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Long Island Holiday Vacation with Pools

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    $1,423 Average
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    Travellers to Long Island are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    244 Matching Rentals in Long IslandView all 725 rentals
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    Hip & Stylish East Hampton Getaway1 / 24
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Post Modern Quaint Home Near  Beach1 / 71
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 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...
    Reviewed 4 August 2016
    The condo was very comfortable. Greenport is a great town with lots of restaurants and shops.There are many vineyards right in the area and you couldn't get any easier access to...
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    About this property
    Overview: Waterfront Water's Edge suite, Suite C-204, accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. Quoted rental rates include all taxes, I do not charge resort fees...
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    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    East Hampton Dream House 'Serendipity' - Great Buy1 / 7
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • DVD Player
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    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 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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    3BR/2BA- Private Heated Pool Steps to Moriches Bay1 / 20
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Heated)
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    • Patio
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    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 June 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 14 June 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. <BR><BR>Located on a small quiet...
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    Remsenburg, Long Island 11960
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Thanksgiving for ALL the Family in beautiful Quogue.1 / 17
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Patio
    • Private Outdoor Pool (Heated)
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    • Internet Access
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 May 2016
    This house is really awesome. Everything was exactly as described. Owner respond quick to all your questions.
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    About this property
    Will your mom have to sit on the end of your futon with a plate of turkey and stuffing balanced on her knee? Will your mother in-law fill your entire kitchen.... with herself... only to find out the Turkey she bought doesn't fit in your oven? Well it is time to escape to beautiful Quogue and have...
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    Location Information
    Quogue, Hamptons 11959
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • DVD Player
    • Washer
    • Patio
    • Porch
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are a family of 4. My kids love that I made a tv/playroom next to my kitchen separated from our own TV in the open kitchen/living room space. This house is located in the Best area in the Hamptons. 5 minutes drive from Sag Harbor Main Street, 7 minutes drive to East Hampton Main Street, 15...
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    Wainscott, Hamptons 11975
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Elegant Designer Hamptons Retreat in Sag Harbor1 / 28
    (4)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
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    • 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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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 12
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    Village Fringe glassy Modern with Pool and Tennis1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2017
    My family was looking for a quiet house to relax in a beautiful setting, and we had just this house. This sunny, bright, clean and pleasant...most of all, luxurious house with...
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    About this property
    SPECIALS: July 21-31 (=2 weekends!) at only 10k plus cleaning and pool heat (=10.75k Total) Peace and quiet awaits in this modern house on the village fringe, featuring a first floor master with walk in closet, wonderfull spa-style master bath, flatscreen TV and direct access to the pool and...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Montauk - 6 BR / 4 Bath House w/ Pool & Beach Pass1 / 24
    (6)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Internet Access
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2016
    Came with a group of girlfriends to relax and enjoy Montauk at the end of the off-season - it was a great house for a bunch of adults to hang, and was well also well set up for...
    Reviewed 6 December 2014
    We rented this house for a week because our son was being married in Montauk. It was perfect for our needs. We were able to accommodate extended family members with enough...
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    About this property
    East Hampton Rental Registry #16185 *** Please see Summer 2017 (May - October) availability, minimum stay requirements and pricing information at the end of this listing before contacting *** Thinking of spending time in Montauk? Great idea! Enjoy all the East End has to offer from the comfort of...
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    Location Information
    Montauk, Hamptons 11954
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Secure Parking
    • Children's Pool
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Updated recently , professionally painted, this home has a cozy feel,open plan available indoors. First floor has for guests : 2 Queen size bedrooms, 2 full marble bathrooms, formal blue dining room,fully equipped and renovated marble kitchen,(stainless steel appliances, incl. dishwasher), also a...
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    Location Information
    Hampton Bays, Hamptons 11946
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    10 Minutes to Ocean Beaches. Poolside1 / 15
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Satellite TV
    • Hot Tub
    • Patio
    • Housekeeping Included
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 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 4 August 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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    Luxury Hamptons Quogue Village 4BR Modernist Retre1 / 30
    (3)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Satellite TV
    • Grill
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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 3 August 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 5BR+, 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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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Hot Tub
    • Washer
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning contemporary house is set on two private acres in the near Northwest Woods. Bright, white filled with sunlight, this four bedroom, two and a half bath multi-level home has soaring cathedral ceilings on the main level, large king master bedroom suite with private deck, TV, new bath...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Internet Access
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Ocean Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 90 minutes from Manhattan, but worlds away from NYC! In the Fire Island Pines, an idyllic gay community (but friendly to all) on the beach with no cars, just the deer roaming wild. The cabana is small but very self contained. BBQ on the deck overlooking the ocean. 5 minutes walk to "town"...
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    Location Information
    Fire Island Pines, Fire Island 11782
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Patio
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming House near ocean, walking distance to Amagansett village and farm stores. Located between East Hampton and Amagansett village less than 2 miles South to ocean beach or north to Three Mile Harbor. Consisting of 3 bedroom and bathrooms, living room, dining room family room that could act...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 8
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    Westhampton Beach Village  LONG ISLAND New York1 / 15
    (3)Terrible
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Grill
    • Porch
    • Patio
    • Shared Garden
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home secluded area. Just renovated. Near everything ocean and beaches. Big backyard. Sports play. Outdoor kitchen-Pool-outdoor shower-circular driveway-6 cars parking. Huge kitchen island and bar sink. 3 masters suites second floor. 3 others large sizes 1st floor. Finished basement too....
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    Location Information
    Westhampton Beach, Long Island 11978
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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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
    • Satellite TV
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    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Washer
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is modern, clean and comfortable. few blocks to social club and 75 main!! It is located in the heart of the Southampton! The house is located just a few blocks from the Village of Southampton and a few blocks from the most beautiful beaches in the world. It is in one of the most desirable...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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)
    • Satellite TV
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 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 12 June 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, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    • Air Conditioning
    • Parking
    • 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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    Location Information
    Bellport, Long Island 11951
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    • Children's Pool
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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, Long Island 11978
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Family fun luxury waterfront home with pool.1 / 15
    (4)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Waterfront
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2015
    As I walked into the house for the weekend that we spent there for my sister's bachelorette party, I was in awe of how gorgeous the property was. The house was absolutely...
    Reviewed 25 February 2015
    We saw the house before we rented so there were no surprises except the extra little items provided. Our family has rented often before and items like condiments, towels, bed...
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    About this property
    Large luxury air conditioned home located on Reynolds channel. Fish off the dock ,bring your boat and moor it in the yard or just enjoy the heated pool, short walk to town and beach. Take the train into NYC in less than an hour. Indoor and outdoor fireplace. 4 bedrooms and 3 bathrooms on the...
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    Location Information
    Long Beach, Long Island 11561
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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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
    • Satellite TV
    • Grill
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    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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    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    • Private Garden
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    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, Hamptons 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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    • DVD Player
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located a few blocks from Wollfer Vineyard and blocks away from the town of Sag Harbor. You will have all the privacy you want. Enjoy a beautiful built in pool. The home is clean, stylishly decorated, and close to gorgeous beaches. Work out room, everything! The location...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
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    • Hot Tub
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located in Southampton. The house is nestled in a park like setting with a private tree-lined yard. You will have all the privacy you want. Enjoy a beautiful built in pool with hot tub. The home is clean, stylishly decorated, and steps away from a gorgeous nature preserve. (...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    • Washer
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    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Be close to everything the Hamptons has to offer while getting away from it all in your little piece of paradise.! You'll be a mere 1 mile away from the ocean beaches of and in close proximity to the Hampton Village of Southampton - with its exciting selection of restaurants, shops, movie theater,...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
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    • Grill
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury in the woods by day, Romantic ny evening. 3000 sq.ft, 2014-16 Total Renovation + Architectural Additions (Interior, Exterior, Landscaping), Total refurnishing.Traditional Saltbox style made 'light-filled' with Contemporary additions, SoHo loft-style interior, 25' Cathedral ceilings, Custom...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    Ocean Front Cottage Montauk for rent1 / 14
    (3)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Internet Access
    • Patio
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    • Waterfront
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 September 2016
    My husband and I come to Montauk every September - the light is beautiful, beaches less crowded, and we love the combination of warm days and slightly chilly nights. This is a...
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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, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
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    • Hot Tub
    • Washer
    • Grill
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Southampton home. Very private with a large pool and a beautiful, large Jacuzzi. This home is perfectly located in Southampton. Sleeps 13. If you have been wanting to visit The Hampton's for the first time house is the perfect choice since its perfectly located in the heart of the...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    • Washer
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    • Private Outdoor Pool (Unheated)
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located in Southampton. It is a 4 Bedroom, sleeps 10. If you have been wanting to visit The Hampton's for the first time this house is the perfect choice since its perfectly located in the heart of the Hampton's, just a three minute drive to the village with all the...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    >>> ROMANTIC Beach Getaway! Seclusion, Waterfalls1 / 20
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
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    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With it's Caribbean flair, 3 waterfalls, 2 pools and 75' Koi pond, our Vacation home is possibly the most Romantic Hamptons Hideaway Vacation Cottage Home Rental ever. Located in the Estate Section of Shelter Island. Available weekly, monthly or for the entire season contact us early for your...
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    Shelter Island Heights, Shelter Island 11965
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cliffside Resort Greenport Luxurious Waterfront Condo- with Pool!1 / 8
    (33)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Terrace
    • Internet Access
    • Satellite TV
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2015
    My college friends & I have been coming here for @ 6 years...nowhere better....the condo is clean and nicely decorated......if you choose water view/front...well worth the...
    Reviewed 6 August 2014
    Enjoyed four night stay .condo unit &entire complex was clean and well maintained.Location was perfect for touring vineyards ,Shelter Island and Greenport attractions.Pool...
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    About this property
    As featured by New York Magazine, the Cliffside Resort entertains the perfect vacation! This 68 unit complex, located directly on the Long Island Sound with incredible sunset views, offers brand new 2 bedroom 2 bathroom luxurious accommodations. Cliffside Resort Waterfront Condominiums at...
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    Location Information
    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Satellite TV
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Hot Tub
    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, and 50-foot pool with 10 chaise lounge chairs, you’ll feel as though you’re staying at a...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    SECLUDED BEACH CONTEMPORARY ESTATE1 / 23
    (3)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2016
    Our family had a lovely time during our stay at this house, the amenities were great and we had a warm welcome when we got there. the pool, hot tub, and game room were all above...
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    About this property
    Only 600 feet from one of the most beautiful (private) Hampton's beach. Enjoy poolside living in this stunning contemporary home complete with lots of skylights and cathedral ceiling. Bike along the Peconic Bay or enjoy miles of sandy beach just steps away. This spacious home has a large heated...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    Very Private and Tranquil  House in wooded estate.1 / 20
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Satellite TV
    • Private Outdoor Pool (Unheated)
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    • Wi-Fi
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    In our travels, both short and long, at home and abroad, we always prefer to stay in small hotels or B & B. We try to avoid a large crowd and associated fuss, noise and...
    Reviewed 4 weeks ago
    Beautiful location with charming style and impeccable hospitality, delicious gourmet breakfasts, cozy and warm rooms, beautiful gardens and a pool. Lydia and Kazimir are the...
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Private Garden
    • Shared Outdoor Pool (Unheated)
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming, spacious, bright and quiet East Hampton home available year round, with a 2 night minimum stay now thru Memorial Day, and a minimum one week stay in the summer months. Bright & Sunny home has wood floors throughout, Cathedral ceiling in open living area with 3 skylights and 3 sets of...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located east of the canal on the beautiful Peconic Bay, over 100 feet of sandy beach, walk down the shore to for food, drinks and entertainment! Beautiful, crystal clear water, 5000 sq ft custom Waterfront “GREEN” House, 5 bedrooms, 5 baths , CAC, hardwood floors, in-ground heated pool, Outdoor...
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    Location Information
    Southampton, Hamptons 11946
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Secure Parking
    • Satellite TV
    • Private Garden
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    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the best season of the year in this lovely house in the heart of Bellport Village NY, an hour and half away from New York comfortably fit 2 adults and 2 child ( or 3 to 4 adults). The swimming pool makes it even more pleasant, like an oasis. This is a small house (800 sq/ft) with 2 bedroom...
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    Location Information
    Bellport, Long Island 11713
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Private Outdoor Pool (Heated)
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    • Wi-Fi
    • Waterfront
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning, spacious three bedroom home, with water views from every room, and a heated gunite pool, will be your dream-come-true vacation rental. You will be minutes away from several gorgeous beaches as well as 1 mile from the lively and historic village of Sag Harbor. Decorated to a high...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Satellite TV
    • Patio
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very nice 1 bedroom suite with big king size bed (kitchen is not available), very nice modern bathroom, very big modern living room with office desk and apple desktop computer. Our vacation rental is close to McArthur airport, city center, beach, nightlife, parks, public transport, Sunken...
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    Location Information
    Commack, Long Island 11725
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Satellite TV
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    • Internet Access
    • DVD Player
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    AVAILABLE Summer and Beyond. Wonderful, delightful, story book style cottage with white picket fence for your vacation pleasure ! This adorable 4 bedroom home is fully renovated, charming shabby chic decor. There is a heated pool and large driveway. BRAND NEW OUTDOOR SHOWER for sun-watering your...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Majestic Southampton Waterfront Estate1 / 55
    (7)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is extravagant living at its best. Picture yourself enjoying expansive water views and majestic sunsets. The park like setting lends itself to an idyllic outdoor paradise. This home has 7 huge bedrooms and 5 palatial bathrooms. The house boasts a wide-open floor plan with soaring cathedral...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 18
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    Immaculate & Spacious 4BR Southampton House w/Wifi, Firepit, Dazzling Private Pool & Spectacular Bay Views from Wraparound Deck - Only 200 Feet From Private Beach Access!1 / 32
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    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 4 weeks ago
    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 Southampton vacation rental home! With incredible upscale amenities, an alluring private pool, exclusive access to a pristine natural sand beach and close proximity to all the world-class attractions for...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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