50 Best Hamptons House rentals on Holiday Lettings - Apartments

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Estates East Hampton
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Estates Southampton
53 properties
House rentals Montauk
30 properties
Vacation rentals Sag Harbor
25 properties
House rentals Amagansett
12 properties
Apartments Water Mill
11 properties
Bridgehampton
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East Quogue
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Apartments Shelter Island
6 properties

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301 Vacation rentals

11

Vacation home in East Hampton

Hamptons / East Hampton

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A new construction estate in the exclusive Georgica Pond section of East Hampton brings the fabled tradition of Long Island country houses into the here and now. This gracefully proportioned gambrel home continues the proud lineage of East Hampton estates for the New co …see more

from $5,715 / night

$40,000 / week

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Responds fast!
avg. 17 minutes

from $5,715 / night

17

Cottage rental in Sag Harbor

Hamptons / Sag Harbor

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Wonderful Sag Harbor VillageWaterfront Cottage for Rent 3 bedrooms, 4 queen size beds , 1 1/2 baths, A/C, Screaming Water views, multi level Decks, Private Sand beach, with Kayaks and fire pit. All inclusive utilities, Maid service (weekly) and wonderful clear Water …see more

from $900 / night

$6,000 / week

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from $900 / night

20

Vacation home in Southampton

Hamptons / Southampton

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Child friendly
  • Pet friendly
Located in Southampton, this 6 bedroom home is 8 km from Agawam Park. Southampton 6 Bed with Pool features a grand entrance, kitchen area with marble counters, stainless steel appliances and French doors with an outside seating area. The living room offers an archway w …see more

from $1,680 / night

$11,760 / week

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Responds fast!
avg. 3 hours 8 minutes

from $1,680 / night

18

Vacation cottage in Montauk

Hamptons / Montauk

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Child friendly
  • Pet friendly
Two bedroom cottage with vaulted ceilings set on a double lot, last house on a dead end quiet road with a pond and a nature preserve across the road. Lots of outdoor living/dining space. Outdoor shower, gas grill, herb/flower gardens, washer/dryer. 5 minute walk to priv …see more

from $334 / night

$2,334 / week

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from $334 / night

13

Vacation home in East Hampton

Hamptons / East Hampton

5 12 30 nights min

  • 5 bedrooms
  • Sleeps 12
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Furnished 5 bedroom 4 bathroom home on a quiet cul de sac. In-law/nanny suite with private bathroom and living room. Viking/subzero appliances with granite countertops. Spacious deck and Porch on one acre piece of property. Great house for entertaining. Air conditioning …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

21

Home rental in East Hampton

Hamptons / East Hampton

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
Green Rock is located in the Northwest Wood section of East Hampton. The property is so well situated you will probably not want to leave it. The moon rises over the water, the sun sets in the back. Turn on the landscape lighting, open a great bottle of wine and enjoy …see more

from $900 / night

$6,300 / week

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from $900 / night

(5) Excellent 

28

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Only for the very discerning renter. It is a designer's own home. Please read rental rates before inquiring. Minimum rental is 2 weeks during High Season unless you see an availability between rentals. During the off season 1 week rentals may be possible. This elegan …see more

from $2,429 / night

$17,000 - $20,000 / week

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avg. 2 hours 51 minutes

from $2,429 / night

8

Amagansett Vacation home rental

Hamptons / Amagansett

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
Amagansett Beach House sits directly on the most beautiful beach in the world. The main floor has 3 Bedrooms with decks to beach, 2 Full Baths, and laundry room. Upstairs is the Gourmet Kitchen, Dining & Living Areas, complete with Flat screen TV. Stunning deck overlook …see more

from $1,786 / night

$12,500 / week

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from $1,786 / night

(2) Excellent 

19

Home rental in East Hampton

Hamptons / East Hampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
Location, location, location! In its ideal location on a charming, quaint cul de sac in beautiful East Hampton Village, this brand new 4-5 bedroom, 4½ bath vacation home has it all. Luxury, luxury, luxury! Its amenities include a heated swimming pool, central air-condi …see more

from $1,100 / night

$5,650 - $14,950 / week

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from $1,100 / night

(9) Excellent 

28

Vacation home in Hampton Bays

Southampton / Hampton Bays

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
Completely renovated 4 bedroom home on quiet street in Hampton Bays. In town location. Walk to shops and dining. 3.5 miles to Atlantic Ocean and 1.0 miles to Shinnecock Bay. Large property with lovely deck and furniture. Handicap accessible with bedroom and wet room o …see more

from $400 / night

$3,000 / week

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Responds fast!
avg. 2 hours 36 minutes

from $400 / night

(2) Excellent 

22

Vacation home rental

Hamptons / East Hampton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
This spacious Cape Cod design features four large, exquisitely furnished bedrooms, two full baths, stunning eat-in kitchen, sunny family/living room with fireplace, and separate dining room. A swimming pool, central air-conditioning, and high speed wireless internet acc …see more

from $900 / night

$3,250 - $10,950 / week

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from $900 / night

28

Southampton Vacation home rental

Hamptons / Southampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
***PLEASE INQUIRE FIRST (EMAIL OWNER) BEFORE INSTANT BOOKING!!.. 631 - 365 - 3828 Located east of the canal on the beautiful Peconic Bay, over 100 feet of sandy beach, walk down the shore to for food, drinks and entertainment! Beautiful, crystal clear water, 5000 sq ft …see more

from $3,300 / night

$15,900 - $19,900 / week

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Responds fast!
avg. 1 hour 41 minutes

from $3,300 / night

(2) Very Good 

10

Vacation home in East Hampton

Hamptons / East Hampton

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Air conditioning
  • Private garden
This 2 story home with 3 bedrooms and 2 baths contains a master bedroom with ensuite bathroom. It's a relaxing, quiet atmosphere. Located just 5 minutes from the town and 5 minutes from the beach. Newly furnished house is a perfect summer getaway. Naturally well lit wit …see more

from $325 / night

$2,000 / week

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from $325 / night

(14) Excellent 

24

East Hampton Vacation home rental

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Minimum two-week stay. This well-designed contemporary beach house with three bedrooms and two baths sits on an acre of blissful privacy. This vacation rental is located in East Hampton NW woods, 4 miles from East Hampton Village and 1.5 miles from Sammy's Beach. Close …see more

from $358 / night

$2,500 - $5,000 / week

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Responds fast!
avg. 3 hours 36 minutes

from $358 / night

(3) Excellent 

17

Home rental in Quogue with tennis court

Hamptons / Quogue

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
Will your mom have to sit on the end of your futon with a plate of holiday goose and stuffing balanced on her knee? Will your mother in-law fill your entire kitchen.... with herself... only to find out the roast she bought doesn't fit in your oven? Well it is time to …see more

from $400 / night

$1,500 / week

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from $400 / night

6

Vacation home in East Hampton

Hamptons / East Hampton

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
This home has been fully renovated and has been meticulously furnished. 3 bedrooms and 2 modern bathrooms Modern eat in kitchen with butcher block counter & breakfast bar Sliding doors out to large backyard 1 queen bedroom 1 bedroom with 2 fulls 1 master suite with wet …see more

from $572 / night

$4,000 - $5,400 / week

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from $572 / night

11

Home rental in East Quogue

Hamptons / East Quogue

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This 4 bedroom, 2 bathroom contemporary is just steps away from a private beach and marina. Some amenities include: New granite kitchen Cathedral great room with flat screen tv Hardwood floors Multi level decking In ground heated pool Patio furnitur …see more

from $500 / night

$3,500 / week

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from $500 / night

10

Vacation home in Southampton

Hamptons / Southampton

3 6 21 nights min

  • 3 bedrooms
  • Sleeps 6
  • 21 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
It's a 3 bedroom, 2 bath home. 2 Family room, one with a TV and one for reading and watching the sunset over Fish Cove through a large window. The master bedroom with en suite bathroom is located on one side of the house while the guest bedrooms are on the other side, …see more

from $400 / night

$2,800 / week

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from $400 / night

12

Home rental in East Hampton

Hamptons / East Hampton

8 18 7 nights min

  • 8 bedrooms
  • Sleeps 18
  • 7 nights min
  • Child friendly
13,000+/- sq. ft South of the Highway Estate in the Georgica Pond section of EH boasts 8 bedrooms- 6 En-Suite including 3 grand master suites, 3 family bedrooms & 2 staff bedrooms with separate living area. Formal Living room & Dining room, Library w wine room, large cu …see more

from $7,500 / night

$52,500 / week

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from $7,500 / night

(5) Excellent 

13

Vacation home in East Hampton

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
"The Vacationer" is a lovely, bright, white, 3 bedroom, 2 bath vacation home with a beautiful heated swimming pool. This extremely charming and appealing property features a pristine natural cedar Swedish sauna, central air conditioning, two flat screen TVs, high speed …see more

from $825 / night

$2,950 - $9,750 / week

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from $825 / night

11

Vacation home in Westhampton

Hamptons / Westhampton

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
This 3 bedroom, 2 bath ranch house is in excellent condition and is newly furnished for comfort, style, and flexibility. Sitting on 1.5 acres the house is very secluded and private and just a short drive to West Hampton Beach and many beautiful beaches and parks. There …see more

from $450 / night

$2,800 / week

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from $450 / night

(1) Good 

5

Vacation condo in Montauk

Hamptons / Montauk

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Royal Atlantic Beach Front Resort , Montauk 1 Bedroom Suite For Rent Minimum of 2 Night Stay Sleeps 4 126 S Emerson Ave, Montauk, NY 11954 ONE BEDROOM VIP SUITE: Located directly across the street from the beach. It has a private balcony facing the pool courtyard. …see more

from $200 / night

$1,400 / week

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from $200 / night

11

Home rental in East Hampton with swimming pool

Hamptons / East Hampton

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
This 5 bedroom has been added on and renovated throughout the years, and is bright and sunny with high ceilings and large window in the living room. Through the front door you will find a spacious living room, with wood burning fireplace and dining area to enjoy large …see more

from $750 / night

$5,250 / week

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from $750 / night

8

Vacation hotel apartment in Westhampton

Hamptons / Westhampton

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
Our SeaBreeze Suite sleeps up to 4 guests in two rooms - one queen bed in private bedroom and two twin sized beds in living room - as well as a small kitchen w/ refrigerator, microwave, stove top oven and coffee maker. This suite also has free wifi, premium cable and p …see more

from $140 / night

$700 - $1,000 / week

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from $140 / night

11

Amagansett Vacation home rental

Hamptons / Amagansett

4 8 21 nights min

  • 4 bedrooms
  • Sleeps 8
  • 21 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Our home, situated just north of the highway between East Hampton and Amagansett, is the ideal base for your family's vacation. The four-bedroom, four-bathroom house is bright and spacious. From the covered porch, you'll enter through the expansive living roo …see more

from $1,143 / night

$8,000 / week

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from $1,143 / night

5

Vacation home in Bridgehampton

Hamptons / Bridgehampton

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Ask about pets
Beautiful sundenched hamptons property recently renovated quiet and private yet centrally located to all ocean and bay beaches, shopping and transportation. Bike to beaches, towns of Bridgehampton and Sag Harbor. Vineyards and farm stands just up the street. Dead end s …see more

from $1,950 / night

$13,500 / week

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from $1,950 / night

23

Vacation home in Amagansett

Hamptons / Amagansett

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
Great Hamptons style in Amagansett's Bell Estate. Less than two miles to ocean beaches and one mile from the bay, close to town, has every amenity and plenty of style. Overlooks a 60-foot heated gunite pool. Details include marble baths, wide plank Walnut flooring, cath …see more

from $1,200 / night

$8,000 / week

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Responds fast!
avg. 3 hours 41 minutes

from $1,200 / night

(2) Excellent 

30

Shelter Island Vacation home rental

Hamptons / Shelter Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
WINTER SPECIAL: Stay for long weekend or Week for $999, plus utils, taxes. Any week, except holidays. Beautifully renovated waterfront cottage from early 1800s. Marble baths, two master suites. Sweeping waterfront lawn. 100 foot dock. Swimming, boating, grill on bac …see more

from $295 / night

$1,295 - $4,999 / week

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from $295 / night

(1) Excellent 

19

Vacation home rental

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SPECIALS: Please contact us for 2+ week early Bird specials. Peace and quiet awaits in this modern house on the village fringe, featuring a first floor master with walk in closet, wonderfull spa-style master bath, flatscreen TV and direct access to the pool and outdoor …see more

from $300 / night

$1,500 - $6,700 / week

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from $300 / night

(1) Excellent 

29

East Hampton Vacation home rental

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
Very stylishly renovated on .60 acre, this East Hampton property features central air, 3 bedrooms and 2 baths. Great room with fireplace and lots of sunlight. Skylights in kitchen and living room. Top of the line Sub-zero refrigerator and wine storage. A chef's dream ki …see more

from $350 / night

$1,960 - $2,900 / week

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from $350 / night

20

Water Mill Vacation home rental

Hamptons / Water Mill

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Our Southampton sunny beach luxury 4 bedroom home is ideally located near Southampton Village and area of farm fields, orchards, and wineries, and near to Coopers and Flying Point beaches. The home is set on a spacious property secluded by hedges and wildflower garden. …see more

from $1,200 / night

$7,000 / week

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Responds fast!
avg. 3 hours 11 minutes

from $1,200 / night

24

Montauk Vacation home rental

Hamptons / Montauk

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Open floorplan newly renovated close to ocean, bay beaches and montauk downs golf course 1st flr: family TV room 2 bedrooms - 2 sets of bunk beds & queen bed 1 bath w/ soaking tub 2nd flr: Open kitchen/living out to deck, 2 bedrooms - 1 king bed & 1 queen bed 1 bath …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

(2) Excellent 

7

Vacation home in East Hampton

Hamptons / East Hampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Enjoy this sophisticated, newly renovated, three-bedroom, three-bath contemporary on one of the premier lanes near Jackson Pollack's house in East Hampton. Twenty-four-hundred square feet with oak flooring throughout. Great light in the beautifully designer decorated d …see more

from $370 / night

$2,600 - $5,900 / week

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from $370 / night

19

Home rental in Amagansett

Hamptons / Amagansett

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
3 Bedrooms, 3 Bathroom, Sleeps 6+2 with A/C & HOTTUB Rental Registry # 16-2027 The Beach House is located in the Amagansett Dunes in the famous Hampton's and sits directly across the way from the most beautiful beach in the world. The main floor has 3 Bedrooms 2 Full B …see more

from $786 / night

$5,500 / week

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from $786 / night

14

Vacation private room with shared pool in Southampton

Hamptons / Southampton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 12 mi
  • Swimming pool
  • Air conditioning
Newly renovated house with nice spacious rooms with comfortable new double beds. Double occupancy room /private bathroom/entrance, queen size bed newly renovated 4 bedroom-3 bathroom home in prime Southampton location. Close to bay, beach and town. Directly across the s …see more

from $200 / night

$1,400 / week

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Responds fast!
avg. 37 minutes

from $200 / night

11

Vacation cottage rental

Hamptons / Amagansett

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Our home is right on the sand, just a block away from a beautiful, uncrowded ocean beach in one of the world's most famous resort communities. Clean and comfortable, there is an upstairs deck off the living room and a downstairs patio off the eat-in kitchen, three bedro …see more

from $275 / night

$1,925 / week

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from $275 / night

13

Vacation home in Bridgehampton

Hamptons / Bridgehampton

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Beautiful contemporary home set on 1.6 private idyllic acres. Walk to town, near beaches. Easy drive to Sag Harbor, Southampton and East Hampton. Right by Hampton Classic and Polo grounds. New designer furnishings and linens. Separate master suite with Jacuzzi and stea …see more

from $1,000 / night

$7,000 / week

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Responds fast!
avg. 2 hours 58 minutes

from $1,000 / night

37

Vacation home in Southampton

Hamptons / Southampton

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
A family place with wrap-around windows and skylights gives you the best of the Hamptons. Big beautify yard and gardens, magical garden-set pool, hot-tub and plenty of room for privacy, makes it a family dream. Backyard. 3 decks. Pool set amongst Maples and hibiscus. …see more

from $975 / night

$6,000 - $8,100 / week

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Responds fast!
avg. 3 hours 13 minutes

from $975 / night

14

Montauk Vacation home rental

Hamptons / Montauk

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
  • Private garden
DIAMOND BEACH HOUSE ,IS LOCATED IN THE CULLEN SHORES AREA.ONE BLOCK, TO PRIVATE BEACH . HOME HAS TWO DECKS, NEW APPLIANCES ,CEILING FANS THREW OUT. .AND AC IN BACK ROOM SLEEPS 9 .OUTDOOR SHOWER. PRIVATE BACKYARD .THERE IS THE CROWS NEST LOOKOUT, OF THE SOUND .AMAZING SU …see more

from $550 / night

$3,500 / week

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from $550 / night

28

Water Mill Vacation home rental

Hamptons / Water Mill

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Exquisite 50 foot driveway, handmade iron gated property, affording total privacy, 2 acres exquisite landscaping, flowers, vegetable garden, 2 waterfalls, gardens, stream, pond, pond beach, 30 x 40 gunite swimming pool with Rose Arbor, fruit orchard, Outdoor Kitchen & …see more

from $715 / night

$5,000 / week

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from $715 / night