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Holiday Rentals with Pools in Long Island

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    RM 3,929 Average
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    Travellers to Long Island are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    177 Matching Rentals in Long IslandView all 485 rentals
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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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    Beachy Keen - East Hampton NY1 / 15
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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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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    Hamptons Retreat  *Pool & Spa*1 / 28
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Centrally located and completely renovated! Lovely two story Victorian home - 3 bedrooms, 2 full baths with central air. The perfect place to rejuvenate and indulge. Unwind in the hot tub among hydrangeas and roses. Breakfast on the sun porch. Dine at one of many Zagat rated restaurants. Walk...
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    11942, East Quogue, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Hip & Stylish East Hampton Getaway1 / 24
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Grill
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2017
    My husband and I loved staying here with our two teenage sons. We visited from the UK and spent 4 nights in Manhattan before driving over to the Hamptons. We loved the buzz and...
    Reviewed 6 September 2016
    We loved the house and had a great stay in the Hamptons.The house is in a very quiet and beautiful environment, surrounded by trees, only a 10 minute drive max to East Hampton...
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    About this property
    Minimum two-week stay. This well-designed contemporary beach house with three bedrooms and two baths sits on an acre of blissful privacy. This vacation rental is located in East Hampton NW woods, 4 miles from East Hampton Village and 1.5 miles from Sammy's Beach. Close enough to it all, yet...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3BR/2BA- Private Heated Pool Steps to Moriches Bay1 / 21
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Grill
    • Patio
    • Washer
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2018
    Christine's house was perfect for our family stay in the Hamptons after a busy week with a family wedding in Brooklyn/New York. The children really enjoyed the pool and the...
    Reviewed 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...
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    About this property
    Easy summer living at this bright contemporary ranch located steps from Moriches bay in Westhampton/Remsenburg. Open kitchen- dining area, living room with fireplace, 3 bedrooms, 2 baths, central air conditioning, and a private yard with a heated swimming pool. Located on a small quiet block,...
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    11960, Remsenburg, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 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
    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 June 2017
    We just found out about this and it's a wonderful property. The town of Quogue houses some of the most successful people inNew York and is astronomically expensive.The Quogue...
    Reviewed 4 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 6BR, 4WC recently renovated in rustic modern style. Light and airy with skylights and large windows and doors. Huge chef's kitchen boasts 6 burner range and double sinks. Expansive 40 ft pool, 8 person hot tub, 1.3 acres on quiet wooded cul de sac, and Quogue Village beach...
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    11959, Quogue, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bridgehampton Blue House RATES INCLUDE THE FOLLOWING: Electric consumption, cable TV & wi-fi, propane consumption, telephone, trash removal, lawn & pool service and pool heater set to 85 degrees between Memorial Day and Labor Day* PLEASE NOTE THAT THIS HOME IS ON THE MARKET FOR SALE AND IT IS...
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    11932, Bridgehampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Gorgeous Vintage Farmhouse, Pool/Central Air, Town 4 min Walk, Beach 8 min Drive1 / 34
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2018
    Peaceful, relaxing, comfortable farmhouse that we fell in love with. Coming from New York City we were ready to lay by the pool, read a good book, and have a glass of wine on...
    Reviewed 2 August 2018
    Lovely home, well-maintained, beautifully and comfortably furnished. We loved hanging out on the porch and enjoyed the outside fireplace. The beach is an easy, close drive...
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    About this property
    Our historic landmark Farmhouse is in the lovely, quiet village of East Quogue (Town of Southampton) in the part of the Hamptons that avoids the one-lane traffic to points further east. It has a beautiful wraparound porch and garden, a 16' x 32' heated pool, is completely updated with modern...
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    11942, East Quogue, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 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)
    • Cable/satellite TV
    • Washer
    • 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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    11977, Westhampton, Hamptons
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    5 bedroom Private Family Get Away1 / 45
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Children's Pool
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2018
    The kids loved the pool! beaches are only a few miles away. We needed a few items and were happy to know that their were a shopping mall right around the corner!
    Reviewed 6 March 2018
    Carrie was a wonderful host and left my crew some champagne and cookies for the weekend! We used the house for a bachelorette party in the Hamptons in August and It was perfect...
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    About this property
    Private, spacious 5 bedroom, 3 bath home w/yard for relaxing, entertaining & sports. In deck heated pool w/safety fence. Huge kitchen, premium cable, wi-fi, fireplace. Neighborhood ideal for families - long walks, bike rides, wildlife watching. Large great room with skylights includes open kitchen,...
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    11978, Westhampton Beach, Hamptons
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    East Hampton Family Retreat with Cottage1 / 41
    (5)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 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
    2 night minimum weekends, 3 night minimum all holiday weekends. Hot tub and pool are closed for the winter season.. Hot tub closes Dec. 1st., 2018 Pool closes Oct. 1st. 2018 Please note! The base rates listed are off season ONLY, higher Memorial Day to Labor Day. Beautiful wooded property and...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Serene & Private East Hampton Summer Rental w/pool1 / 19
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    11937, East Hampton, Hamptons
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Quiet and Private in Heart of East Hampton Village1 / 13
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2015
    It was a delightful experience to stay at “The Vacationer” during my recent trip to East Hampton. The house is located in a very quiet neighborhood and is walking distance from...
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    About this property
    'The Vacationer' is a lovely, bright, white, 3 bedroom, 2 bath vacation home with a beautiful heated swimming pool. This extremely charming and appealing property features a pristine natural cedar Swedish sauna, central air conditioning, two flat screen TVs, high speed WiFi, and a new stainless...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful East Hampton Home / Heated Pool / Luxury Sheets and Towels1 / 23
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2017
    Gorgeous decor throughout this clean and comfortable home in a quiet, peaceful setting. Grounds and pool are beautiful and so relaxing. The gracious owner is super attentive...
    Reviewed 16 August 2015
    July 2015 we stayed one week in this beautiful East Hampton house. The house is very complete, clean and comfortable. It is everything but a standard rental house. You are...
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    About this property
    Beautiful contemporary style 4 Bedroom 3.5 Bath home with large bedrooms and brand new modern Kohler baths. Large windows, modern/Art Deco furnishings, new kitchen, new washer and 2 dryers. Great quality towels, Italian sheets (by Frette) provided. Great beach towels (Jonathan Adler). Large 20x40...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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 17 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. NOW TAKING RENTALS FOR 2019 Come join us in our fabulous get-a-way from the hustle and bustle of everyday life. This incredible 'gay' oceanfront property is nestled in Cherry Grove, Long Island which hosts beautiful white sandy beaches. Sleep to the...
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    11742, Cherry Grove, Fire Island
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Chic Bridehampton Pristine Designer Home + Free Pool Heating!1 / 20
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Parking
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We had a wonderful time at "the white house." It was light, bright, lovely, cheerful, clean and a perfect layout for the five of us - we were able to sleep in and enjoy...
    Reviewed 14 March 2018
    This house is amazing! We celebrated a girls weekend with 6 people, and it was perfect for us — so spacious, clean, bright and beautiful. Every guest was blown away by the house...
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    About this property
    Bridgehampton White House RATES INCLUDE THE FOLLOWING: Electric consumption, cable TV & wi-fi, propane consumption, telephone, trash removal, lawn & pool service and pool heater set to 85 degrees between Memorial Day and Labor Day** OVERVIEW OF HOME: 3 bedrooms 3 bathrooms Finished Basement with...
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    11932, Bridgehampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sag Harbor designer home, Chef's kitchen & one block from the water1 / 14
    (2)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2017
    We loved everything about this place. From the outdoor fire pit to my elderly parents having the time of their lives. Everything was impeccable. We look forward to returning...
    Reviewed 23 March 2017
    Our family enjoyed a great week in Sag Harbor and wonderful accommodations. The house is as advertised, nicely and warmly decorated with beautiful pool and outdoor grounds. The...
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    About this property
    For a truly authentic experience of Sag Harbor, stay at this delightful 5-bedroom, 2-bathroom designer's home with oversized heated pool and ideally situated just 2 blocks from Long Beach . With 2,800-square feet of living space and enough sleeping accommodations for up to 10 guests, this residence...
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    11963, Sag Harbor, Hamptons
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    11963, Sag Harbor, Hamptons
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 12
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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 13 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
    11946, Hampton Bays, Southampton
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    July - August 2017. Open floor plan, modernist house in the Village of Springs1 / 5
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 October 2017
    Beautiful open plan modernist home, close to both East Hampton and Amagansett towns but away from the hub-bub in country-like Springs. The house has a great pool and an amazing...
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    About this property
    Superbly designed by its owners, this dwelling boasts the elegance and sobriety of a minimalist painting. Yet, it remains very warm and inviting. The house sits on a wooded acre, across the road from a 140 acre reserve. The 2,500 sq. ft. space offers 2 bedrooms, 2 bathrooms, living room with wood...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
    • Cable/satellite TV
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 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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    11937, East Hampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    7 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Sauna
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    9 unique acres in the number 1 zip code in American, and backed up again 40 acres of Green belt. My home is one of 3 structures on the property, the Main house, Carriage, and the Cottage. The Main house is 6 bedrooms and the Carriage house is a Master suite with 900sq feet boasting a beautiful...
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    Location Information
    11962, Sagaponack, Hamptons
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 20
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    Post Modern Quaint Home Near  Beach1 / 71
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • DVD Player
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 days ago
    This house exactly served our needs for a family getaway for ourselves, our two adult daughters, their husbands, and two grandkids -- a newborn and a 2-year-old. There was...
    Reviewed 4 September 2017
    Highly recommend this house. Clean, large enough for to fit our 2 families very comfortably. Owner was very responsive.
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    About this property
    Immaculate four bedrooms, three full baths sleeps 8-10. Full gym, pool and jacuzzi nestled away in prestigious Red Cedar Ridge. Large deck with BBQ. Fully equipped kitchen. Wi-fi internet and premium channels cable tv. Pool table, basketball and children play ground for entertainment. Five min...
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    Location Information
    11946, Hampton Bays, Southampton
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Westhampton Waterfront 6 Bedroom Secluded 3 Acre E1 / 13
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • DVD Player
    • Internet Access
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Perfect Getaway Westhampton Waterfront Secluded Estate Drive along this Hamptons vacation rental properties private stonewalled 800 ft driveway and into what Hampton style living is all about. This home is located on three acres of beautiful waterfront property in Westhampton. With...
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    Location Information
    11977, Westhampton, Hamptons
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    • Patio
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming, private, 2 story cottage with outdoor balconies. 'Treehouse' feel with great wooded views. Queen bed, one loft bed, full bath, hardwood floors on second floor. Sitting area, twin bed on first floor with washer/ dryer. Covered balcony with gas fire ring, warm and cozy! Amazon / Netflix...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    East Hampton/ Sag Harbor, 8 Acres, Pool, Tennis Ct, Hot tub, Sauna1 / 16
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Secure Parking
    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 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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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ocean Front Cottage Montauk for rent1 / 25
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
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    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2018
    We were there to attend the US Open final day. It’s a reallly picturesque spot. The cottage has all you would need for a short stay getaway for 4. Linger stays might be a little...
    Reviewed 31 August 2017
    This was a small cottage with a spacious feeling. The ceilings were high and it was the perfect size for 4 people. We were able to cook breakfast everyday and it had most of the...
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    About this property
    It is a 1000 sq foot cottage which is private, surrounded by hedges with the master suite, kitchen, main room and decks all over looking the ocean. Very warm and cozy, with wood beam ceilings, modern kitchen with all new appliances including dish washer. This cottage has been in our family for...
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    Location Information
    11954, Montauk, Hamptons
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Private Outdoor Pool (Heated)
    • Private Garden
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enchanted Garden setting is the perfect way to describe this Cottage that is walking distance to one of the most Beautiful Private Bay Beaches in the Hamptons! This immaculate home has three Bedrooms & two renovated custom designed bathrooms. You will be surrounded by Hydrangeas and Roses when you...
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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    East Hampton/Sag Harbor Village Fringe1 / 26
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Grill
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 January 2018
    Always a pleasure second time I have rented this house....Nicole is always attentive to our needs and house is always perfect.....Thank you for a second pleasurable trip.
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    About this property
    This home sits on 2.2 private and gated acres surrounded by nature. Viking kitchen, double sinks, double dishwashers and wine cooler. Six well appointed bedrooms, 3 en-suite. Three fireplaces. Formal living room, den, outdoor den, outdoor living room, formal dining room, covered porch with dining...
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    Location Information
    11937, Sag Harbor, Hamptons
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    Sag Harbor Village Fringe, Great Location1 / 18
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Cable/satellite TV
    • Patio
    • DVD Player
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 2018
    Was very happy with house , I had a wedding in Sag harbor and close proximity to town was perfect. Lovely property just wish it was warm enough to use the pool....
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    About this property
    This property has just gone through a hi-end renovation. It has a beautiful updated Viking kitchen, amazing yard with a 50 ft gunite pool with shallow end 'tanning bed', great for kids and adults alike! There are four bedrooms, 3 full baths in the main house, plus an additional full bath in the...
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    Location Information
    11963, Sag Harbor, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Beech Tree Cottage1 / 16
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Shared Garden
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    • Outdoor Dining Area
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    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2018
    With a full kitchen and living room, outdoor terrace and perfect so-close-you-can-walk-to-town setting, you will be so happy you snagged this spot! I’m picky, and I know what’s...
    Reviewed 7 August 2016
    Spent two nights at Beech Tree with my husband and grown son. Cottage is located within walking distance of town, in a nice residential neighborhood. Kitchen is well stocked, we...
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    About this property
    Beech Tree Cottage is a charming two-bedroom, one-bath guest cottage conveniently located in the historic district of Sag Harbor, NY - a 5-minute walk along the waterfront to Main Street and the center of the village. The beach is a short drive or bike ride away. The owners are full-time residents...
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    Location Information
    11963, Sag Harbor, Hamptons
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Vacation complete renovated great for entertainment1 / 21
    (2)Terrible
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
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    • Private Garden
    • Secure Parking
    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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    Location Information
    11978, Westhampton Beach, Hamptons
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Private Garden
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (SUMMER 2018 HAS BEEN FULLY RENTED, SORRY.) Lovely 3 bedroom, 3bath home in ideal location close to town and beaches, with secluded 20X40 heated pool and trilevel decking, edged by reserve and surrounded by greenery. Decking includes gazebo with large dining table, built in barbecue...
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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Location Information
    11930, Amagansett, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    East Hampton Classic1 / 22
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Grill
    • Air Conditioning
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    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2017
    We had a wonderful time at the house. The facilities were excellent, and John made an extra effort to accommodate our needs for Christmas dinner preparation. We particularly...
    Reviewed 14 October 2017
    My wife and I stayed here for four nights. The house was very nice. The pool was a nice extra; even though we didn't use it. The location was secluded and very serene. John, the...
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    About this property
    Located down a winding drive in the town of East Hampton our four bedroom home was constructed in the classic Hampton's style with cedar shingles and white wood trim. Sited on an acre and a half in the Northwest Woods, beautifully landscaped and private with close to 20 acres of reserve land...
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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Luxury Hamptons Vacation Home w/NEW Pool, Tennis Court, Hot Tub1 / 32
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Patio
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    • Hot Tub
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS TURNKEY PROPERTY HAS SOME OF THE BEST AMENITIES IN THE HAMPTONS. MANY OF THE IMPROVEMENTS WERE COMPLETED IN THE LAST TWO YEARS! Compare us with other area properties: - FRESHLY PAINTED EXTERIOR IN 2017 - HOUSE IS FULLY UP TO CODE, INCLUDING EGRESS WINDOWS IN LOWER LEVEL BEDROOMS FOR YOUR...
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    Location Information
    11727, Quogue, Hamptons
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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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
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    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
    11978, Westhampton Beach, Hamptons
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect place to spend your vacattions! Located on the south shore of Long Island, 20 minutes from JFK Airport. Walk to the Long Island Railroad connecting to Air-train JFK. A 40 min train ride to NYC Penn Station! Enjoy all that summer has to offer! A 10 minutes drive to Long Beach, Jones...
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    Location Information
    11520, Freeport, Long Island
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Romantic Getaway in Southampton (private room/bathroom)1 / 14
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2018
    Great location. Beautiful grounds. Gracious host. The home was easy to find, peaceful and located in an area of that made getting around central Long Island simple and...
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    About this property
    Newly renovated house with nice spacious rooms with comfortable new double beds. Double occupancy room /private bathroom/entrance, queen size bed newly renovated 4 bedroom-3 bathroom home in prime Southampton location. Close to bay, beach and town. Directly across the street from the fascinating...
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    Location Information
    11968, Southampton, Hamptons
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Waterfront
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    • 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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    Location Information
    11946, Southampton, Hamptons
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
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    • Washer
    • Hot Tub
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    • Private Outdoor Pool (Unheated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located in Southampton. It has 4 bedrooms and sleeps 10. If you have been wanting to visit the Hamptons this house is the perfect choice since it’s perfectly located in the heart of the Hamptons. Just a three minute drive to the village and 5 min drive to the famous Coopers...
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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/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
    This 5 bedroom has been added on and renovated throughout the years, and is bright and sunny with high ceilings and large window in the living room. Through the front door you will find a spacious living room, with wood burning fireplace and dining area to enjoy large groups. There is one half...
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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    Royal Atlantic Beach Front Resort , Montauk 1 Bedroom Suite For Rent Minimum of 2 Night Stay Sleeps 4 126 S Emerson Ave, Montauk, NY 11954 ONE BEDROOM VIP SUITE: Located directly across the street from the beach. It has a private balcony facing the pool courtyard. This suite features an open...
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    Location Information
    11954, Montauk, Hamptons
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    East Hampton Luxury Home  PERFECT FOR FAMILIES1 / 34
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful summer home sits on an acre property only 3 years old and newly painted and furnished by Perter Andrews. It has a salt water heated pool, new cedar children's jungle gym with swing set, elevated ceder deck, dining room that seats 10, Eat-in kitchen that seats 8, fireplace with...
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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
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    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house has it all! 3 bedrooms with plenty of space for addition guests to sleep in the den. 2 bathrooms. Big living room, dining room, eat in kitchen. The den boasts a large screen TV with surround sound. Patio with furniture and gas grill. Heated pool! Dish washer in kitchen. Washing machine,...
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    Location Information
    11951, Bellport, Long Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Hamptons private beach front home + pool1 / 17
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Ocean Views
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly refurnished and upgraded Hamptons Beach House. Amazing bay views from every room. Heated pool and private sandy beach. Ideal for large families. Swim in the bay or your own pool. This home is on the border of Shinnecock Hills and Hampton Bays making it very desirable due to its...
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    Location Information
    11946, Hampton Bays, Southampton
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Washer
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    • Hot Tub
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    • Cable/satellite TV
    • Patio
    • Balcony
    Suitability
    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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    Location Information
    11976, Water Mill, Hamptons
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Garden
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    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape from everything at a private beach with gorgeous sunsets or dive into the backyard pool for a refreshing swim. Bright, open floor plan features a new kitchen and ample decking with an outdoor shower. Featuring 3 bedrooms and 2.5 brand new bathrooms. Wood burning fireplace in main living...
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    Location Information
    11937, Springs, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy acre beautiful parcel sits this updated light filled home in a Development with wide street for walking. With 4 Master Ensuite bedrooms, spacious with 2 masters with king beds and private baths, one with queen bed and private baths and the other with two twin beds and private bath...
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    Location Information
    11963, Sag Harbor, Hamptons
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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