Southold Rentals

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158 Houses

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

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$427

Private Waterfront W Beach, New Renovation

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$829

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

Southold house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$909

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

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$407

Modern North Fork Haven: Beachfront,Private Pool

Southold house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Price per night from

$842

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

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$450

Sea Breeze Paradise: Beachfront & Panoramic Views

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$596

Boutique Waterfront Home with Pool in Heart of North Fork

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$429

Goose Creek Getaway: Modern Home with Beach Access

Southold house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$368

Great rentals within 20 miles that match your search

East Hampton Summer Rental

East Hampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,138

Architect Designed Home in Waterfront Village

Greenport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$406

Beautiful 3 BR 3BA-Pool,Tennis, Home Theater, even a Tesla Charger

East Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$683

Amagansett House with Pool near Village & Beach

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,300

SOUTHAMPTON POOL & TENNIS

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$3,249

Serene & Private East Hampton Summer Rental w/pool

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$975

East Hampton Village Classic , South of Highway

East Hampton house

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 12

Price per night from

$12,184

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

Baiting Hollow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$795

Dream house vacation on the Long Island Sound

Orient house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$1,081

SEASHELLS BY THE SEA SHORE

Hampton Bays house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

Responds fast! avg. 1 hour 17 minutes

Price per night from

$1,210

Elegance,Privacy, French Farm House

East Hampton farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$1,081

Hampton Accommodations

Springs private room

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

Price per night from

$342

The Seashell House

Sag Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$967

Historic Cottage Near Beach!

Greenport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$379

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

Southampton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$1,016

5 bedroom Private Family Get Away

Westhampton Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$1,365

1200ft2 - Great Hamptons location

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$1,138

Very Private and Tranquil House in wooded estate.

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,138

East Hampton Classic

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Price per night from

$1,246

Brand New Southampton Condo

Southampton condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$488

Summer in a Hamptons Cottage

Bridgehampton house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$488

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$2,502

Romantic Getaway in Southampton (private room/bathroom)

Southampton private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$353

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

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$1,057

Charmimg Beach cottage in Sagaponack

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$651

Relax at our East Hampton home

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$894

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

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

Price per night from

$1,706

Hampton's Paradise sag Harbor, Southampton

Sag Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$1,138

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,706

Viewing 38 of 158
rentals in Southold

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