50 Best Hamptons House rentals on Holiday Lettings - Apartments

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Estates East Hampton
96 properties
Estates Southampton
82 properties
Apartments Water Mill
47 properties
Vacation rentals Sag Harbor
45 properties
Bridgehampton
33 properties
House rentals Montauk
32 properties
Apartments Hampton Bays
23 properties
House rentals Amagansett
22 properties
East Quogue
13 properties
Sagaponack
9 properties
Quogue
8 properties
Wainscott
7 properties
Apartments Westhampton
5 properties

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453 Vacation rentals

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

$6000 / week

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from $900 / night

18

Vacation cottage in Montauk

Hamptons / Montauk

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $300 / night

$2100 / week

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from $300 / night

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 $5715 / night

$40000 / week

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from $5715 / night

20

Vacation home in Southampton

Hamptons / Southampton

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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 $1500 / night

$10000 - $12000 / week

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from $1500 / 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 $1000 / night

$7000 / week

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from $1000 / night

28

Vacation home in Hampton Bays

Hamptons / Hampton Bays

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Updated recently , professionally painted, this home has a cozy feel,open plan available indoors. First floor has for guests : 2 Queen size bedrooms, 2 full marble bathrooms, formal blue dining room,fully equipped and renovated marble kitchen,(stainless steel appliances …see more

from $400 / night

$2800 / week

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from $400 / night

(3) Excellent 

11

Vacation b&b in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Suitable for children age 5+
This whaling captain's house has been in my family six generations. We offer the original wing of house for weekend rental May through October. Each bedroom has a water view, and they share a dressing room/office. Enjoy the spacious porch, that includes an eating ar …see more

from $250 / night

$1500 - $2550 / week

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from $250 / night

6

Vacation home in Westhampton

Hamptons / Westhampton

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Located on the bayside of Dune Road, this property is a beach lovers paradise. Walk across the street to one of the top 15 beaches in the country; fish, swim or boat on the bay just footsteps away; or just lounge on the large deck and enjoy a . sunset. The property fe …see more

from $190 / night

$975 - $2895 / week

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from $190 / night

11

Vacation home in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets
Perfect get away in the heart of the village. Newly renovated carriage house in the historic district. 2 bedrooms, kitchen, dining room, living room, full bathroom, private yard. Located in the Historic District of Sag Harbor Village. Only 10 minutes walk to the cente …see more

from $600 / night

$3000 / week

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from $600 / night

(6) Excellent 

24

Vacation home rental

Hamptons / Montauk

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
East Hampton Rental Registry #16185 *** Please see Summer 2017 (May - October) availability, minimum stay requirements and pricing information at the end of this listing before contacting *** Thinking of spending time in Montauk? Great idea! Enjoy all the East End has …see more

from $575 / night

$3500 - $9000 / week

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from $575 / night

(3) Excellent 

71

Vacation home in Hampton Bays

Hamptons / Hampton Bays

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Swimming pool
Immaculate four bedrooms, three full baths sleeps 8-10. Full gym, pool and jacuzzi nestled away in prestigious Red Cedar Ridge. Large deck with BBQ. Fully equipped kitchen. Wi-fi internet and premium channels cable tv. Pool table, basketball and children play ground for …see more

from $800 / night

$5500 - $6200 / week

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from $800 / night

(9) Excellent 

28

Vacation home in Hampton Bays

Hamptons / 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

$3000 / week

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from $400 / night

(2) 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 turkey and stuffing balanced on her knee? Will your mother in-law fill your entire kitchen.... with herself... only to find out the Turkey she bought doesn't fit in your oven? Well it is time to escape …see more

from $400 / night

$2500 / week

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from $400 / night

7

Vacation home rental

Hamptons / East Quogue

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Air conditioning
Hello, I am a Supper Host on other sites, want to make your stay pleasurable. (`ROOM RENTAL ONLY') ...In a 3 bedroom Ranch Home...Cozy Zen Artist quite home ,Get away from all the noise or hectic life style want to try country living ...Romantic Nite sitting by the fire …see more

from $75 / night

$400 - $550 / week

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from $75 / night

(13) 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
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 enough to it all, yet r …see more

from $286 / night

$2000 - $5000 / week

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from $286 / night

11

Vacation hotel apartment in Montauk

Hamptons / Montauk

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Situated on Montauk's most pristine stretch of oceanfront real estate, Gurney's Montauk Resort & Seawater Spa is a Hampton's icon and the only four-season resort in Montauk. With five unique dining and cocktail venues, guests can enjoy a wide range of dining options, fr …see more

from $715 / night

$4999 / week

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from $715 / 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: July 21-31 (=2 weekends!) at only 10k plus cleaning and pool heat (=10.75k Total) 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 …see more

from $350 / night

$1500 - $6600 / week

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from $350 / night

13

Montauk Vacation home rental

Hamptons / Montauk

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Child friendly
This contemporary home features an amazing 4 bedrooms, 2 baths, spacious eat-in kitchen and an open living area with double height ceilings. Wrap around deck on second floor is perfect for entertaining. Only 2 blocks from ocean. This is the perfect Montauk getaway. You …see more

from $652 / night

$4564 - $5477 / week

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from $652 / night

24

Home rental in Sag Harbor

Hamptons / Sag Harbor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Escape from reality in this charming 2-bed, 2-bath Sag Harbor house, which sleeps up to 6. Located just minutes from a private beach, restaurants and shopping, this darling abode is the ideal destination for those looking to explore the Hamptons! You’ll know you made t …see more

from $449 / night

$3143 - $6293 / week

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from $449 / night

21

Sagaponack Vacation home rental

Hamptons / Sagaponack

5 10 14 nights min

  • 5 bedrooms
  • Sleeps 10
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to the beautiful and immaculate five bedroom, four bathroom house in Sagaponack, New York.  Centrally located...five minute drive from Sag Harbor, five minute drive from the ocean and our amazing beaches.  Pine hardwood floors, contemporary furnishings with all …see more

from $1715 / night

$12000 / week

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from $1715 / night

(1) Excellent 

14

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
Beautifully renovated waterfront cottage from early 1800s. Marble baths, two master suites. Sweeping waterfront lawn. 100 foot dock. Swimming, boating, grill on back deck. Beaches easy bike ride or walk. All amenities. Flat screen TVs in all bedrooms, wood burning …see more

from $267 / night

$1199 - $4999 / week

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from $267 / night

(4) 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 $2143 / night

$15000 / week

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from $2143 / night

28

Vacation home in Southampton

Hamptons / Southampton

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Welcome to your private Hamptons escape! This immaculate Southampton vacation rental house is sure to provide the perfect vacation spot for your next family getaway. Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this gorgeous …see more

from $749 / night

$5099 - $8750 / week

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from $749 / night

(1) Excellent 

28

East Hampton Vacation home rental

Hamptons / East Hampton

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 $280 / night

$1960 - $4400 / week

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from $280 / night

23

Southampton Vacation home rental

Hamptons / Southampton

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 custom Waterfront “GREEN” House, 5 bedrooms, 5 baths , CAC, hardwood floors, in-gr …see more

from $3500 / night

$19000 - $27500 / week

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from $3500 / night

(1) Excellent 

19

East Hampton Vacation home rental

Hamptons / East Hampton

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
located only 5 minutes from shops and eateries and 5 minutes to the beach. With a serene setting surrounded by mature trees, this home is a haven for ultimate relaxation and leisure. Enjoy poolside luxury by 20X40 pool in very private yard. Low Allergen Environmentchil …see more

from $500 / night

$3500 - $3900 / week

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from $500 / night

14

Southampton Vacation home rental

Hamptons / Southampton

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Ask about children
  • Ask about pets
The Space Located in Southampton less then a half a mile from the quite beaches of Peconic Bay, this house is also just a 10 minute drive to Sag Harbor or Southampton Villages. Close to ArtHampton (5 mi), Art Market (5 mi) and Hampton Classic Showgrounds (6.5 mi)! Th …see more

from $434 / night

$3034 / week

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from $434 / 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 $750 / night

$4200 - $4900 / week

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from $750 / night

27

Hampton Bays Vacation home rental

Hamptons / Hampton Bays

3 12 3 nights min

  • 3 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful Hampton Bay Home Getaway -- 2500sqft, 3br (sleeps 12) - 3 full bths & 1 half bth (HUGE Master Suite), sitting rm w/fp, living rm, dining rm, eat in kitchen, billiard room & game room -- Large Backyard w LARGE in-ground heated pool, wood burning fire pit, barbe …see more

from $795 / night

$500850 / week

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from $795 / night

18

Vacation home in Montauk

Hamptons / Montauk

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
WE OFFER ONLY MONTHLY RENTALS IN JULY AND AUGUST. Our Montauk Home is a 2 bedroom, 2 bathroom beautiful remodeled and refurbished villa. There is a queen size bed and closet in each room, the master bedroom has its on bath-toilet and shower. The living room and dining …see more

from $600 / night

$4000 - $6000 / week

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from $600 / night

7

Home rental in Southampton

Hamptons / Southampton

5 16 7 nights min

  • 5 bedrooms
  • Sleeps 16
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets
You can rent this weekly, bi-weekly or full summer season. Summer 2015 weekly rentals start at $7000/week for any weeks in June, $8750/week for any weeks in July and $9200/week for any weeks in August. You can rent for as little as a week in the summer season or monthly …see more

from $1286 / night

$9000 / week

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from $1286 / night

10

Home rental in Bridgehampton

Hamptons / Bridgehampton

5 10 14 nights min

  • 5 bedrooms
  • Sleeps 10
  • 14 nights min
  • Child friendly
Traditional two-story featuring 4 bedrooms, 3.5 bath, gourmet kitchen, Jacuzzi and heated pool. This home is a perfect summer getaway. You do not only get to enjoy your summer vacation with the beaches, good food and shopping nearby, but the house itself offers you amaz …see more

from $1435 / night

$10045 - $12054 / week

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from $1435 / 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

$3500 / week

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from $500 / 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 $1143 / night

$8000 / week

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from $1143 / night

20

Vacation home in Hampton Bays

Hamptons / Hampton Bays

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Ask about pets
Waterfront Home on Shinnecock Bay, on one of the nicest private streets in Hampton Bays, you will have use of the 2 kayaks on the bay, beautiful sunsets, and a mile away from the ocean beaches on Dune Road. We are about 2 miles from town. Great little cafe/market wal …see more

from $895 / night

$3500 - $6501 / week

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from $895 / night

11

Vacation home in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
This is a newly renovated bungalow with 2 bedrooms, full living room, eat-in kitchen, closed in and sunny porch, roomie deck with outdoor furniture (in season). It is a 5-10 minute walk to the village, fine restaurants, museums, shops, churches and temple and beach.Th …see more

from $300 / night

$1500 - $2200 / week

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from $300 / 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 $250 / night

$1750 - $4000 / week

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from $250 / night

12

Home rental in Bridgehampton

Hamptons / Bridgehampton

5 10 14 nights min

  • 5 bedrooms
  • Sleeps 10
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Bridgehampton South Traditional. 5 bedrooms (including a master both upstairs and downstairs), 4 baths, and a new kitchen with brand new marble island. The lucky tenant of this property will enjoy elegantly appointed principal rooms, further enhanced by a wonderful open …see more

from $1304 / night

$9128 - $10954 / week

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from $1304 / night

(2) Excellent 

33

Vacation home in Water Mill

Hamptons / Water Mill

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
This beautiful home is in a great location, was just renovated and is luxuriously furnished and thoughtfully appointed (including original art, and luxury linens, kitchenware and dishes new for 2016). Perfect for relaxation and entertaining, highlights include: -Lar …see more

from $1000 / night

$7000 / week

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from $1000 / night

20

Amagansett Vacation home rental

Hamptons / Amagansett

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
Classic Waterfront beach house with two private suites plus two additional bedrooms. The home is stylishly decorated, with a comfortable living room, and fully equipped kitchen. Located on the most desirable street and beach in Amagansett. This vacation rental is ideal …see more

from $2167 / night

$15167 / week

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from $2167 / night

1