Southold Rentals

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83 Houses

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

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$431

Private Waterfront W Beach, New Renovation

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$832

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

Southold house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$917

Steve's Place: Heated Pool, 3BR Southold Home, Beach

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 17 minutes

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Price per night from

$224

Modern North Fork Haven: Beachfront,Private Pool

Southold house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 17 minutes

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Price per night from

$842

Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 17 minutes

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Price per night from

$340

Sea Breeze Paradise: Beachfront & Panoramic Views

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 17 minutes

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Price per night from

$388

Goose Creek Getaway: Modern Home with Beach Access

Southold house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 17 minutes

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Price per night from

$300

Great rentals within 20 miles that match your search

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

Southampton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$1,025

5 bedroom Private Family Get Away

Westhampton Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,377

1200ft2 - Great Hamptons location

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$1,148

Very Private and Tranquil House in wooded estate.

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,148

Brand New Southampton Condo

Southampton condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$493

Lushly Landscaped Contemporary With Pool East Hampton North

East Hampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$574

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$2,524

Romantic Getaway in Southampton (private room/bathroom)

Southampton private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$356

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

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

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Price per night from

$1,721

East Hampton Summer Rental

East Hampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$1,148

Amagansett Estate 5 Bedroom 60ft Pool

Amagansett villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$1,607

Bishops Pond Southampton NY

Southampton townhouse

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 8

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Price per night from

$147

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,377

SOUTHAMPTON POOL & TENNIS

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$3,278

Serene & Private East Hampton Summer Rental w/pool

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$984

East Hampton Village Classic , South of Highway

East Hampton house

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 12

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Price per night from

$12,292

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

Baiting Hollow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$802

SEASHELLS BY THE SEA SHORE

Hampton Bays house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$1,221

Elegance,Privacy, French Farm House

East Hampton farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$1,090

The Seashell House

Sag Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$976

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,723

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.

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Price per night from

$984

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$1,664

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. 1 hour 30 minutes

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Price per night from

$1,394

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.

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Price per night from

$460

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

Water Mill house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 13

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Price per night from

$1,723

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Price per night from

$781

Spectacular Family Resort in Hampton Bays, NY

Hampton Bays house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$852

Waterfront Condo C204 at The Cliffside Resort

Greenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$459

Luxury Hamptons Quogue Village 4BR Modernist Retre

Quogue house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,721

Viewing 38 of 83
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