50 Best Hamptons House rentals on Holiday Lettings - Apartments

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Estates East Hampton
77 properties
Estates Southampton
70 properties
House rentals Montauk
31 properties
Vacation rentals Sag Harbor
29 properties
House rentals Amagansett
14 properties
Apartments Water Mill
12 properties
Bridgehampton
11 properties
East Quogue
10 properties
House rentals Westhampton Beach
10 properties
Springs
9 properties
Apartments Shelter Island
6 properties

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342 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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avg. 17 minutes

from $5,715 / 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

26

Vacation home with swimming pool in Hampton Bays

Southampton / Hampton Bays

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
For adults over 26 years kids OK please INQUIRE first with your details for availability min. 2/3 nights depends date. EXTRA to price on screen at CHECK- IN: 180$ cleaning fee/stay ,refundable security deposit 500$-3.5K (depend dates,number of guests and age range) sec …see more

from $600 / night

$4,000 - $6,193 / week

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from $600 / 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

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

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

29

Vacation apartment in East Quogue

Hamptons / East Quogue

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 7 mi
  • Child friendly
  • Pet friendly
This is a very cozy house with lots of trees around. Only 7 minute drive to the beach. The house has Two bedrooms, one queen bed in the master bedroom, a trundle bed in the second bedroom. Also a comfortable sofa bed in the living room. There is plenty of space in the b …see more

from $165 / night

$1,750 / week

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avg. 1 hour 13 minutes

from $165 / night

(14) Excellent 

24

East Hampton Vacation home rental

Hamptons / East Hampton

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • 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 $429 / night

$3,000 - $5,000 / week

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avg. 3 hours 28 minutes

from $429 / night

9

Hampton Bays Vacation home rental

Southampton / Hampton Bays

3 4 13 nights min

  • 3 bedrooms
  • sleeps 4
  • 13 nights min
  • Child friendly
  • Air conditioning
  • Private garden
BEAUTIFUL BAYFRONT HOUSE AND SEPARATE GUEST COTTAGE !! Near all, restaurants, movie theaters, town, 7/11,Star Bucks, Dunkin Donuts TRAIN, fishing, ocean beaches, swimming and all water activities. BBQ, eat on the deck watch the boats go by. Private fenced in yard. …see more

from $200 / night

$2,800 / week

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from $200 / night

(1) Very Good 

10

Vacation home in Water Mill

Hamptons / Water Mill

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Modern 3+ Bedrm/2.5 Bathrm with 70' WATERFRONT in luxurious Water Mill. Leave your car home! 2 Minute stroll to Village for bagels in the morning and Suki Zuki sushi (restaurant) in the evening. Bike/Walk to Ocean/Beach (1.5 Mile). 5 minute walk to Luxury Hampton Jitney …see more

from $680 / night

$5,000 / week

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from $680 / night

(3) Excellent 

19

Vacation home in Westhampton Beach

Hamptons / Westhampton Beach

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Located on the bay side of Dune Road on a scenic peninsula and surrounded by water, this contemporary is a beach lovers paradise. It's a short walk to the great Westhampton Beach, one of the top 15 ocean beaches in the country; a 5 minute drive to the village; or you ca …see more

from $150 / night

$950 - $3,250 / week

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from $150 / night

8

Vacation hotel apartment in Westhampton

Hamptons / Westhampton

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • 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 $150 / night

$700 - $800 / week

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avg. 1 hour 42 minutes

from $150 / 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 $350 / night

$1,500 - $6,500 / week

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from $350 / night

23

Vacation home in Amagansett

Hamptons / Amagansett

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • 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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from $1,200 / night

27

Hampton Bays Vacation home rental

Southampton / 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 $655 / night

$4,585 / week

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from $655 / 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

6

Villa rental in Remsenburg

Hamptons / Remsenburg

5 9 5 nights min

  • 5 bedrooms
  • sleeps 9
  • 5 nights min
  • Child friendly
  • Ask about pets
19th Century house on 3 acres of gardens and fields. Traditional styling has been infused with modern touches and updates. Cook's professional kitchen, central air conditioning, jacuzzi, steam shower, heated swimming pool, internet and multi-room music system. Close …see more

from $1,300 / night

$7,950 / week

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Responds fast!
avg. 34 minutes

from $1,300 / night

22

Vacation home rental

Hamptons / Westhampton Beach

4 6 14 nights min

  • 4 bedrooms
  • sleeps 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful waterview home includes 4 Bedrooms and 2 Bathrooms. It has gorgeous waterviews overlooking large upper and lower decks with large inground pool and outdoor shower with dressing area. Newly renovated kitchen with solid surface counter tops and top of the l …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

24

Home rental in Amagansett with swimming pool

Hamptons / Amagansett

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
RR#16-992 4/09/2018 Heading to the Hamptons? Then go ahead and book this 6-bedroom, 5.5-bathroom vacation rental home in Amagansett with sleeping for 12! Great for larger families, friends, or couples seeking a beach getaway, this will serve as the perfect home base fo …see more

from $740 / night

$5,180 / week

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Responds fast!
avg. 32 minutes

from $740 / night

24

Water Mill Vacation home rental

Hamptons / Water Mill

6 14 2 nights min

  • 6 bedrooms
  • sleeps 14
  • 2 nights min
  • Nearest beach 6 mi
  • Swimming pool
  • Child friendly
This 3500 sq ft Hampton's styled home has a large light filled living room with fireplace and sliding glass doors to the expansive deck with heated pool. The open floor plan makes this home perfect for entertaining. This home is situated on .75 of an acre of property th …see more

from $675 / night

$4,725 / week

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from $675 / night

19

Vacation home rental

Hamptons / Bridgehampton

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Bridgehampton Blue House RATES INCLUDE THE FOLLOWING: Electric consumption, cable TV & wi-fi, propane consumption, telephone, trash removal, lawn & pool service and pool heater set to 85 degrees between Memorial Day and Labor Day* PLEASE NOTE THAT THIS HOME IS ON THE …see more

from $500 / night

$4,500 - $5,500 / week

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avg. 1 hour 3 minutes

from $500 / night

9

Vacation home rental

Hamptons / East Hampton

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Child friendly
Enjoy this stylishly decorated contemporary with three bedrooms and two bathrooms, featured in the August 2014 issue of AVENUE BEACH Magazine. The resort-like pool area invites you to relax and enjoy. Located within an easy distance of the villages of East Hampton, Amag …see more

from $1,500 / night

$11,000 / week

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from $1,500 / night

26

Vacation home with golf nearby in East Hampton

Hamptons / East Hampton

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Enchanted Garden setting is the perfect way to describe this Cottage that is walking distance to one of the most Beautiful Private Bay Beaches in the Hamptons! This immaculate home has three Bedrooms & two renovated custom designed bathrooms. You will be surrounded by H …see more

from $2,200 / night

$12,500 / week

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avg. 34 minutes

from $2,200 / night

(4) Excellent 

71

Vacation home in Hampton Bays

Southampton / Hampton Bays

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • 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

$6,000 - $6,700 / week

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from $800 / night

(4) Excellent 

45

Westhampton Beach Vacation home rental

Hamptons / Westhampton Beach

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
Private, spacious 5 bedroom, 3 bath home w/yard for relaxing, entertaining & sports. In deck heated pool w/safety fence. Huge kitchen, premium cable, wi-fi, fireplace. Neighborhood ideal for families - long walks, bike rides, wildlife watching. Large great room with sky …see more

from $350 / night

$2,450 / week

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Responds fast!
avg. 1 hour 42 minutes

from $350 / night

41

Vacation home in Montauk

Hamptons / Montauk

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
One large fishing cabin from the 20's has been redesigned and renovated with upcycled materials for contemporary loft style living with a Mediterranean touch. 3 bedrooms, 2 bathrooms (claw foot bathtubs), and a loft style common room with cathedral ceiling. Concrete flo …see more

from $600 / night

$4,200 / week

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from $600 / night

20

Vacation villa with tennis court in Water Mill

Hamptons / Water Mill

7 10 14 nights min

  • 7 bedrooms
  • sleeps 10
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
This beautiful estate home in Water Mill, New York borders the prestigious Matt Lauer's 40 acre horse farm with distant ocean views. This estate features 7 bedrooms with 7 en suite bathrooms, 2 1/2 baths, two master bedrooms. There are five full masonry fireplaces, po …see more

from $2,857 / night

$25,200 / week

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from $2,857 / 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

29

Vacation home in Sag Harbor

Hamptons / Sag Harbor

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
  • Air conditioning
The New York coast awaits at this Sag Harbor 4-bedroom, 3-bathroom vacation rental house with additional sleeping arrangements with 2 sofa beds in the den - the perfect destination for up to 10 guests! This home boasts one of the best locations with walking access to pr …see more

from $600 / night

$4,200 / week

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Responds fast!
avg. 32 minutes

from $600 / night

11

Home rental in East Hampton with swimming pool

Hamptons / East Hampton

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • 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

(5) Excellent 

22

East Quogue Vacation home rental

Hamptons / East Quogue

8 8 2 nights min

  • 8 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
Beautiful two level 4,100 sq. ft. home in East Quogue is sure to accommodate all your summer get away needs. If you enjoy spending quality time together our home provides a large backyard with an in-ground heated pool, and a new BBQ. Than come hang out inside in our g …see more

from $1,200 / night

$8,400 / week

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from $1,200 / night

(2) Excellent 

30

Shelter Island Vacation home rental

Hamptons / Shelter Island

4 8 15 nights min

  • 4 bedrooms
  • sleeps 8
  • 15 nights min
  • 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 / week

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from $295 / night

25

Vacation home in Hampton Bays

Southampton / Hampton Bays

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Walk to Shinnecock Bay and enjoy an afternoon swimming and lounging on the private beach. The ocean at Ponquogue Beach is but 1.3 miles away, where you can play in the sand and soak up the picturesque views. This beautiful 3-bedroom, 2.5-bathroom vacation rental home sl …see more

from $250 / night

$1,750 / week

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avg. 35 minutes

from $250 / night

(14) Excellent 

26

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. 1 hour 22 minutes

from $400 / night

34

Vacation home with swimming pool in Westhampton Beach

Hamptons / Westhampton Beach

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Visit one of the most desirable places in the world at this private 5-bedroom, 3-bathroom vacation rental home on Moriches Bay, Westhampton. This 3,200-square-foot castle on the bay comfortably accommodates 10 guests and is located at the end of a private cul-de-sac, of …see more

from $1,000 / night

$7,000 / week

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Responds fast!
avg. 32 minutes

from $1,000 / night

(1) Excellent 

29

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 $350 / night

$1,960 / week

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from $350 / night

(1)  

24

Vacation home with swimming pool in East Hampton

Hamptons / East Hampton

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Immerse yourself in all that East Hampton has to offer at this stunning 4-bedroom, 3-bathroom vacation rental house that comfortably sleeps 10. Situated on 2 acres of fenced land with a playground, lush grass, private hot tub and 50-foot pool with 10 chaise lounge chair …see more

from $560 / night

$3,920 / week

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avg. 35 minutes

from $560 / night

26

Vacation home rental

Hamptons / East Quogue

5 10 4 nights min

  • 5 bedrooms
  • sleeps 10
  • 4 nights min
  • Child friendly
Summer getaway located in the heart of beach country. 3,100 square foot private & spacious house with 5 bedrooms, 3 1/2 baths, 20x40 pool (w/new heater!), hot tub and tennis court situated on a full acre in the most desirable section of East Quogue. When you walk in t …see more

from $1,025 / night

$6,400 / week

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Responds fast!
avg. 1 hour 10 minutes

from $1,025 / night

7

Home rental in Bridgehampton

Hamptons / Bridgehampton

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Child friendly
This cozy furnished country-style farmhouse sleeps ten people comfortably and is minutes to ocean or bay beaches, shopping, and restaurants. The house sits on over an acre of land adjacent to 1,000-acre Long Pond Reserve. Out back is a wooden deck, an in-ground pool, …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night

(1) Excellent 

36

Home rental in East Hampton

Hamptons / East Hampton

5 11 7 nights min

  • 5 bedrooms
  • sleeps 11
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This beautiful summer home sits on an acre property only 3 years old and newly painted and furnished by Perter Andrews. It has a salt water heated pool, new cedar children's jungle gym with swing set, elevated ceder deck, dining room that seats 10, Eat-in kitchen that …see more

from $1,429 / night

$10,000 / week

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from $1,429 / night