Shelter Island Rentals

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150 Houses

Waterfront Charmer on idyllic Shelter Island

Shelter Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,063

Great rentals within 20 miles that match your search

1200ft2 - Great Hamptons location

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$1,144

Very Private and Tranquil House in wooded estate.

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,144

East Hampton Classic

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Price per night from

$1,144

Brand New Southampton Condo

Southampton condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$491

Summer in a Hamptons Cottage

Bridgehampton house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$491

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$2,516

Romantic Getaway in Southampton (private room/bathroom)

Southampton private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$355

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

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$1,063

Charmimg Beach cottage in Sagaponack

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$655

Relax at our East Hampton home

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$899

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

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

Price per night from

$1,716

East Hampton Summer Rental

East Hampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,144

Architect Designed Home in Waterfront Village

Greenport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$409

Hampton's Paradise sag Harbor, Southampton

Sag Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,144

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,716

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

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$429

Fantasy Bay Front Country French Villa

Southampton villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$2,287

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.

Price per night from

$899

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$1,659

Majestic Southampton Waterfront Estate

Southampton villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

“Incredible home” This was the perfect home for my husband, kids and grandkids. I can't begin to describe how incredible this home was. From the amazing outdoor kitchen, magnificent landscaping, the toasty warm huge pool, with seating enough for our supersized family of 20 with 4 grandbabies. This home was able to house us all comfortably. The inside of the house was clean, spacious and beautifully decorated. The high count sheets were a dream to sleep on (cute pun intended). The air conditioning was set to the perfect temperature. Every day all of us lived in the pool and at night enjoyed the gorgeous sunsets over the bay. To say we loved this home is an understatement. We are still all talking about the amazing vacation. The owner was really really nice to deal with and made us feel welcomed.

Price per night from

$1,389

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.

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

Price per night from

$1,716

Price per night from

$778

Spectacular Family Resort in Hampton Bays, NY

Hampton Bays house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Price per night from

$849

Waterfront Condo C204 at The Cliffside Resort

Greenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$458

East Hampton shingle style home

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$858

Amagansett Estate 3 BR 60ft Pool

Amagansett house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$1,144

Newly remodeled mid century modern

East Hampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$572

Quaint Seaside Retreat With Full Gym

Hampton Bays house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,373

Beautiful Estate home in the Hamptons, New York

Water Mill villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 10

Price per night from

$6,862

Amagansett Estate 5 Bedroom 60ft Pool

Amagansett villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$1,601

Bishops Pond Southampton NY

Southampton townhouse

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 8

Price per night from

$147

SOUTHAMPTON NEW YOK LUXURY RENTAL

Southampton house

  • 4 bedrooms
  • 11 bathrooms
  • sleeps 8

Price per night from

$2,043

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,373

Southampton Water Front Retreat

Southampton cottage

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 10

Price per night from

$3,268

Amagansett House with Pool near Village & Beach

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,307

SOUTHAMPTON POOL & TENNIS

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$3,268

Viewing 38 of 150
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