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Long Island Rentals with Pools

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Long Island Rentals with Pools

181 vacation rentals

Sagaponack Compound

Sagaponack house

7 bedrooms / 4 bathrooms / sleeps 20

Price per night from

$1,660

1 / 78

Waterfront Condo C204 at The Cliffside Resort

Greenport apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 26 minutes

Price per night from

$249

1 / 14

Amagansett House with Pool near Village & Beach

Amagansett house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,139

1 / 11

Hampton Estate Villa Monthly Rental

Water Mill house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$996

1 / 28

Luxury House w Pool 6 acres HAMPTONS!

Wainscott house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 3 minutes

Price per night from

$1,793

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Southampton Waterfront- Beach Home- 2 kayaks!

Southampton house

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 1 hour 38 minutes

Price per night from

$3,586

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Perfect summer haven, ten minutes walk to village

Bellport house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$399

1 / 21

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

Remsenburg house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$73

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4BR Southampton House w/Private Pool & Garden

Southampton house

4 bedrooms / 5 bathrooms / sleeps 7

Responds fast! avg. 55 minutes

Price per night from

$846

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Private Home In Sag Harbor / Southampton With Pool & Jacuzzi

Sag Harbor house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$932

1 / 43

Village Fringe glassy Modern with Pool and Tennis

East Hampton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$256

1 / 19

Ocean Front Cottage Montauk for rent

Montauk cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 43 minutes

Price per night from

$298

1 / 25

Beautiful Hampton Bays Vacation Rental Home

Hampton Bays house

3 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$605

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Newly Renovated in East Hampton

East Hampton house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$747

1 / 11

Your family Hampton home Pool Jacuzzi walk to beach restaurants

Hampton Bays house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$560

1 / 37

Hamptons Summer Rental - East Quogue

East Quogue house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$498

1 / 11

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

$569

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NEW! Cozy Amagansett Home w/Pool - Walk to Beach!

Amagansett house

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 55 minutes

Price per night from

$737

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Waterfront Paradise for boaters & family reunions!

Hampton Bays house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$996

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New! Regal Westhampton House on Moriches Bay!

Westhampton Beach house

5 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 55 minutes

Price per night from

$996

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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 46 minutes

Price per night from

$2,420

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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

$498

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Romantic Shelter Island Cottage w/2 Pools & a Pond

Shelter Island Heights cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 55 minutes

Price per night from

$384

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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

Price per night from

$5,175

1 / 123

Large swimming pool/Walking distance to the bay

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$683

1 / 46

Serene & Private East Hampton Summer Rental w/pool

East Hampton house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$498

1 / 19

The Perfect Getaway! #1

Great Neck house

3 bedrooms / 2 bathrooms / sleeps 2

Responds fast! avg. 3 hours 12 minutes

Price per night from

$125

1 / 13

Quiet and Private in Heart of East Hampton Village

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful Home in Great Location” The Kaufman family takes great pride in their rental homes and it shows - it is close to being in your own home as possible. The Kaufmans are also a delight to deal with, they always deliver as promised. This home was

Price per night from

$1,445

1 / 13

Sag Harbor Perfect For Extended Family and Friends

Sag Harbor house

5 bedrooms / 6 bathrooms / sleeps 10

Responds fast! avg. 2 hours 55 minutes

Price per night from

$1,494

1 / 29

Montauk Oceanfront Estate

Montauk manor house

5 bedrooms / 8 bathrooms / sleeps 10

Responds fast! avg. 2 hours 43 minutes

Price per night from

$7,500

1 / 30

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

Sag Harbor house

5 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 40 minutes

Price per night from

$1,644

1 / 14

Beautiful East Hampton Home w/ Hot Tub & Pool!

East Hampton house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 55 minutes

Price per night from

$563

1 / 29

Luxury Hamptons Quogue Village 4BR Modernist Retre

Quogue house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 17 minutes

Price per night from

$598

1 / 30

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. 2 hours 53 minutes

Price per night from

$356

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Beautiful and sunny hamptons home with pool

East Hampton house

4 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$996

1 / 11

East Hampton Dream House 'Serendipity' - Great Buy

East Hampton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$369

1 / 7

Peaceful, charming, convenient

Bridgehampton house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,196

1 / 13

"Pennies From Heaven"

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 2 hours 57 minutes

Price per night from

$648

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