Greenport Rentals

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38 Houses

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Greenport Beach House

Greenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

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Price per night from

$916

Great rentals within 20 miles that match your search

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$2,524

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

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Private outdoor pool (heated)

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Price per night from

$1,066

Ready for Summer 2021

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,721

Fantasy Bay Front Country French Villa

Southampton villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

All filters match

Price per night from

$2,295

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.

Match: Private outdoor pool (heated)

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Price per night from

$984

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

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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. 3 hours 16 minutes

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,393

Amagansett Estate 3 BR 60ft Pool

Amagansett house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$1,148

Beautiful Estate home in the Hamptons, New York

Water Mill villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$6,883

Amagansett Estate 5 Bedroom 60ft Pool

Amagansett villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,606

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,377

Southampton Water Front Retreat

Southampton cottage

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$3,278

Amagansett House with Pool near Village & Beach

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,312

SOUTHAMPTON POOL & TENNIS

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

All filters match

Price per night from

$3,278

East Hampton Village Classic , South of Highway

East Hampton house

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

All filters match

Price per night from

$12,291

Elegance,Privacy, French Farm House

East Hampton farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,090

Village traditional on a quiet cul de sac

Sag Harbor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,278

Match: Private outdoor pool (heated)

All filters match

Price per night from

$987

Amagansett w/pool last two weeks of August

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,606

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

East Hampton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,922

Family Vacation Home, heated pool

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,090

Exquisite Hamptons Mansion Retreat

Water Mill house

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

Match: Private outdoor pool (heated)

All filters match

Price per night from

$631

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

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$343

Chic 3 Bed Cottage w/Modern Pool, 5 Mins from Town

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$658

Heated Pool 6+ Bedrooms , 4.5 BA

Noyack house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,717

Boutique Waterfront Home with Pool in Heart of North Fork

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

All filters match

Price per night from

$430

Magnificent private Southampton Estate

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated)

All filters match

Price per night from

$5,151

Beachy Keen - East Hampton NY

East Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,374

Match: Private outdoor pool (heated)

All filters match

Price per night from

$2,518

Beautiful Bridgehampton Home

Bridgehampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,717

East Hampton Classic

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Private outdoor pool (heated)

All filters match

Price per night from

$1,145

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

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$224

Modern North Fork Haven: Beachfront,Private Pool

Southold house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Private outdoor pool (heated)

All filters match

Price per night from

$842

Sweet Retreat: Private Pool, Outdoor Jacuzzi, Coopers Beach

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$470

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

Laurel house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Private outdoor pool (heated)

All filters match

Price per night from

$823

Southampton Retreat: Heated Pool, Hot Tub, Near Beach

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

All filters match

Price per night from

$425

Coastal Haven: Private Pool, Bay Access, Water Sports

Aquebogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

All filters match

Price per night from

$400

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