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Long Island Holiday Vacation with Pools

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    Travellers to Long Island are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    157 Matching Rentals in Long IslandView all 437 rentals
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    Beautiful Classic North Fork Home, wrap around porch, pool, walk to beach1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Ground floor sunlit apt. in great area!1 / 16
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Chic Bridehampton Pristine Designer Home + Free Pool Heating!1 / 20
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Village Fringe glassy Modern with Pool and Tennis1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Secure Parking
    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 24, 2017
    My family was looking for a quiet house to relax in a beautiful setting, and we had just this house. This sunny, bright, clean and pleasant...most of all, luxurious house with...
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    About this property
    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 shower. The kitchen, the...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Hip & Stylish East Hampton Getaway1 / 24
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 23, 2017
    My husband and I loved staying here with our two teenage sons. We visited from the UK and spent 4 nights in Manhattan before driving over to the Hamptons. We loved the buzz and...
    Reviewed September 6, 2016
    We loved the house and had a great stay in the Hamptons.The house is in a very quiet and beautiful environment, surrounded by trees, only a 10 minute drive max to East Hampton...
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    About this property
    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 enough to it all, yet...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 bedroom Private Family Get Away1 / 45
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Children's Pool
    • Washer
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2018
    The kids loved the pool! beaches are only a few miles away. We needed a few items and were happy to know that their were a shopping mall right around the corner!
    Reviewed March 5, 2018
    Carrie was a wonderful host and left my crew some champagne and cookies for the weekend! We used the house for a bachelorette party in the Hamptons in August and It was perfect...
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    About this property
    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 skylights includes open kitchen,...
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    Westhampton Beach, Hamptons 11978
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    July - August 2017. Open floor plan, modernist house in the Village of Springs1 / 5
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2017
    Beautiful open plan modernist home, close to both East Hampton and Amagansett towns but away from the hub-bub in country-like Springs. The house has a great pool and an amazing...
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    About this property
    Superbly designed by its owners, this dwelling boasts the elegance and sobriety of a minimalist painting. Yet, it remains very warm and inviting. The house sits on a wooded acre, across the road from a 140 acre reserve. The 2,500 sq. ft. space offers 2 bedrooms, 2 bathrooms, living room with wood...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 5, 2018
    Very nice, spacious apartment. Tranquil surroundings. Small pebble stone beach with a serene atmosphere. Beautiful sunsets. Very bucolic. Communication with the owner was...
    Reviewed February 11, 2018
    Great accommodations, beautiful view, FANTASTIC SUNSETS, what’s not to like!As a repeat customer staying here in Spring, Summer and Fall I give stars.
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    About this property
    Overview: Waterfront Water's Edge suite, Suite C-204, accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. Quoted rental rates include all taxes, I do not charge resort fees...
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    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3BR/2BA- Private Heated Pool Steps to Moriches Bay1 / 21
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Grill
    • Patio
    • Washer
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 1, 2018
    Christine's house was perfect for our family stay in the Hamptons after a busy week with a family wedding in Brooklyn/New York. The children really enjoyed the pool and the...
    Reviewed June 16, 2015
    I welcomed my friends from Germany to the U.S. What made the stay super sweet for them and for myself was this rental. It had everything we needed. I'm a local in Westhampton...
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    About this property
    Easy summer living at this bright contemporary ranch located steps from Moriches bay in Westhampton/Remsenburg. Open kitchen- dining area, living room with fireplace, 3 bedrooms, 2 baths, central air conditioning, and a private yard with a heated swimming pool. Located on a small quiet block,...
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    Remsenburg, Hamptons 11960
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Serene & Private East Hampton Summer Rental w/pool1 / 19
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 27, 2016
    The owner was attentive and so lovely pointing out the all important designer shoe sale to my daughter and I (yes we did go and get a pair each haha). The house is larger than...
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    About this property
    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 Environmentchildren welcomenon smoking...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Cherry Grove Oceanfront with Heated Pool1 / 23
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Patio
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 16, 2016
    My partner and I stayed at this house in the off-season in October. We had such an awesome stay. The homeowners were super friendly and accommodating. Anything we needed they...
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    About this property
    THE MOST DESIRABLE LOCATION IN CHERRY GROVE. NOW TAKING RENTALS FOR 2019 Come join us in our fabulous get-a-way from the hustle and bustle of everyday life. This incredible 'gay' oceanfront property is nestled in Cherry Grove, Long Island which hosts beautiful white sandy beaches. Sleep to the...
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    Location Information
    Cherry Grove, Fire Island 11742
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Post Modern Quaint Home Near  Beach1 / 142
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • DVD Player
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This house exactly served our needs for a family getaway for ourselves, our two adult daughters, their husbands, and two grandkids -- a newborn and a 2-year-old. There was...
    Reviewed September 4, 2017
    Highly recommend this house. Clean, large enough for to fit our 2 families very comfortably. Owner was very responsive.
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    About this property
    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 entertainment. Five min...
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    Location Information
    Hampton Bays, Southampton 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning contemporary house is set on two private acres in the near Northwest Woods. Bright, white filled with sunlight, this four bedroom, two and a half bath multi-level home has soaring cathedral ceilings on the main level, large king master bedroom suite with private deck, TV, new bath...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Bridgehampton Village Beauty1 / 26
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 2018
    Beautifully decorated and spacious house. The perfect summer getaway! Everything from the pool, to the fireplace outside, and everything else made my stay enjoyable and super...
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    About this property
    Our home is a beautiful and serene oasis in the heart of Bridgehampton Village. A gourmet kitchen, three dining areas, an indoor and outdoor fireplace, four separate sitting and relaxation areas, a pool house with a bar and large screen tv. The house is a place where multiple generations can...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Hamptons private beach front home + pool1 / 17
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Ocean Views
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly refurnished and upgraded Hamptons Beach House. Amazing bay views from every room. Heated pool and private sandy beach. Ideal for large families. Swim in the bay or your own pool. This home is on the border of Shinnecock Hills and Hampton Bays making it very desirable due to its...
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    Location Information
    Hampton Bays, Southampton 11946
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Hamptons Retreat  *Pool & Spa*1 / 28
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Centrally located and completely renovated! Lovely two story Victorian home - 3 bedrooms, 2 full baths with central air. The perfect place to rejuvenate and indulge. Unwind in the hot tub among hydrangeas and roses. Breakfast on the sun porch. Dine at one of many Zagat rated restaurants. Walk...
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    Location Information
    East Quogue, Hamptons 11942
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Spacious Home with Pool in Heart of the Hamptons!1 / 33
    (2)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Grill
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 19, 2016
    All I can say is WOW! Patrick's home is a dream!! Patrick has done an amazing job decorating this home. It was so comfortable inside and out from tasteful furnishings, a...
    Reviewed July 18, 2016
    This has it all, in a Perfect location, convenient to Hamptons shopping, beaches, restaurants, with the quiet of a private retreat. The house has large open rooms for...
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    About this property
    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: -Large open concept family room...
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    Location Information
    Water Mill, Hamptons 11976
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    • Washer
    • Parking
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, barbecue grill, sand volleyball...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    7 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Washer
    • Patio
    • Cable/satellite TV
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Lauren Berger Collection is proud to be recognized as one of the best Vacation Rental companies in the world by the best, The Vacation Rental Guide. The idyllic setting of this spectacular, stately waterfront home in the picturesque village of West Hampton Beach makes it perfect for...
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    Westhampton Beach, Hamptons 11978
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 20
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    Elegant Designer Hamptons Retreat in Sag Harbor1 / 28
    (5)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 elegant 6000 square foot home...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 12
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    Beachy Keen - East Hampton NY1 / 15
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Patio
    • Housekeeping Included
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2016
    We stayed for four days. The house is very nice and just as depicted in the photos. Pam was very gracious and very accommodating. She was very flexible with arrival and...
    Reviewed August 4, 2016
    Very cute and homey house, great hosts and a good location in the Hamptons. Close to Sag Harbor and East Hampton and close to the water. The pool is really nice and clean and...
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    About this property
    Spend time relaxing by the heated pool or enjoying the nearby beautiful ocean and bay beaches of the Hamptons. This charming air-conditioned home is sited on a privately landscaped half acre property. An open light filled great room floor plan with double height ceiling. Ample decking for lounging...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Westhampton Beach Village  LONG ISLAND New York1 / 15
    (3)Terrible
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Grill
    • Porch
    • Patio
    • Shared Garden
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home secluded area. Just renovated. Near everything ocean and beaches. Big backyard. Sports play. Outdoor kitchen-Pool-outdoor shower-circular driveway-6 cars parking. Huge kitchen island and bar sink. 3 masters suites second floor. 3 others large sizes 1st floor. Finished basement too....
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    Location Information
    Westhampton Beach, Hamptons 11978
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    Luxury Hamptons Quogue Village 4BR Modernist Retre1 / 30
    (3)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 3, 2017
    We just found out about this and it's a wonderful property. The town of Quogue houses some of the most successful people inNew York and is astronomically expensive.The Quogue...
    Reviewed August 3, 2014
    I recently stayed at the Luxury Hamptons Quogue Village 4BR Modernist Retreat with my girlfriend, her sister's and brother in law, and had the best time. The house is new and...
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    About this property
    Quogue Village Modern 6BR, 4WC recently renovated in rustic modern style. Light and airy with skylights and large windows and doors. Huge chef's kitchen boasts 6 burner range and double sinks. Expansive 40 ft pool, 8 person hot tub, 1.3 acres on quiet wooded cul de sac, and Quogue Village beach...
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    Location Information
    Quogue, Hamptons 11959
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Private Garden
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful house with an independent studio close to railroad station Beautiful water view. Fishing and paddle boat. Kitchen facilities neat people only We can offer extra bedroom. Shower and pool spa also. Near shopping and restaurants. Internet Wifi and TV room. Deck and Barbeque. You have to see...
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    Location Information
    Kings Point, Long Island 11023
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    East Hampton Family Retreat with Cottage1 / 41
    (5)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2017
    Relaxing weekend. Leanne has very thoughtfully planned out the house, there are grills, gas fire pits, a roof decks. The furniture is very comfortable. The floor plan is great...
    Reviewed August 6, 2015
    The best vacation ever! The main house, the cottage, the pool, the kitchen, the cabana, everything met or exceeded our expectations. The kitchen was stocked with everything...
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    About this property
    2 night minimum weekends, 3 night minimum all holiday weekends. Hot tub and pool are closed for the winter season.. Hot tub closes Dec. 1st., 2018 Pool closes Oct. 1st. 2018 Please note! The base rates listed are off season ONLY, higher Memorial Day to Labor Day. Beautiful wooded property and...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming, private, 2 story cottage with outdoor balconies. 'Treehouse' feel with great wooded views. Queen bed, one loft bed, full bath, hardwood floors on second floor. Sitting area, twin bed on first floor with washer/ dryer. Covered balcony with gas fire ring, warm and cozy! Amazon / Netflix...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    About this property
    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. This suite features an open...
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    Montauk, Hamptons 11954
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Very Private and Tranquil  House in wooded estate.1 / 20
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
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    Reviewed September 25, 2017
    Let me share my impression in short: very convenient location, exceptional cleanliness in rooms, outdoor pool, beautiful plot, very friendly host Lydia. There is not better...
    Reviewed August 15, 2017
    Wonderful casa tua! Very welcoming , beautiful house , gracious hosts , great breakfast and beautiful backyard and pool.Highly recommend!
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    About this property
    This well-appointed and maintained 2,200 sq.ft., 4 bedroom, 3 bath Contemporary has a bright sunlit breakfast area directly off the gourmet kitchen, Situated on a sprawling manicured acre with a 20x40 sparkling swimming pool and directly across the street from the fascinating Peconic Bay with...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely home on prime BH North Street, with privacy and lots to do around. Gourmet kitchen with good knives and all clad. Garden is organic with lots of herbs and flowers. There are 3 whirlpool baths. One king. Size bed is sleep number. Owners want you to enjoy!
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Westhampton Waterfront 6 Bedroom Secluded 3 Acre E1 / 13
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • DVD Player
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    • Waterfront
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    Pet friendly
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    About this property
    The Perfect Getaway Westhampton Waterfront Secluded Estate Drive along this Hamptons vacation rental properties private stonewalled 800 ft driveway and into what Hampton style living is all about. This home is located on three acres of beautiful waterfront property in Westhampton. With...
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    Westhampton, Hamptons 11977
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    LUXURY HAMPTON ESTATE 4  PRIVATE RENTALS W/TENNIS,1 / 88
    (7)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 19, 2015
    Mark was really wonderful to work with and very friendly. He made sure to meet us at the house and personally give us a tour/show us the many amenities the house had available...
    Reviewed August 19, 2015
    Mark was a very fun and gracious host, meeting us upon arrival to provide a full tour of all the amenities (the house has many!) from his vintage toy collection to where the...
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    About this property
    ALL THE LUXURY IN AND OUT, WITH AMENTIIES UNHEARD OF IN ANY OTHER HAMPTON ESTATE RENTAL: This is strictly a private rental. preferably for families or responsible groups. We have 6 bedrooms and a separate 2 l bedroom pool house. Note the pool house is 'campy' and fun no where near the...
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    Westhampton, Hamptons 11977
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Sauna
    • Housekeeping Included
    • Hot Tub
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    Pet friendly
    Kid friendly
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    About this property
    Fabulous Southampton Luxury Mansard completely private and renovated in 2018 with amazing entertaining spaces and Beautiful 20' x 40' Heated Gunite Pool. Two outdoor fire pits, Sonos music inside and out. 4 Bedrooms with (5) queen beds and (1) King Bed Master Suite. 2 miles to Southampton Village...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    East Hampton/ Sag Harbor, 8 Acres, Pool, Tennis Ct, Hot tub, Sauna1 / 16
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 30, 2017
    This location was just perfect for our family. There was so much to do and enjoy. We were looking for a spot that satisfied my athletic sons, my mellow daughters and our three...
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    About this property
    8 ACRES: Rare privacy in East Hampton, NY nestled on 8 acres, Northwest pine tree forest, PRIVATE TENNIS, miles of walking trails. Truly a getaway to nature yet 3 minutes to Sag Harbor and East Hampton, shopping, and restaurants. 1 mile to glorious sunsets bay beach... ideal for little children....
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    East Hampton, Hamptons 11937
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Hydrangeas and Roses when you...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape from everything at a private beach with gorgeous sunsets or dive into the backyard pool for a refreshing swim. Bright, open floor plan features a new kitchen and ample decking with an outdoor shower. Featuring 3 bedrooms and 2.5 brand new bathrooms. Wood burning fireplace in main living...
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    Springs, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    'Pennies From Heaven'1 / 25
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 21, 2016
    House and groundsI stayed at this property with my boyfriend and another couple for a long weekend. It was great!! It was a super easy drive from the city and upon arrival, we...
    Reviewed June 12, 2016
    We had a terrific stay with our family at this prefect private get away that offers it all . Set on a private cul de sac for peace and quiet yet minutes from town, shopping...
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    About this property
    Summer house that has it all! This 4 BR/3 Bath newly updated property, sits on a 1/2 acre lot with a newly lined in-ground pool with Trex decking surround and features an open concept main living space, entertainment space, high end finishes and tons of privacy. Local Realtors have identified this...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Southampton Waterfront- Beach Home- 2 kayaks!1 / 28
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 12, 2018
    Spacious and well maintained home. Wonderful and responsive owner.Especially loved the lofted ceiling, great room, huge kitchen island, master suite with big walk-in closet and...
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    About this property
    ***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 custom Waterfront “GREEN”...
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    Southampton, Hamptons 11946
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, cathedral ceilings, sound system,...
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    Amagansett, Hamptons 11930
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sag Harbor designer home, Chef's kitchen & one block from the water1 / 14
    (2)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 12, 2017
    We loved everything about this place. From the outdoor fire pit to my elderly parents having the time of their lives. Everything was impeccable. We look forward to returning...
    Reviewed March 23, 2017
    Our family enjoyed a great week in Sag Harbor and wonderful accommodations. The house is as advertised, nicely and warmly decorated with beautiful pool and outdoor grounds. The...
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    About this property
    For a truly authentic experience of Sag Harbor, stay at this delightful 5-bedroom, 2-bathroom designer's home with oversized heated pool and ideally situated just 2 blocks from Long Beach . With 2,800-square feet of living space and enough sleeping accommodations for up to 10 guests, this residence...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    East Hampton Luxury Home  PERFECT FOR FAMILIES1 / 34
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 seats 8, fireplace with...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    East Hampton Dream House 'Serendipity' - Great Buy1 / 7
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    My father and I stayed here for a week at the end of this past September. I can say without a doubt we will absolutely be booking another stay here in the future! Even though...
    Reviewed June 25, 2017
    My wife and I stayed at this lovely place last week. Our two sons and their girlfriends also stayed. We had a fantastic time. The heated swimming pool was absolutely fabulous...
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    About this property
    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 double height living/dining...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 furniture and gas grill Linens One car garage MINIMUM...
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    Location Information
    East Quogue, Hamptons 11942
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    East Hampton Classic1 / 22
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 28, 2017
    We had a wonderful time at the house. The facilities were excellent, and John made an extra effort to accommodate our needs for Christmas dinner preparation. We particularly...
    Reviewed October 14, 2017
    My wife and I stayed here for four nights. The house was very nice. The pool was a nice extra; even though we didn't use it. The location was secluded and very serene. John, the...
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    About this property
    Located down a winding drive in the town of East Hampton our four bedroom home was constructed in the classic Hampton's style with cedar shingles and white wood trim. Sited on an acre and a half in the Northwest Woods, beautifully landscaped and private with close to 20 acres of reserve land...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated five bedroom/three bath house with pool has been completely updated inside and out with all new furnishings and linens! Cell phone reception! Situated on one acre next to a reserve, this two story bright, white contemporary offers easy indoor/outdoor living for its guests....
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    East Hampton, Hamptons 11937
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New! Last minute cancellation / shorter periods available July and August. Light, Bright And Completely Renovated. Spacious Modern Contemporary Home. Offers 5 Bedrooms, 3.5 Baths On Over 2 Private Acres. Enjoy Heated Pool, Hot Tub And Tennis, Foosball And Ping Pong. Great Room W/Fireplace And Wall...
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    East Quogue, Hamptons 11942
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 steam shower. 3 Additional...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ocean Front Cottage Montauk for rent1 / 50
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Air Conditioning
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    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 21, 2018
    We were there to attend the US Open final day. It’s a reallly picturesque spot. The cottage has all you would need for a short stay getaway for 4. Linger stays might be a little...
    Reviewed August 31, 2017
    This was a small cottage with a spacious feeling. The ceilings were high and it was the perfect size for 4 people. We were able to cook breakfast everyday and it had most of the...
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    About this property
    It is a 1000 sq foot cottage which is private, surrounded by hedges with the master suite, kitchen, main room and decks all over looking the ocean. Very warm and cozy, with wood beam ceilings, modern kitchen with all new appliances including dish washer. This cottage has been in our family for...
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    Montauk, Hamptons 11954
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely 4 bedroom home backs to preserve and is located just north of the village with an open floor plan and wonderful light and high ceilings throughout. Main floor has guest bedroom and bath, living room with fireplace and double height ceilings, separate dining area and eat-in kitchen, which...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand New Chic Saltwater Dark Bottom Pool with Tanning Ledge! Whisper quiet retreat for all seasons in updated contemporary saltbox in East Hampton's NW Woods. Close to beach and charming EH and Sag Harbor! Rental contract required. RR # 161918 Also has wood burning fireplace and firewood...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Chic and Modern Beach retreat with heated Pool1 / 16
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
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    • Balcony
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    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 4, 2016
    This house has everything you need and is perfectly located. It is not far from Sag Harbour in a quiet area. Close to marina for kayaking and stand up paddle boarding. With...
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    About this property
    Privately situated on a park-like landscaped grounds, this classic 2 story French cottage was completely renovated for modern comfort and indoor/outdoor summer entertainment. This delightful house features an open-plan living room with fireplace, dining room, a gourmet kitchen with stainless...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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