Vacation Rentals with Pool in Hamptons

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Filtering by: Swimming pool

173 vacation rentals
28

4BR Southampton House w/Private Pool & Garden

Hamptons / Southampton

Southampton house

4 7 7 nights min

  • 4 bedrooms
  • sleeps 7
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

Price per night from

$973

Responds fast!
avg. 14 minutes

Price per night from

$973

20

Luxury House w Pool 6 acres HAMPTONS!

Hamptons / Wainscott

Wainscott house

4 8 21 nights min

  • 4 bedrooms
  • sleeps 8
  • 21 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$1,802

Responds fast!
avg. 3 hours 3 minutes

Price per night from

$1,802

(3) Very Good 

21

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

Hamptons / Remsenburg

Remsenburg house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$84

Price per night from

$84

11

Hamptons Summer Rental - East Quogue

Hamptons / East Quogue

East Quogue house

4 10 6 nights min

  • 4 bedrooms
  • sleeps 10
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$573

Price per night from

$573

78

Sagaponack Compound

Hamptons / Sagaponack

Sagaponack house

7 20 min stay varies

  • 7 bedrooms
  • sleeps 20
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$1,374

Price per night from

$1,374

28

Hampton Estate Villa Monthly Rental

Hamptons / Water Mill

Water Mill house

6 12 5 nights min

  • 6 bedrooms
  • sleeps 12
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,000

Price per night from

$1,000

(1) Excellent 

19

Village Fringe glassy Modern with Pool and Tennis

Hamptons / East Hampton

East Hampton house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$257

Price per night from

$257

11

Amagansett House with Pool near Village & Beach

Hamptons / Amagansett

Amagansett house

4 8 21 nights min

  • 4 bedrooms
  • sleeps 8
  • 21 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

Price per night from

$1,309

Price per night from

$1,309

27

Beautiful Hampton Bays Vacation Rental Home

Southampton / Hampton Bays

Hampton Bays house

3 12 3 nights min

  • 3 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$695

Price per night from

$695

43

Private Home In Sag Harbor / Southampton With Pool & Jacuzzi

Hamptons / Sag Harbor

Sag Harbor house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,035

Price per night from

$1,035

11

Newly Renovated in East Hampton

Hamptons / East Hampton

East Hampton house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Private garden

Price per night from

$859

Price per night from

$859

(1) Excellent 

28

Southampton Waterfront- Beach Home- 2 kayaks!

Hamptons / Southampton

Southampton house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$4,122

Responds fast!
avg. 1 hour 38 minutes

Price per night from

$4,122

(5) Excellent 

15

Beech Tree Cottage

Hamptons / Sag Harbor

Sag Harbor cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“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
…see more

Price per night from

$500

Price per night from

$500

13

Peaceful, charming, convenient

Hamptons / Bridgehampton

Bridgehampton house

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,374

Price per night from

$1,374

28

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

Hamptons / Sag Harbor

Sag Harbor house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$525

Price per night from

$525

24

Romantic Shelter Island Cottage w/2 Pools & a Pond

Shelter Island / Shelter Island Heights

Shelter Island Heights cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$441

Responds fast!
avg. 14 minutes

Price per night from

$441

(7) Excellent 

25

Ocean Front Cottage Montauk for rent

Hamptons / Montauk

Montauk cottage

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$299

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$299

24

Spacious Amagansett Home w/ Pool - Walk to Beach!

Hamptons / Amagansett

Amagansett house

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$848

Responds fast!
avg. 14 minutes

Price per night from

$848

14

Waterfront Paradise for boaters & family reunions!

Southampton / Hampton Bays

Hampton Bays house

6 12 14 nights min

  • 6 bedrooms
  • sleeps 12
  • 14 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$1,000

Price per night from

$1,000

(4) Excellent 

123

The Graybarn Cottage in the Heart of East Hampton

Hamptons / East Hampton

East Hampton house

4 12 3 nights min

  • 4 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
“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
…see more

Price per night from

$5,175

Price per night from

$5,175

29

Beautiful East Hampton Home w/ Hot Tub & Pool!

Hamptons / East Hampton

East Hampton house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$647

Responds fast!
avg. 14 minutes

Price per night from

$647

30

Montauk Oceanfront Estate

Hamptons / Montauk

Montauk manor house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$9,995

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$9,995

(1) Excellent 

19

Serene & Private East Hampton Summer Rental w/pool

Hamptons / East Hampton

East Hampton house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$500

Price per night from

$500

(3) Very Good 

30

Luxury Hamptons Quogue Village 4BR Modernist Retre

Hamptons / Quogue

Quogue house

4 8 14 nights min

  • 4 bedrooms
  • sleeps 8
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

Price per night from

$687

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$687

(1) Excellent 

6

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

Hamptons / East Hampton

East Hampton house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Air conditioning

Price per night from

$250

Price per night from

$250

(3)  

15

Westhampton Beach Village LONG ISLAND New York

Hamptons / Westhampton Beach

Westhampton Beach house

5 13 3 nights min

  • 5 bedrooms
  • sleeps 13
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$150

Price per night from

$150

23

Amagansett Estate 3 BR 60ft Pool

Hamptons / Amagansett

Amagansett house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child Friendly

Price per night from

$900

Price per night from

$900

34

Waterfront Westhampton House w/Private Pool & Dock

Hamptons / Westhampton Beach

Westhampton Beach house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,145

Responds fast!
avg. 14 minutes

Price per night from

$1,145

(1) Excellent 

26

East Hampton/Sag Harbor Village Fringe

Hamptons / Sag Harbor

Sag Harbor house

6 12 6 nights min

  • 6 bedrooms
  • sleeps 12
  • 6 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$2,999

Responds fast!
avg. 3 hours 39 minutes

Price per night from

$2,999

13

Perfect Hamptons Rental with Pool and Tennis

Hamptons / Bridgehampton

Bridgehampton house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

Price per night from

$654

Responds fast!
avg. 32 minutes

Price per night from

$654

(5) Excellent 

28

Elegant Designer Hamptons Retreat in Sag Harbor

Hamptons / Sag Harbor

Sag Harbor house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“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
…see more

Price per night from

$2,428

Responds fast!
avg. 2 hours 48 minutes

Price per night from

$2,428

(14) Excellent 

24

Hip & Stylish East Hampton Getaway

Hamptons / East Hampton

East Hampton house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“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
…see more

Price per night from

$409

Responds fast!
avg. 2 hours 53 minutes

Price per night from

$409

(2) Excellent 

14

Beachy Keen - East Hampton NY

Hamptons / East Hampton

East Hampton house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$650

Responds fast!
avg. 3 hours 40 minutes

Price per night from

$650

(2) Excellent 

14

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

Hamptons / Sag Harbor

Sag Harbor house

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,650

Responds fast!
avg. 2 hours 8 minutes

Price per night from

$1,650

26

Luxurious ‘Shelter Island Hideaway’ w/ Pool!

Hamptons / Shelter Island

Shelter Island house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$495

Price per night from

$495

32

NEW! Lavish Sag Harbor Home w/Pool & Tennis Court!

Hamptons / Sag Harbor

Sag Harbor house

7 14 min stay varies

  • 7 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,718

Responds fast!
avg. 14 minutes

Price per night from

$1,718

11

Beautiful and sunny hamptons home with pool

Hamptons / East Hampton

East Hampton house

4 6 7 nights min

  • 4 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,000

Price per night from

$1,000

46

Large swimming pool/Walking distance to the bay

Southampton / Hampton Bays

Hampton Bays house

4 10 14 nights min

  • 4 bedrooms
  • sleeps 10
  • 14 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary

Price per night from

$785

Price per night from

$785