Montauk Rentals with Pools

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32 house rentals in Montauk with pools

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Hilltop Haven in Montauk with Heated Pool perfect for Families

Montauk house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Swimming pool

All filters match

Price per night from

$687

Montauk Summer rental

Montauk condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$459

Montauk Royal Atlantic Beach Resort

Montauk condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$573

Montauk Oceanfront Estate

Montauk manor house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

Match: Swimming pool

All filters match

Price per night from

$17,208

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: Swimming pool

All filters match

Price per night from

$2,524

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

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Swimming pool

All filters match

Price per night from

$1,066

Relax at our East Hampton home

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$902

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: Swimming pool

All filters match

Price per night from

$984

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$1,664

Amagansett Estate 3 BR 60ft Pool

Amagansett house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$1,148

Amagansett Estate 5 Bedroom 60ft Pool

Amagansett villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Swimming pool

All filters match

Price per night from

$1,606

Amagansett Estate 4BR 60ft Pool

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$1,377

Amagansett House with Pool near Village & Beach

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$1,312

Serene & Private East Hampton Summer Rental w/pool

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$984

East Hampton Village Classic , South of Highway

East Hampton house

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 12

Match: Swimming pool

All filters match

Price per night from

$12,291

Elegance,Privacy, French Farm House

East Hampton farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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: Swimming pool

All filters match

Price per night from

$1,278

East Hampton/Sag Harbor Village Fringe

Sag Harbor house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Swimming pool

All filters match

Price per night from

$3,442

Match: Swimming pool

All filters match

Price per night from

$987

Vacation home in Artistic / Historic area of East Hampton, NY

Springs house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$1,530

Amagansett w/pool last two weeks of August

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Swimming pool

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: Swimming pool

All filters match

Price per night from

$1,922

Charming cottage in the heart of East Hampton village

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

All filters match

Price per night from

$382

Family Vacation Home, heated pool

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$1,090

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

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$658

East Hampton Classic

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Match: Swimming pool

All filters match

Price per night from

$1,145

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

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$343

Beech Tree Cottage

Sag Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“The cottage experience was relaxing and peaceful with a short wa” Enchanting cottage, very comfortable, enjoyed a little interaction with the owner's family and dog. Very sweet.

Match: Swimming pool

All filters match

Price per night from

$687

Lushly Landscaped Contemporary With Pool East Hampton North

East Hampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$573

Beautiful Bridgehampton Home

Bridgehampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$1,718

Sag Harbor Village Fringe, Great Location

Sag Harbor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Swimming pool

All filters match

Price per night from

$2,290

Beachy Keen - East Hampton NY

East Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

All filters match

Price per night from

$1,374

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