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Long Island Holiday Vacation with Pools

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    Travellers to Long Island are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    173 Matching Rentals in Long IslandView all 468 rentals
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    Hip & Stylish East Hampton Getaway1 / 24
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    20% OFF !!! Village Fringe glassy Modern with Pool and Tennis1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    5 bedroom Private Family Get Away1 / 45
    (3)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Beech Tree Cottage1 / 16
    (4)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 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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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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. ONLY 1 SUMMER WEEK LEFT! 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 ocean...
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    Cherry Grove, Fire Island 11742
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Romantic Getaway in Southampton (private room/bathroom)1 / 14
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    Great location. Beautiful grounds. Gracious host. The home was easy to find, peaceful and located in an area of that made getting around central Long Island simple and...
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    About this property
    Newly renovated house with nice spacious rooms with comfortable new double beds. Double occupancy room /private bathroom/entrance, queen size bed newly renovated 4 bedroom-3 bathroom home in prime Southampton location. Close to bay, beach and town. Directly across the street from the fascinating...
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    Location Information
    Southampton, Hamptons 11968
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Montauk Royal Atlantic Beach Resort1 / 8
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 26, 2016
    We have been going to the Royal Atlantic every year except for one year.It has gone downhill for a few years now.We keep going back because of the location. We have a...
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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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    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
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    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (10)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 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.
    Reviewed October 15, 2016
    That's it! Unit was clean and comfortable. Beach was right there. Drive to town or spots of interest easily. Compact, well organized, nice little terrace overlooking the water...
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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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    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 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
    • 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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    Location Information
    Hampton Bays, Southampton 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    10 Minutes to Ocean Beaches. Poolside1 / 30
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 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 your summer relaxing by the heated pool or enjoying the close beautiful bay beaches of the North West Woods or just a quick car ride to a sandy ocean beach of the Hamptons. This charming air-conditioned home is sited on a privately landscaped half acre property. An open light filled great...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3BR/2BA- Private Heated Pool Steps to Moriches Bay1 / 21
    (2)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 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...
    Reviewed June 14, 2014
    We have rented the house for a long week. The contact with Christine was excellent. The info and the keys were all where they should be. The house is clean even for German...
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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, Long Island 11960
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful custom built 2 bedroom home offers authentic charm and elegance from the finishing to the furnishings. It is located in a waterfront community just steps to the Peconic Bay with access to launching your boat! Enjoy the view of the heated pool from a spacious deck overlooking a large...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    East Hampton Dream House 'Serendipity' - Great Buy1 / 7
    (2)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 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...
    Reviewed June 10, 2016
    My wife and I stayed in this lovely house in May 2016.A lovely quiet area approx. 1/4 mile off the main road so supremely quiet.It was very well furnished and equipped and...
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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
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    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
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    East Hampton Classic1 / 22
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    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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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Post Modern Quaint Home Near  Beach1 / 71
    (4)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 September 4, 2017
    Highly recommend this house. Clean, large enough for to fit our 2 families very comfortably. Owner was very responsive.
    Reviewed September 3, 2016
    It is a very big and clean house with a big pool. Our families are so enjoy the time of staying here, and the homeowner is very helpful before and during the stay.
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
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    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bridgehampton Blue House RATES INCLUDE THE FOLLOWING: Electric consumption, cable TV & wi-fi, propane consumption, telephone, trash removal, lawn & pool service and pool heater set to 85 degrees between Memorial Day and Labor Day* PLEASE NOTE THAT THIS HOME IS ON THE MARKET FOR SALE AND IT IS...
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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Garden
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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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    Location Information
    Springs, Long Island 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large swimming pool (43' x 22' free form) with changing colors LED lights and water fall, a 10 people outdoor spa jacuzzi tub. Complete and well equipped outdoor kitchen, walking distance to the bay and 5 minutes drive to town or the OCEAN. Big and clean house in the woods. The house indulge...
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    Location Information
    Hampton Bays, Southampton 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    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
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Grill
    • Secure Parking
    Suitability
    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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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    East Hampton Family Retreat with Cottage1 / 41
    (4)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
    Please note: WEEKLY / MONTHLY ONLY IN JULY, AUGUST, THUR LABOR DAY! 3 night minimum for New Year's Eve weekend, and all holiday weekends, Friday to Monday at $800 per night, main house only. (cottage is booked) Please note, hot tub and pool are closed for the winter season. Hot tub reopens...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Patio
    Suitability
    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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    Ocean Front Cottage Montauk for rent1 / 25
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Air Conditioning
    • Patio
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed August 29, 2017
    great location. close to everything. very family friendly. very clean, BBQ, outdoor shower as well as 1 full bath and 1 ½ bath. I would recommend this to my friends.
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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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    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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    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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A family place with wrap-around windows and skylights gives you the best of the Hamptons. Big beautify yard and gardens, magical garden-set pool, hot-tub and plenty of room for privacy, makes it a family dream. Backyard. 3 decks. Pool set amongst Maples and hibiscus. BBQ grill. Fresh herbs....
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect place to spend your vacattions! Located on the south shore of Long Island, 20 minutes from JFK Airport. Walk to the Long Island Railroad connecting to Air-train JFK. A 40 min train ride to NYC Penn Station! Enjoy all that summer has to offer! A 10 minutes drive to Long Beach, Jones...
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    Location Information
    Freeport, Long Island 11520
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    East Hampton Village - Walk to Shops, Bike Ocean!1 / 22
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Private Garden
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious Cape Cod design features four large, exquisitely furnished bedrooms, two full baths, stunning eat-in kitchen, sunny family/living room with fireplace, and separate dining room. A swimming pool, central air-conditioning, and high speed wireless internet access are just some of its...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
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    • Washer
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is Close to everything the Hamptons have to offer , your family will love this house and it's fantastic location!! In the area within a few block walk you will find many exciting restaurants, shops, movie theater, beach bars, and Jet Ski & boat rentals within 1 mile from the home. You...
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    Location Information
    Hampton Bays, Southampton 11946
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Patio
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is in the most desirable neighborhood in Southampton. Close to everything the Hamptons have to offer. You'll be near the beaches and the Village of Southampton - where you have many exciting restaurants, shops, movie theater, and night celebrities. (THIS HOUSE REQUIRES A 5 NIGHT MIN...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    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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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    Suitability
    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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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 3 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
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    • 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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    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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    • Washer
    • Wi-Fi
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    • Cable/satellite TV
    Suitability
    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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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
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    • Internet Access
    • 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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    Bellport, Long Island 11951
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    Suitability
    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Garden
    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    • Secure Parking
    Suitability
    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 Bridehampton Pristine Designer Home + Free Pool Heating!1 / 20
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Parking
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    • Private Outdoor Pool (Heated)
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    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 14, 2018
    This house is amazing! We celebrated a girls weekend with 6 people, and it was perfect for us — so spacious, clean, bright and beautiful. Every guest was blown away by the house...
    Reviewed October 9, 2017
    Some friends and I rented this property for a wedding weekend. This is a lovely home with a lot of space to lounge and relax and located nearby the Bridgehampton downtown area.
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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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
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    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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    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy 2 acre beautiful parcel adjacent to hundreds of acres of town reserve sits this updated light filled home with sweeping lawn, and reserves on 3 sides for complete privacy. Spacious with 4 bedrooms and 3.5 baths,Two masters with king beds and private baths, two additional bedrooms one...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Housekeeping Included
    • Washer
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the front is a beautiful woodland garden with rare woodland flowers and ferns, moss-covered boulders and miniature ponds. In the rear is a Japanese garden, complete with a moon bridge over a babbling brook, a waterfall you can swim behind, a pond house with a deck you can sunbathe or dive from,...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    East Hampton/Sag Harbor Village Fringe1 / 26
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • 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
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    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    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
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
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    • Waterfront
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    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Southampton, Hamptons 11946
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Cable/satellite TV
    • Hot Tub
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    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in all that East Hampton has to offer at this stunning 4-bedroom, 3-bathroom vacation rental house that comfortably sleeps 10. Situated on 2 acres of fenced land with a playground, lush grass, private hot tub and 50-foot pool with 10 chaise lounge chairs, you'll feel as though...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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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