Westhampton Rentals with Pools

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49 Houses in Westhampton with pools

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Westhampton Waterfront 6 Bedroom Secluded 3 Acre E

Westhampton house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

Responds fast! avg. 2 hours 54 minutes

Match: Swimming pool

All filters match

Price per night from

$1,145

Great rentals within 20 miles that match your search

Romantic Getaway in Southampton (private room/bathroom)

Southampton private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Swimming pool

All filters match

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

Match: Swimming pool

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Price per night from

$1,721

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$1,721

Fantasy Bay Front Country French Villa

Southampton villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Swimming pool

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Price per night from

$2,295

Luxury Oceanfront 8bd House! Pool & Jacuzzi facing Ocean call for Deals!

Westhampton Beach house

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 18

Match: Swimming pool

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Price per night from

$2,004

3BR/2BA- Private Heated Pool Steps to Moriches Bay

Remsenburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$517

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: Swimming pool

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Price per night from

$1,393

Luxury Oceanfront House, Pool+Jacuzzi facing the ocean, call for Deals!

Westhampton Beach house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Swimming pool

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Price per night from

$1,503

Spectacular Family Resort in Hampton Bays, NY

Hampton Bays house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Responds fast! avg. 3 hours 16 minutes

Match: Swimming pool

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Price per night from

$852

Luxury Hamptons Quogue Village 4BR Modernist Retre

Quogue house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$1,721

Quaint Seaside Retreat With Full Gym

Hampton Bays house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$1,377

Beautiful Estate home in the Hamptons, New York

Water Mill villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$6,883

Bishops Pond Southampton NY

Southampton townhouse

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$147

Southampton Water Front Retreat

Southampton cottage

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$3,278

SOUTHAMPTON POOL & TENNIS

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Swimming pool

All filters match

Price per night from

$3,278

5 bedroom Private Family Get Away

Westhampton Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Swimming pool

All filters match

Price per night from

$1,377

Very Private and Tranquil House in wooded estate.

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$1,148

Responds fast! avg. 1 hour 47 minutes

Match: Swimming pool

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Price per night from

$573

Dune Road-Oceanfront Beach House

Westhampton Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Swimming pool

All filters match

Price per night from

$956

Summer Vacation House

Hampton Bays house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$382

Village Fringe Ranch

Water Mill house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$574

Brand new, Hamptons beach house w/gunite pool & spa

East Quogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$2,065

Oceanfront 1-bedroom at Westhampton Beach

Westhampton Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Swimming pool

All filters match

Price per night from

$482

Exquisite Hamptons Mansion Retreat

Water Mill house

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

Match: Swimming pool

All filters match

Price per night from

$631

New Reno Westhampton Beach Heated Pool Steps to Town

Westhampton Beach house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 16

Match: Swimming pool

All filters match

Price per night from

$1,434

Heated Pool 6+ Bedrooms , 4.5 BA

Noyack house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Swimming pool

All filters match

Price per night from

$1,717

The Citadel of Mastic

Mastic house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 15

Match: Swimming pool

All filters match

Price per night from

$859

Boutique Waterfront Home with Pool in Heart of North Fork

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Swimming pool

All filters match

Price per night from

$430

Idyllic North Fork Waterfront Home with Pool

Mattituck house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Swimming pool

All filters match

Price per night from

$430

Wine Country Retreat w/ Dock & Pool on Mattituck Inlet

Mattituck house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Swimming pool

All filters match

Price per night from

$430

Magnificent private Southampton Estate

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Swimming pool

All filters match

Price per night from

$5,151

Hamptons Lofty Beach Barn - Pet Friendly

Water Mill house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 38 minutes

Match: Swimming pool

All filters match

Price per night from

$1,717

Hamptons Lifestyle At Private Refuge On The Ocean With Pool & Near Wine Trail

Westhampton Beach house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Swimming pool

All filters match

Price per night from

$2,289

House for Rent North Fork Long Island

Mattituck house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$1,374

Match: Swimming pool

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Price per night from

$2,518

Match: Swimming pool

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Price per night from

$573

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

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$224

Viewing 38 of 49
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