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Holiday Rentals with Pools in Long Island

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    Travellers to Long Island are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    158 Matching Rentals in Long IslandView all 446 rentals
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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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    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Hip & Stylish East Hampton Getaway1 / 24
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    5 bedroom Private Family Get Away1 / 45
    (2)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Children's Pool
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 December 2017
    Our family of 9 adults & 4 children spent two wonderful nights at this house. We had more than enough room & felt comfortable. There was even a room for 93 year old...
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    About this property
    Private, spacious 5 bedroom, 3 bath home w/yard for relaxing, entertaining & sports. In deck heated pool w/safety fence. Huge kitchen, premium cable, wi-fi, fireplace. Neighborhood ideal for families - long walks, bike rides, wildlife watching. Large great room with skylights includes open kitchen,...
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    Westhampton Beach, Long Island 11978
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    • Grill
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Cable/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: Please contact us for 2+ week early Bird specials. Peace and quiet awaits in this modern house on the village fringe, featuring a first floor master with walk in closet, wonderfull spa-style master bath, flatscreen TV and direct access to the pool and outdoor shower. The kitchen, the...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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 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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    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 4 September 2017
    Highly recommend this house. Clean, large enough for to fit our 2 families very comfortably. Owner was very responsive.
    Reviewed 3 September 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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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated, 5 bedroom 3 1/2 bath home with separate TV room. 2 car garage with plenty of extra space for parking in the driveway. Pool, hot tub and large backyard with indoor and outdoor fireplaces. Close to both the bay and the ocean. Three Mile Harbor is in walking distance. Very quiet,...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Hamptons Beach, Quogue New Availability for the Holidays1 / 17
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Patio
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Internet Access
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 September 2017
    We used Vincent's house for a long weekend Highschool reunion. The house was perfectly set up for us when we arrived, clean and welcoming. Towels were in each room and a bottle...
    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 holiday goose and stuffing balanced on her knee? Will your mother in-law fill your entire kitchen.... with herself... only to find out the roast she bought doesn't fit in your oven? Well it is time to escape to beautiful Quogue...
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    Quogue, Hamptons 11959
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    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 25 June 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 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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    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    'Pennies From Heaven'1 / 25
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/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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    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
    • Cable/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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    East Hampton, Hamptons 11937
    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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    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Wi-Fi
    • Cable/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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    Southampton, Hamptons 11968
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/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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    Bellport, Long Island 11951
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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 30 August 2017
    This location was just perfect for our family. There was so much to do and enjoy. We were looking for a spot that satisfied my athletic sons, my mellow daughters and our three...
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    About this property
    8 ACRES: Rare privacy in East Hampton, NY nestled on 8 acres, Northwest pine tree forest, PRIVATE TENNIS, miles of walking trails. Truly a getaway to nature yet 3 minutes to Sag Harbor and East Hampton, shopping, and restaurants. 1 mile to glorious sunsets bay beach... ideal for little children....
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    East Hampton, Hamptons 11937
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    Bridgehampton Designer Decorated Pristine Modern Home w/ Heated Salt Water Pool1 / 20
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Parking
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 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.
    Reviewed 5 August 2017
    We had a wonderful two weeks there with our (very young) kids. The owners are kind and helpful not to mention very communicative. We were so happy with it all, can't wait to...
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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 TV...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Wi-Fi
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly build home, no expense spared. Beautiful pool and outdoor dining and cooking/BBQ area. The prefect home for entertaining and relaxing. Fully equipped kitchen for cooking and dining, plenty of space for entertaining. Master bedroom is fit for royalty, 4 more beautiful bedrooms in main house....
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    Southampton, Hamptons 11968
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Ground floor sunlit apt. in great area!1 / 16
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Shared Garden
    • Central Heating
    • Parking
    • Washer
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2017
    Everything was super simple and easy. The owner Rob very nice and helpful. He took the time to explain everything and let us know about all the activities and locations near...
    Reviewed 29 March 2017
    Excellent neiborhood, excellent communication with the owner.!! Highly recommended as **** four starts plus
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    About this property
    Ground floor of hi ranch includes large LR/kitchen combo and separate BR. Fully furnished with queen sized bed with Simmons beauty rest 12' mattress! There is also a pullout couch, new flooring, etc. You will have key to house & separate apt. to come & go as you please. In season there is a...
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    Huntington, Long Island 11743
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
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    • Patio
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stylishly decorated home is perfectly located near the town of Sag Harbor…close to vineyards, beaches, restaurants, shopping and theaters. You will have all the privacy you want. Outside you have a beautiful pool, huge deck with BBQ grille, fire-pit and outdoor shower. Inside you have a...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • DVD Player
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    • 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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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    • DVD Player
    • 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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    Southampton, Hamptons 11946
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    LUXURY HAMPTON ESTATE 4  PRIVATE RENTALS W/TENNIS,1 / 44
    (7)Excellent
    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Patio
    • Private Outdoor Pool (Unheated)
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    • Hot Tub
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 October 2015
    Mark was really wonderful to work with and very friendly. He made sure to meet us at the house and personally give us a tour/show us the many amenities the house had available...
    Reviewed 19 August 2015
    Mark was a very fun and gracious host, meeting us upon arrival to provide a full tour of all the amenities (the house has many!) from his vintage toy collection to where the...
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    About this property
    ALL THE LUXURY IN AND OUT, WITH AMENTIIES UNHEARD OF IN ANY OTHER HAMPTON ESTATE RENTAL: This is strictly a private rental. preferably for families or responsible groups. We have 6 bedrooms and a separate 2 l bedroom pool house. Note the pool house is 'campy' and fun no where near the...
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    Westhampton, Hamptons 11977
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    East Hampton Luxury Home  PERFECT FOR FAMILIES1 / 34
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Grill
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful summer home sits on an acre property only 3 years old and newly painted and furnished by Perter Andrews. It has a salt water heated pool, new cedar children's jungle gym with swing set, elevated ceder deck, dining room that seats 10, Eat-in kitchen that seats 8, fireplace with...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Hampton Bay Home Getaway -- 2500sqft, 3br (sleeps 12) - 3 full bths & 1 half bth (HUGE Master Suite), sitting rm w/fp, living rm, dining rm, eat in kitchen, billiard room & game room -- Large Backyard w LARGE in-ground heated pool, wood burning fire pit, barbecue grill, sand volleyball...
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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Cable/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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    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 3 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
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    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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    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    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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    Very Private and Tranquil  House in wooded estate.1 / 20
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 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 15 August 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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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the beautiful and immaculate five bedroom, four bathroom house in Sagaponack, New York.  Centrally located...five minute drive from Sag Harbor, five minute drive from the ocean and our amazing beaches.  Pine hardwood floors, contemporary furnishings with all the latest amenities.  Full...
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    Sagaponack, Hamptons 11962
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Vacation complete renovated great for entertainment1 / 15
    (2)Terrible
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    No smoking price is per couple All updated and renovated beautiful backyard large bedroom sizes huge kitchen 5 LARGE BEDROOMS entertainment room, outdoor shower, outdoor kitchen. All brand new appliances. Bar in kitchen. Wine cooler and 2 separate zinks. Additionally there is an extra room for...
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    Westhampton Beach, Long Island 11978
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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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
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 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 6 August 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 8 Quick View
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    • Air Conditioning
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    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* OVERVIEW OF HOME: 3 bedrooms 3 bathrooms Finished Basement with TV...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to your private Hamptons escape! Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this immaculate Southampton vacation rental house is sure to provide the perfect spot for families or a close group of friends traveling together. Boasting a beautiful...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 7
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    • Private Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3500 sq ft Hampton's styled home has a large light filled living room with fireplace and sliding glass doors to the expansive deck with heated pool. The open floor plan makes this home perfect for entertaining. This home is situated on .75 of an acre of property that backs up to a private...
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    Location Information
    Water Mill, Hamptons 11976
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Immaculate 4BR Southampton House w/Private Pool!1 / 32
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    My husband and I stayed here over the fall for the long weekend. The house and décor were truly beautify, exactly what you’d think of for Hamptons style. It had big bay windows...
    Reviewed 22 May 2017
    Came here for a couples getaway with my wife and some friends. Had a great time and ended up inviting some friends from CT to join us when we realized the house sleeps many more...
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    About this property
    Experience the exquisite relaxation of upper Long Island, New York by staying at this luxurious 4-bedroom, 4-bathroom Southampton vacation rental home, which sleeps 8! With incredible upscale amenities, an alluring private pool, wraparound deck with bay views, exclusive access to a pristine natural...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enchanted Garden setting is the perfect way to describe this Cottage that is walking distance to one of the most Beautiful Private Bay Beaches in the Hamptons! This immaculate home has three Bedrooms & two renovated custom designed bathrooms. You will be surrounded by Hydrangeas and Roses when you...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 9 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated perfectly on Davids Lane in East Hampton Village and South of the Highway, this exquisitely reconstructed1933 Shingled Classic has 7 bedrooms and 7 and 1 half bathrooms ,set on very private acre with close proximity to town shopping, Jitney stop, Duck Pond, Maidstone Club, and Village...
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    East Hampton, Hamptons 11937
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 12
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    5 Bedrooms, 8 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Waterfront
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    • Ocean Views
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ​This magnificent oceanfront estate in Montauk on Long Island's eastern tip is truly one-of-a -kind. This 5 bedroom, 7 bath home has been cleverly designed to maximize the spectacular ocean views from every possible vantage point. The open floor plan includes a living room with cathedral...
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    Montauk, Hamptons 11954
    Holiday Rental House - 5 Bedrooms, 8 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Contemporary Chalet with pool, beautifully furnished, is now available for Montauk's most beautiful season of all … Indian Summer. Accepting reservations for Sept & Oct. 3 Bedrooms / 2 full baths + Outdoor shower Room. Huge wrap around cedar deck. AC in every room (never needed). Perfect central...
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    Montauk, Hamptons 11954
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Well appointed 7000 sq. ft. traditional Hamptons home situated on 1.40 acres bordering a 32 acre reserve. 6 bedrooms and 5.5 baths, huge eat in kitchen, formal living and dining rooms, bar and an oversized gunite salt water pool and spa. Center foyer opens to a dining room with butler's pantry,...
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    Water Mill, Hamptons 11976
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a great summer retreat? Restaurants, antiquing, wineries, biking, canoeing, tennis, golf and of course the beach are all yours to be had at this charming east end gem on laid back Shelter Island. This renovated Country Cape is nestled on a spacious and lush ¾ acre wooded lot....
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    Shelter Island, Hamptons 11964
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hamptons Retreat -Large Pool & Spa - SEP AVAILABLE1 / 23
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Centrally located and completely renovated! Lovely two story Victorian home - 3 bedrooms, 2 full baths with central air. The perfect place to rejuvenate and indulge. Unwind in the hot tub among hydrangeas and roses. Breakfast on the sun porch. Dine at one of many Zagat rated restaurants. Walk...
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    East Quogue, Hamptons 11942
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    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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    Hampton Bays, Hamptons 11946
    Holiday Rental House - 4 Bedrooms, 3 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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    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, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape from everything at a private beach with gorgeous sunsets or dive into the backyard pool for a refreshing swim. Bright, open floor plan features a new kitchen and ample decking with an outdoor shower. Featuring 3 bedrooms and 2.5 brand new bathrooms. Wood burning fireplace in main living...
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    Springs, Long Island 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Serene & Private East Hampton Summer Rental w/pool1 / 19
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
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    • 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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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Hot Tub
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 & jacuzzi. The home is clean, stylishly decorated, and steps away from a gorgeous North Sea bay beach. Visit Southampton or Sag Harbor town only 3 min...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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