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Houses Southold

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135 houses

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

$425

Private Waterfront W Beach, New Renovation

Southold house

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$604

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

$682

Steve's Place Well Furnished 3 BR Southold Home Heated Pool, Town Near Beach

Southold house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$927

3 Bedroom newly renovated private waterfront Beachwood home!

Southold house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$756

Sea Breeze & Sunsets, Private Beach house walk to Vineyards

Southold house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$1,570

3BR Newly renovated Southold Beach Cottage steps to beach close to Greenport

Southold house

3 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$1,049

Great rentals within 20 miles that match your search

North Fork House with Private Beach Access

East Marion house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 24 minutes

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Price per night from

$341

Hampton's Paradise sag Harbor, Southampton

Sag Harbor house

6 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$1,138

Ready for Summer 2021

Southampton house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$1,707

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$1,252

Hampton Bays, south of 27A

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 55 minutes

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Price per night from

$455

Waterfront Southampton Gem! Sailboat On Grounds - Travertine patio and Hot Tub

Water Mill house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$774

East Hampton shingle style home

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$854

North Fork 5 bed room home with forever farm view

Aquebogue house

5 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$455

Cozy North Shore Beach House * Wine Country

Baiting Hollow house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$228

Amagansett Estate 3 BR 60ft Pool

Amagansett house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$1,024

Newly remodeled mid century modern

East Hampton house

4 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$569

Quaint Seaside Retreat With Full Gym

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 33 minutes

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Price per night from

$1,365

SOUTHAMPTON NEW YOK LUXURY RENTAL

Southampton house

4 bedrooms / 11 bathrooms / sleeps 8

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Price per night from

$2,032

Amagansett House with Pool near Village & Beach

Amagansett house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$1,301

East Hampton Dream House 'Serendipity' - Great Buy

East Hampton house

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$569

Hamptons Summer Getaway

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$683

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

$813

East Hampton Village Classic , South of Highway

East Hampton house

7 bedrooms / 9 bathrooms / sleeps 12

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Price per night from

$4,062

Dream house vacation on the Long Island Sound

Orient house

5 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 52 minutes

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Price per night from

$1,081

The Seashell House

Sag Harbor house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$969

Historic Cottage Near Beach!

Greenport house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$380

5 bedroom Private Family Get Away

Westhampton Beach house

5 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$1,368

1200ft2 - Great Hamptons location

Southampton house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$1,140

Live in Luxury in This English Manor Home.

East Hampton house

6 bedrooms / 7 bathrooms / sleeps 12

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Price per night from

$3,704

Summer in a Hamptons Cottage

Bridgehampton house

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$489

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 50 minutes

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Price per night from

$2,508

Relaxing East Hampton Summer Getaway

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$371

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

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 7

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Price per night from

$1,059

Charmimg Beach cottage in Sagaponack

Southampton house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$652

Relax at our East Hampton home

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$896

East Hampton Summer Rental

East Hampton house

5 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$1,140

Viewing 38 of 135
houses in Southold

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