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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.
    203 Matching Rentals in Long IslandView all 518 rentals
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    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beautiful Classic North Fork Home, large porch, pool, Jacuzzi, walk to beach1 / 19
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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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    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
    • Patio
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    • Washer
    • 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
    Stunning Home w/Modern, New Kitchen. Walk to Everything in East Hampton Village!1 / 13
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 1, 2015
    It was a delightful experience to stay at “The Vacationer” during my recent trip to East Hampton. The house is located in a very quiet neighborhood and is walking distance from...
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    About this property
    'The Vacationer' is a lovely, bright, white, 3 bedroom, 2 bath vacation home with a beautiful heated swimming pool. This extremely charming and appealing property features a pristine natural cedar Swedish sauna, central air conditioning, two flat screen TVs, high speed WiFi, and a new stainless...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    'Pennies From Heaven'1 / 25
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Washer
    • Air Conditioning
    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
    Luxury Hamptons Vacation Home w/NEW Pool, Tennis Court, Hot Tub1 / 32
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
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    • Washer
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    • Wi-Fi
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS TURNKEY PROPERTY HAS SOME OF THE BEST AMENITIES IN THE HAMPTONS. MANY OF THE IMPROVEMENTS WERE COMPLETED IN THE LAST TWO YEARS! Compare us with other area properties: - FRESHLY PAINTED EXTERIOR IN 2017 - HOUSE IS FULLY UP TO CODE, INCLUDING EGRESS WINDOWS IN LOWER LEVEL BEDROOMS FOR YOUR...
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    Quogue, Hamptons 11727
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Chic and Modern Beach retreat with heated Pool1 / 16
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Washer
    • Wi-Fi
    • Balcony
    • Grill
    • Air Conditioning
    • 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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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Parking
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 groups. There is one half...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    Luxury Hamptons Quogue Village 4BR Modernist Retre1 / 30
    (3)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • 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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    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • 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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    Location Information
    Hampton Bays, Southampton 11946
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
    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
    • Internet Access
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    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
    Beech Tree Cottage1 / 15
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Shared Garden
    • Wi-Fi
    • Outdoor Dining Area
    • Parking
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 18, 2018
    With a full kitchen and living room, outdoor terrace and perfect so-close-you-can-walk-to-town setting, you will be so happy you snagged this spot! I’m picky, and I know what’s...
    Reviewed August 7, 2016
    Spent two nights at Beech Tree with my husband and grown son. Cottage is located within walking distance of town, in a nice residential neighborhood. Kitchen is well stocked, we...
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    About this property
    Beech Tree Cottage is a charming two-bedroom, one-bath guest cottage conveniently located in the historic district of Sag Harbor, NY - a 5-minute walk along the waterfront to Main Street and the center of the village. The beach is a short drive or bike ride away. The owners are full-time residents...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Beachy Keen - East Hampton NY1 / 16
    (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
    East Hampton/Sag Harbor Village Fringe1 / 26
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    • DVD Player
    • Parking
    • Patio
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 25, 2018
    Always a pleasure second time I have rented this house....Nicole is always attentive to our needs and house is always perfect.....Thank you for a second pleasurable trip.
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    About this property
    This home sits on 2.2 private and gated acres surrounded by nature. Viking kitchen, double sinks, double dishwashers and wine cooler. Six well appointed bedrooms, 3 en-suite. Three fireplaces. Formal living room, den, outdoor den, outdoor living room, formal dining room, covered porch with dining...
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    Sag Harbor, Hamptons 11937
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Wi-Fi
    • Washer
    Suitability
    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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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    • Grill
    • 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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    Location Information
    Westhampton Beach, Hamptons 11978
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    LUXURY HAMPTON ESTATE 4  PRIVATE RENTALS W/TENNIS,1 / 61
    (7)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Patio
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • DVD Player
    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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    Location Information
    Westhampton, Hamptons 11977
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
    Sag Harbor Village Fringe, Great Location1 / 18
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 29, 2018
    Was very happy with house , I had a wedding in Sag harbor and close proximity to town was perfect. Lovely property just wish it was warm enough to use the pool....
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    About this property
    This property has just gone through a hi-end renovation. It has a beautiful updated Viking kitchen, amazing yard with a 50 ft gunite pool with shallow end 'tanning bed', great for kids and adults alike! There are four bedrooms, 3 full baths in the main house, plus an additional full bath in the...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    7 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
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    • 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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    Location Information
    Westhampton Beach, Hamptons 11978
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 20
    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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    Location Information
    Remsenburg, Hamptons 11960
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    Chic Bridehampton Pristine Designer Home + Free Pool Heating!1 / 20
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2019
    What an amazing place! We loved every minute - the house is spacious, comfortable, stylish and is equipped with everything you could possibly need plus more.We stayed for 8...
    Reviewed June 6, 2019
    My stay here was amazing. The location was great. The house is beautiful. Lisa, the owner, had great communication with me from the time I booked until check out and even...
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    About this property
    Bridgehampton White 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** OVERVIEW OF HOME: 3 bedrooms 3 bathrooms Finished Basement with...
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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    East Hampton Dream House 'Serendipity' - Great Buy1 / 7
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 3, 2018
    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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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    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
    • Secure Parking
    • Children's Pool
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    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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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    Very Private and Tranquil  House in wooded estate.1 / 20
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Hamptons Retreat  *Pool & Spa*1 / 27
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    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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    East Quogue, Hamptons 11942
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Beautiful East Hampton Home / Heated Pool / Luxury Sheets and Towels1 / 23
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 11, 2017
    Gorgeous decor throughout this clean and comfortable home in a quiet, peaceful setting. Grounds and pool are beautiful and so relaxing. The gracious owner is super attentive...
    Reviewed August 16, 2015
    July 2015 we stayed one week in this beautiful East Hampton house. The house is very complete, clean and comfortable. It is everything but a standard rental house. You are...
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    About this property
    Beautiful contemporary style 4 Bedroom 3.5 Bath home with large bedrooms and brand new modern Kohler baths. Large windows, modern/Art Deco furnishings, new kitchen, new washer and 2 dryers. Great quality towels, Italian sheets (by Frette) provided. Great beach towels (Jonathan Adler). Large 20x40...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    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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    Pet friendly
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    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
    Beautiful East Hampton Home w/ Hot Tub & Pool!1 / 29
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 10, 2019
    Our contact for this rental was very nice and responded immediately to any concerns and questions I had. I was able to get an earlier arrival time which really was convenient...
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    About this property
    Explore East Hampton from this spacious 4-bedroom, 4-bathroom vacation rental home. The property features 2,500 square feet of living space, sleeping accommodations for 8, private hot tub, outdoor shower, and a new seasonal inground swimming pool! Situated less than a mile from the beach, you can...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Gorgeous Vintage Farmhouse, Pool/Central Air, Town 4 min Walk, Beach 8 min Drive1 / 34
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 1, 2018
    Peaceful, relaxing, comfortable farmhouse that we fell in love with. Coming from New York City we were ready to lay by the pool, read a good book, and have a glass of wine on...
    Reviewed August 1, 2018
    Lovely home, well-maintained, beautifully and comfortably furnished. We loved hanging out on the porch and enjoyed the outside fireplace. The beach is an easy, close drive...
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    About this property
    Our historic landmark Farmhouse is in the lovely, quiet village of East Quogue (Town of Southampton) in the part of the Hamptons that avoids the one-lane traffic to points further east. It has a beautiful wraparound porch and garden, a 16' x 32' heated pool, is completely updated with modern...
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    East Quogue, Hamptons 11942
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Vacation complete renovated great for entertainment1 / 26
    (2)Terrible
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    No smoking price is per couple All updated and renovated beautiful backyard large bedroom sizes huge kitchen 5 LARGE BEDROOMS entertainment room, outdoor shower, outdoor kitchen. All brand new appliances. Bar in kitchen. Wine cooler and 2 separate zinks. Additionally there is an extra room for...
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    Westhampton Beach, Hamptons 11978
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your best Hamptons summer in this fabulous house centrally located in Wainscott. There is room for the whole family in this 6 bedroom house, with heated pool, hot tub, and billiard room. Over 3000 square feet of covered and uncovered porches, patios, and decks. Kitchen is outfitted with...
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    Wainscott, Hamptons 11975
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    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)
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    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
    Spectacular Water Views & Sunsets in East Hampton1 / 13
    (3)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sited perfectly on the eastern shore of beautiful Three Mile Harbor in East Hampton, 'Island View' offers sweeping views of the water and a picturesque island in the foreground. Its ideal vantage point offers spectacular sunsets over the harbor. This bright, light, 4 bedroom, 4 1/2 bath vacation...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A truly peaceful getaway a few minutes from Southampton Village and beaches. This lovely home is recently updated and tastefully decorated with an inviting open floor plan kitchen, living and dining room that includes a working fireplace as its centerpiece. The house sits on a quiet street with...
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    Location Information
    Hampton Bays, Southampton 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy acre beautiful parcel sits this updated light filled home in a Development with wide street for walking. With 4 Master Ensuite bedrooms, spacious with 2 masters with king beds and private baths, one with queen bed and private baths and the other with two twin beds and private bath...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Post Modern Quaint Home Near  Beach1 / 71
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 18, 2018
    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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    Hampton Bays, Southampton 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    About this property
    Monthly Rental Only! 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 & BBQ...
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    Water Mill, Southampton 11976
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Hamptons private beach front home + pool1 / 17
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Ocean Views
    • Washer
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    • Waterfront
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    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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    Hampton Bays, Southampton 11946
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    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)
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    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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    East Hampton, Hamptons 11937
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    7 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    • Sauna
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    Pet friendly
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    About this property
    9 unique acres in the number 1 zip code in American, and backed up again 40 acres of Green belt. My home is one of 3 structures on the property, the Main house, Carriage, and the Cottage. The Main house is 6 bedrooms and the Carriage house is a Master suite with 900sq feet boasting a beautiful...
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    Sagaponack, Hamptons 11962
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 20
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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
    6BR Montauk House w/Pool & Ocean Views!1 / 25
    (1)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Ocean Views
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 15, 2019
    The most impressive aspect of this house is its beyond beautiful private backyard. The pictures do not do it justice. There is plenty of outdoor seating for a large family. We...
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    About this property
    Spend your New York retreat in style by staying at this exquisite 6-bedroom, 4-bath vacation rental home. With room for 13 guests, outstanding at-home amenities including an outdoor swimming pool, fire, and a prime location just a short walk from the beach, this home has everything you need for the...
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    Montauk, Hamptons 11954
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 13
    Bridgehampton Village Beauty1 / 26
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    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
    Lavish Southampton House w/Private Beach & Pool!1 / 32
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 15, 2017
    My husband and I stayed here over the fall for the long weekend. The house and décor were truly beautify, exactly what you’d think of for Hamptons style. It had big bay windows...
    Reviewed May 22, 2017
    Came here for a couples getaway with my wife and some friends. Had a great time and ended up inviting some friends from CT to join us when we realized the house sleeps many more...
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    About this property
    Experience the exquisite relaxation of upper Long Island, New York by staying at this luxurious 4-bedroom, 4-bathroom Southampton vacation rental home, which sleeps 8! With incredible upscale amenities, an alluring private pool, wraparound deck with bay views, exclusive access to a pristine natural...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 room/dining room/kitchen area. This is...
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    Location Information
    Amagansett, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    8 BR Luxury Oceanfront House Pool+Jacuzzi On Ocean. Call For Holiday Deals!1 / 40
    (2)Excellent
    8 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed May 20, 2015
    I rented this house for a reunion weekend and had a blast. To start, the house was beautiful, spacious and nicely accommodated my group of 14. Everyone had a bed and was able...
    Reviewed May 14, 2015
    We stayed here for the extended weekend (Thurs-Mon) and it was everything we could have ever imagined. The weekend went swimmingly and the beach house was beautiful. Very clean...
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    About this property
    This magnificent oceanfront beach house on Dune Road is surrounded by panoramic ocean views, featuring eight bedrooms (both deluxe master bedrooms and 2 more spacious bedrooms are panoramic to the ocean, and all 8 bedrooms have balcony access), seven and a half luxury baths, unique family room with...
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    Location Information
    Westhampton Beach, Hamptons 11978
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 18
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house has it all! 3 bedrooms with plenty of space for addition guests to sleep in the den. 2 bathrooms. Big living room, dining room, eat in kitchen. The den boasts a large screen TV with surround sound. Patio with furniture and gas grill. Heated pool! Dish washer in kitchen. Washing machine,...
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    Location Information
    Bellport, Long Island 11951
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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