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Hamptons Rentals with Pools

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Hamptons Rentals with Pools

178 vacation rentals

Sagaponack Compound

Sagaponack house

7 bedrooms / 4 bathrooms / sleeps 20

Price per night from

$1,432

1 / 78

4BR Southampton House w/Private Pool & Garden

Southampton house

4 bedrooms / 5 bathrooms / sleeps 7

Responds fast! avg. 38 minutes

Price per night from

$971

1 / 28

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

Remsenburg house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$84

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Luxury House w Pool 6 acres HAMPTONS!

Wainscott house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 48 minutes

Price per night from

$2,061

1 / 20

Amagansett House with Pool near Village & Beach

Amagansett house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,309

1 / 11

Romantic Shelter Island Cottage w/2 Pools & a Pond

Shelter Island Heights cottage

1 bedroom / 2 bathrooms / sleeps 6

Responds fast! avg. 41 minutes

Price per night from

$441

1 / 24

Newly Renovated in East Hampton

East Hampton house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$858

1 / 11

Hampton Estate Villa Monthly Rental

Water Mill house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$953

1 / 28

Ocean Front Cottage Montauk for rent

Montauk cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 51 minutes

Price per night from

$299

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Peaceful, charming, convenient

Bridgehampton house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,374

1 / 13

Southampton Waterfront- Beach Home- 2 kayaks!

Southampton house

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 1 hour 45 minutes

Price per night from

$1,947

1 / 28

Beech Tree Cottage

Sag Harbor cottage

2 bedrooms / 1 bathroom / sleeps 4

“Loved this place” This is the perfect little getaway for those who wish to avoid the pretentiousness of East Hampton and Southampton and still enjoy everything that the Hamptons has to offer. Best things - very cute little cottage. Good enough spa

Price per night from

$572

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Private Home In Sag Harbor / Southampton With Pool & Jacuzzi

Sag Harbor house

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 29 minutes

Price per night from

$932

1 / 44

8 BR Luxury Oceanfront house pool+Jacuzzi On Ocean,Call For Last Minute Deals!

Westhampton Beach house

8 bedrooms / 7 bathrooms / sleeps 18

Price per night from

$1,748

1 / 45

Sag Harbor Home w/ Pool - 5 Mins to Downtown!

Sag Harbor house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 32 minutes

Price per night from

$602

1 / 28

Village Fringe glassy Modern with Pool and Tennis

East Hampton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$294

1 / 19

Hamptons Summer Rental - East Quogue

East Quogue house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$573

1 / 11

Spacious Amagansett Home w/ Pool - Walk to Beach!

Amagansett house

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 19 minutes

Price per night from

$846

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Elegant Designer Hamptons Retreat in Sag Harbor

Sag Harbor house

5 bedrooms / 7 bathrooms / sleeps 12

“Excellent vacation!” Beautifully decorated Designer home was fully furnished with great touches you would expect in a high end rental--soft linens and towels, mini ipods in docking stations around the house, fully stocked kitchen, fabulous pool and ba

Responds fast! avg. 2 hours 39 minutes

Price per night from

$2,777

1 / 28

Luxury Hamptons Quogue Village 4BR Modernist Retre

Quogue house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$687

1 / 30

July - August 2017. Open floor plan, modernist house in the Village of Springs

East Hampton house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$287

1 / 6

Large swimming pool/Walking distance to the bay

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 21 minutes

Price per night from

$785

1 / 46

Serene & Private East Hampton Summer Rental w/pool

East Hampton house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$572

1 / 19

"Pennies From Heaven"

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 2 hours 13 minutes

Price per night from

$745

1 / 25

Montauk Oceanfront Estate

Montauk manor house

5 bedrooms / 8 bathrooms / sleeps 10

Responds fast! avg. 2 hours 51 minutes

Price per night from

$9,985

1 / 30

Beautiful Hampton Bays Vacation Rental Home

Hampton Bays house

3 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$695

1 / 27

East Hampton Dream House 'Serendipity' - Great Buy

East Hampton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$423

1 / 7

Beautiful East Hampton Home w/ Hot Tub & Pool!

East Hampton house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 41 minutes

Price per night from

$647

1 / 29

Perfect Hamptons Rental with Pool and Tennis

Bridgehampton house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 21 minutes

Price per night from

$653

1 / 13

Beautiful and sunny hamptons home with pool

East Hampton house

4 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,145

1 / 11

Amagansett Estate 3 BR 60ft Pool

Amagansett house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,029

1 / 23

Sag Harbor designer home, Chef's kitchen & one block from the water

Sag Harbor house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$1,890

1 / 14

The Graybarn Cottage in the Heart of East Hampton

East Hampton house

4 bedrooms / 4 bathrooms / sleeps 12

“Amazing birthday celebration!” 5 out of 5. Our weekend at Graybarn was the celebration of a lifetime. It was my husband's 50th birthday, and we were celebrating his remission from lymphoma. We invited three other couples as our guest and had the most

Responds fast! avg. 3 hours 47 minutes

Price per night from

$5,175

1 / 123

Chic and Modern Beach retreat with heated Pool

Sag Harbor house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 29 minutes

Price per night from

$795

1 / 16

chic, comfortable home with pool

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$590

1 / 15

Luxurious ‘Shelter Island Hideaway’ w/ Pool!

Shelter Island house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 41 minutes

Price per night from

$567

1 / 26

Southampton Beach Home -Great Location

Water Mill house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 11 minutes

Price per night from

$1,372

1 / 20

Hip & Stylish East Hampton Getaway

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful stay” Me, my husband and our daughter rented this nice house for a week. It was really great, Patricia was so nice and helpful from the start when we wanted to rent it until we left. The house is light, nicely furnished, comfortable beds wi

Responds fast! avg. 3 hours 10 minutes

Price per night from

$572

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