Southold Rentals

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

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$430

Private Waterfront W Beach, New Renovation

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$831

Sea Breeze Paradise: Beachfront & Panoramic Views

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$388

Goose Creek Getaway: Modern Home with Beach Access

Southold house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Balcony or terrace

All filters match

Price per night from

$300

Great rentals within 20 miles that match your search

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

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

Match: Balcony or terrace

All filters match

Price per night from

$1,718

East Hampton Summer Rental

East Hampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$1,145

Southampton Water Front Retreat

Southampton cottage

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$3,272

SOUTHAMPTON POOL & TENNIS

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Balcony or terrace

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: Balcony or terrace

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: Balcony or terrace

All filters match

Price per night from

$12,268

East End Retreat - Steps to the beach! - Northfork - Monthly Rentals Available!

Baiting Hollow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$801

The Seashell House

Sag Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$974

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

Southampton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$1,023

5 bedroom Private Family Get Away

Westhampton Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$1,374

1200ft2 - Great Hamptons location

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$1,145

East Hampton Classic

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Balcony or terrace

All filters match

Price per night from

$1,145

Brand New Southampton Condo

Southampton condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$492

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$1,718

Fantasy Bay Front Country French Villa

Southampton villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Balcony or terrace

All filters match

Price per night from

$2,290

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$1,661

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.

Responds fast! avg. 3 hours 16 minutes

Match: Balcony or terrace

All filters match

Price per night from

$1,390

Match: Balcony or terrace

All filters match

Price per night from

$779

Waterfront Condo C204 at The Cliffside Resort

Greenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$458

Luxury Hamptons Quogue Village 4BR Modernist Retre

Quogue house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$1,718

Amagansett Estate 3 BR 60ft Pool

Amagansett house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$1,145

Beautiful Estate home in the Hamptons, New York

Water Mill villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$6,870

Amagansett Estate 5 Bedroom 60ft Pool

Amagansett villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$1,603

Bishops Pond Southampton NY

Southampton townhouse

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$147

SOUTHAMPTON NEW YOK LUXURY RENTAL

Southampton house

  • 4 bedrooms
  • 11 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$2,045

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$1,374

Waterfront home: 4 bed, 3 bath, hot tub & more!

East Quogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$401

Magnificent private Southampton Estate

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Balcony or terrace

All filters match

Price per night from

$5,153

piece of Heaven

Mattituck house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Balcony or terrace

All filters match

Price per night from

$1,718

Perfect vacation home minutes to bay and ocean beaches

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$1,432

Match: Balcony or terrace

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Price per night from

$985

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

Springs house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$1,527

Amagansett w/pool last two weeks of August

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Balcony or terrace

All filters match

Price per night from

$1,603

Idyllic Getaway on the CT Shore - Quiet, Peaceful, Stylish

Westbrook house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$306

Viewing 38 of 50
rentals in Southold

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