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Hamptons Rentals with Pools

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Hamptons Rentals with Pools

168 vacation rentals

Amagansett Estate 3 BR 60ft Pool

Amagansett house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$1,200

1 / 23

Romantic Shelter Island Cottage w/2 Pools & a Pond

Shelter Island Heights cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 7 minutes

Price per night from

$385

1 / 24

Village Fringe glassy Modern with Pool and Tennis

East Hampton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$243

1 / 19

East Hampton Family Retreat with Cottage

East Hampton house

5 bedrooms / 4 bathrooms / sleeps 12

“Great House, Great Host” My friends and I spent a great weekend at this house and were blown away by house nice the house was and how gracious Leanna was as a host. We made good use of the pool (played several house of pool volleyball) and the hot tu

Responds fast! avg. 3 hours 50 minutes

Price per night from

$600

1 / 41

Hampton Estate Villa Monthly Rental

Water Mill house

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$1,000

1 / 28

4BR Southampton House w/Private Pool & Garden

Southampton house

4 bedrooms / 5 bathrooms / sleeps 7

Responds fast! avg. 21 minutes

Price per night from

$849

1 / 28

5 bedroom Private Family Get Away

Westhampton Beach house

5 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 45 minutes

Price per night from

$300

1 / 45

Hamptons Summer Rental - East Quogue

East Quogue house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$495

1 / 11

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

$2,429

1 / 28

Sagaponack Compound

Sagaponack house

7 bedrooms / 4 bathrooms / sleeps 20

Price per night from

$1,666

1 / 78

Ocean Front Cottage Montauk for rent

Montauk cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 6 minutes

Price per night from

$299

1 / 25

Newly Renovated in East Hampton

East Hampton house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$750

1 / 11

NEW! 7BR Sag Harbor Home w/Pool & Tennis Court!

Sag Harbor house

7 bedrooms / 7 bathrooms / sleeps 14

Responds fast! avg. 21 minutes

Price per night from

$1,500

1 / 32

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

1 / 6

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

$429

1 / 24

New! Regal Westhampton House on Moriches Bay!

Westhampton Beach house

5 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 7 minutes

Price per night from

$1,000

1 / 34

CHIC RETREAT!! Walk to Desirable Bay BEACH!!

East Hampton house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 34 minutes

Price per night from

$2,178

1 / 26

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

Amagansett house

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 21 minutes

Price per night from

$740

1 / 24

East Hampton House w/Private Pool - 5 min to Beach

East Hampton house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 7 minutes

Price per night from

$560

1 / 24

Waterfront Paradise for boaters & family reunions!

Hampton Bays house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$1,000

1 / 14

East Hampton Gem

East Hampton house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 50 minutes

Price per night from

$1,400

1 / 16

Beautiful Hampton Bays Vacation Rental Home

Hampton Bays house

3 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$607

1 / 27

Private Beach Getaway

Springs house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 41 minutes

Price per night from

$400

1 / 28

Southampton 2018 - Garden Jewel is Ready for Your Family

Southampton house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 44 minutes

Price per night from

$975

1 / 37

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

$1,800

1 / 20

ROMANTIC LUXURY RETREAT WITH POOL & WATER VIEWS, 1 MILE FROM SAG HARBOR VILLAGE

Sag Harbor house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$795

1 / 15

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

$500

1 / 15

East Hampton Village Home - Pristine Condition

East Hampton house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,410

1 / 24

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

Remsenburg house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$73

1 / 21

Fabulous Southampton Luxury Mansard with Gunite Heated Pool, Sonos Music & More

Southampton house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,050

1 / 45

Amagansett House with Pool near Village & Beach

Amagansett house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,143

1 / 11

"Pennies From Heaven"

Hampton Bays house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 2 hours 57 minutes

Price per night from

$650

1 / 25

Your family Hampton home Pool Jacuzzi walk to beach restaurants

Hampton Bays house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$570

1 / 37

Spacious Home with Pool in Heart of the Hamptons!

Water Mill house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,000

1 / 33

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

$1,200

1 / 20

Beautiful Estate home in the Hamptons, New York

Water Mill villa

7 bedrooms / 7 bathrooms / sleeps 10

Price per night from

$3,999

1 / 20

Serene East Hampton Apt. w/ Private Yard & Pool!

East Hampton apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 7 minutes

Price per night from

$85

1 / 24

6BR Montauk House w/Pool & Ocean Views!

Montauk house

6 bedrooms / 4 bathrooms / sleeps 13

Responds fast! avg. 7 minutes

Price per night from

$1,800

1 / 25
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