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Southampton Retreat: Heated Pool, Hot Tub, Near Beach

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Heated pool Private outdoor pool (unheated)

All filters match

Price per night from

$424

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

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Rental types Heated pool Private outdoor pool (unheated)

All filters match

Price per night from

$224

North Fork Oasis: Heated Pool, Hot tub, Steps to the beach!

Laurel house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Rental types Heated pool Private outdoor pool (unheated)

All filters match

Price per night from

$821

Sweet Retreat: Private Pool, Outdoor Jacuzzi, Coopers Beach

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Heated pool Private outdoor pool (unheated)

All filters match

Price per night from

$470

Coastal Haven: Private Pool, Bay Access, Water Sports

Aquebogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Heated pool Private outdoor pool (unheated)

All filters match

Price per night from

$399

Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Heated pool Private outdoor pool (unheated)

All filters match

Price per night from

$343

Modern North Fork Haven: Beachfront,Private Pool

Southold house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Rental types Heated pool Private outdoor pool (unheated)

All filters match

Price per night from

$842

Silver Beach Bliss: Luxury Waterfront Home w/ Pool

Baiting Hollow house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Rental types Heated pool Private outdoor pool (unheated)

All filters match

Price per night from

$736

Redding Relaxation Haven - Tranquil Home with Pool, Gardens Galore

Redding house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Rental types Heated pool Private outdoor pool (unheated)

All filters match

Price per night from

$709

The Lindsay Luxurious Estate: Heated Pool, Hot tub, Huge Yard

Wading River house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Rental types Heated pool Private outdoor pool (unheated)

All filters match

Price per night from

$502

These homes match some but not all of your filters. Clear all filters

Spacious Antique Farm House

Madison house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$458

House for Rent North Fork Long Island

Mattituck house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$1,374

Dune Road-Oceanfront Beach House

Westhampton Beach house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$954

Greenport Beach House

Greenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$916

Mountain Retreat - Chimney Hill - 7 Miles to Mount Snow - direct VAST access

Wilmington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$224

East Hampton Charming Cottage South Of the Highway Near Ocean/ Further Lane

East Hampton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$1,918

Village traditional on a quiet cul de sac

Sag Harbor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$1,276

Beautiful Bridgehampton Home

Bridgehampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$1,718

Summer Vacation House

Hampton Bays house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$382

Village Fringe Ranch

Water Mill house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$573

Heated Pool 6+ Bedrooms , 4.5 BA

Noyack house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$1,718

Huge Renovated Home with Heated Pool and Jacuzzi

Queensbury house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 13

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$859

Westport Villa- Luxury Pool & Spa

Westport house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$945

Boutique Waterfront Home with Pool in Heart of North Fork

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$430

Exquisite Hamptons Mansion Retreat

Water Mill house

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$630

New Reno Westhampton Beach Heated Pool Steps to Town

Westhampton Beach house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 16

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$1,432

Relax at our East Hampton home

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Heated pool, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$900

Charming cottage in the heart of East Hampton village

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Heated pool, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$382

Full Basement unit with gorgeous view.

Salem house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 3 match: Heated pool, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$172

Idyllic North Fork Waterfront Home with Pool

Mattituck house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

2 of 3 match: Heated pool, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$430

Wine Country Retreat w/ Dock & Pool on Mattituck Inlet

Mattituck house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

2 of 3 match: Heated pool, Rental types, Private outdoor pool (unheated)

2 of 3 filters match

Price per night from

$430

Amagansett House with Pool near Village & Beach

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$1,309

Luxury home on Lake Champlain, with pool, hot tub, mooring, kayaks, and more

Charlotte house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$1,718

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

East Quogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$2,061

Family Vacation Home, heated pool

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$1,088

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

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$1,064

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

Remsenburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$516

Amagansett w/pool last two weeks of August

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

2 of 3 match: Private outdoor pool (unheated), Rental types, Heated pool

2 of 3 filters match

Price per night from

$1,603

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