price per night from

$3,260

East Hampton Village Classic , South of Highway

East Hampton house

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 12

Match: Garden

All filters match

Price per night from

$12,223

Montauk Oceanfront Estate

Montauk manor house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$17,112

Dream house vacation on the Long Island Sound

Orient house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$1,084

Relaxed Village Farmhouse

Greenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$799

"This must be the place"

Greenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$526

Charming cottage in the heart of East Hampton village

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

All filters match

Price per night from

$380

Steps to beach 4bd 2 bth Sleeps 13

Clinton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

Match: Garden

All filters match

Price per night from

$343

Village traditional on a quiet cul de sac

Sag Harbor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$1,271

East Hampton/Sag Harbor Village Fringe

Sag Harbor house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Garden

All filters match

Price per night from

$3,423

Match: Garden

All filters match

Price per night from

$981

Serene and peaceful beach getaway!

Hampton Bays house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$742

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

Springs house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$1,521

Viewing 38 of 68
rentals in Shelter Island

×

Also consider