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Long Island Oceanfront Vacation Rentals

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    Travellers to Long Island are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    24 Matching Rentals in Long IslandView all 447 rentals
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    Cutchogue Beach Cottage1 / 18
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Waterfront Hamptons Beach House w/ Dock, Hot Tub, & Awesome Views, Walk to Beach1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beach Cottage in Wine Country ,Walk To private bea1 / 20
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES1 / 17
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Central Heating
    • Balcony
    • Grill
    • Washer
    • Terrace
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 2016
    What a lucky find. This home has everything - location, setup and an owner to gives you complete backup for your holiday break.
    Reviewed 25 September 2015
    We had a wonderful time at Hickory House. The location in Southold is perfect for visiting the beach, wineries and farmers markets as well as Greenport and Mattituck. The home...
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    About this property
    3 bedrooms, 2 1/2 baths, sleeps 6 private Pristine, year round, vacation getaway, within 5 minute walk to two white, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, clean, smoke free home....
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    Southold, North Fork 11971
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Private Garden
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Beach, Fire Island, NY Summer Rental. Steps from beautiful ocean beaches, shops, restaurants, night life, ferries and all the Capital City of Fire Island has to offer. Credit Cards and Pay Pal Accepted. MINIMUM RENTAL 3 NIGHTS. See Photo inlay for VIDEO, AVAILABILITY...
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    Ocean Beach, Fire Island 11770
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Cozy North Shore Beach  House * Wine Country1 / 14
    (5)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Porch
    • Outdoor Dining Area
    • DVD Player
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2016
    This was an amazing get away. Loved the house, and the area. The beach was great and a short walk from the house. Quiet, friendly, and very clean park. Would definitely stay...
    Reviewed 16 October 2015
    We were looking for a quiet place to stay that accepted pets. The cottage was comfortable and had room for our grandchildren to stay with us. I loved that the beach was so close...
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    About this property
    Charming cottage in the woods just steps from the peaceful Long Island Sound. This cottage has two bedrooms and sleeps 4. One of the twin beds is on a our porch in a common area but it is indoors. See photo. New Kitchen counters and cabinets. Built in 1950, this cottage has been passed though two...
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    Baiting Hollow, Long Island 11933
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 February 2018
    Great accommodations, beautiful view, FANTASTIC SUNSETS, what’s not to like!As a repeat customer staying here in Spring, Summer and Fall I give stars.
    Reviewed 15 October 2016
    That's it! Unit was clean and comfortable. Beach was right there. Drive to town or spots of interest easily. Compact, well organized, nice little terrace overlooking the water...
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    About this property
    Overview: Waterfront Water's Edge suite, Suite C-204, accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. Quoted rental rates include all taxes, I do not charge resort fees...
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    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Adorable home with Large PRIVATE deck- Fire Island1 / 30
    (7)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2016
    Dennis was really helpful before with directions and how to get in the place.Everything was really clean and there were a ton of great things to help keep us like outdoor...
    Reviewed 9 September 2015
    I had never been to FI before, and neither had a bunch of my friends. We rented this house with not many expectations in mind but some beach time and needless to say, all of...
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    About this property
    Our wonderful cottage comes with all the expected amenities for the total vacation experience. It has two decks, a large private rear deck and fun smaller front deck for people watchers . Fire Island boasts no private cars in the summer until Sept 15 so the kids have freedom to wander safely after...
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    Location Information
    Kismet, Fire Island 11706
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    waterview house. rocky point. long island.New york1 / 33
    (7)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Private Garden
    • Porch
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2016
    My wife and I were looking for a quiet peaceful getaway to relax. We found exactly what we were looking for in this rental. We had the option of a sparcely populated beach on...
    Reviewed 25 September 2015
    Patty is the nicest person you will ever meet. Her house is in pristine condition and is positioned at a short walk from the sparsely populated private beach. Very relaxing and...
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    About this property
    Quaint 3 bedroom, 1 bath home, with beautiful views of the long island sound, and Connecticut, from the kitchen, dining area, bedroom, and back yard.Heat and Central air conditioning, cable, internet, Netflix,phone. electric stove/oven, toaster, coffee maker,microwave,convection toaster oven,...
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    Location Information
    Rocky Point, Long Island 11778
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Fair Harbor, Fire Island,NY  4 br house near the bay1 / 16
    (1)Very good
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Housekeeping Included
    • DVD Player
    • Grill
    • Private Garden
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2012
    I've been renting in Fair Harbor for over 20 years. What you need in a Fire Island rental is to be near the ferry, the store but still have and quiet and privacy. You need...
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    About this property
    Fair Harbor is on Fire Island in Suffolk county ny.. Imagine a barefoot community with wooden walkways great sandy beaches, great sunsets, wooden walkways... no cars... Sounds like paradise.. less than 2 hours from New york.. so close yet so far away. Our house is 1 house from the bay and is...
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    Location Information
    Fair Harbor, Fire Island 11706
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Ocean Views
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seasonal rental within a 5 minute walk to private beach, 5 minute drive to local horse riding farm and ten minutes drive to local north fork wineries. 10 minute drive to downtown Riverhead, Long Island rail road, outlets and restaurants.
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    Location Information
    Baiting Hollow, Long Island 11933
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Beautiful East Hampton Home / Heated Pool / Luxury Sheets and Towels1 / 21
    (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 three-bedroom home with large bedrooms and brand new modern Kohler baths. Large windows, modern/Art Deco furnishings, new kitchen, new washer and 2 dryers. Great quality towels, Italian sheets (by Frette) provided. Great beach towels (Jonathan Adler). Large 20x40...
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    Location Information
    East Hampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Porch
    • Central Heating
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CLEAN, QUIET, LARGE BEDROOM - GREAT DEAL - AFFORDABLE PRICE! One Queen Size bed that accommodates Two people Perfectly! Bright and Airy room! Large 52in Hunter Ceiling fan directly above the bed as well as soothing cross breezes from the oversized windows that overlook the sunny front garden....
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    Location Information
    East Hampton, Hamptons 11937
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is right on the sand, just a block away from a beautiful, uncrowded ocean beach in one of the world's most famous resort communities. Clean and comfortable, there is an upstairs deck off the living room and a downstairs patio off the eat-in kitchen, three bedrooms, two full bathrooms, a...
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    Location Information
    Amagansett, Hamptons 11930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Waterfront
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Resort style living in this fantastic private beachfront oasis in Sag Harbor Village. Enjoy fabulous views and amazing sunsets over Sag Harbor Bay from this wonderful 3 bedroom, 2.5 bath house with hot tub and sandy beach right in your backyard. Great family rental. Kids have their own private...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Outdoor Dining Area
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 waves by night and lounge on our oversized deck by day. This one of a...
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    Location Information
    Cherry Grove, Fire Island 11742
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Housekeeping Included
    • Washer
    • Terrace
    • Central Heating
    • Patio
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My home is located in a quiet neighborhood, just a short walk to the nearest ocean beach or town. For the beach, I have two beach carts, a wagon, lots of beach chairs, boogie boards, sand toys, etc. There are Tonka trucks to use at the beach or in the gravel driveway. BEACHES: KIRK PARK...
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    Montauk, Hamptons 11954
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Outdoor Dining Area
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Four Bed, four bath. Great for two families. + .Nice pool, basketball hoop, bikes, bogie boards, beach chairs, croquet, badmition, x box in basement, pool table, outdoor speakers, nice bar b que, great lounges by pool, big back deck close to Southampton beaches, close in hamptons. August 9th...
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    East Quogue, Hamptons 11942
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    7 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Sauna
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful estate home in Water Mill, New York borders the prestigious Matt Lauer's 40 acre horse farm with distant ocean views. This estate features 7 bedrooms with 7 en suite bathrooms, 2 1/2 baths, two master bedrooms. There are five full masonry fireplaces, pool room, wine room, cigar...
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    Water Mill, Hamptons 11976
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 10
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    Chic and Modern Beach retreat with heated Pool1 / 16
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Washer
    • Wi-Fi
    • Balcony
    • Grill
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2016
    This house has everything you need and is perfectly located. It is not far from Sag Harbour in a quiet area. Close to marina for kayaking and stand up paddle boarding. With...
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    About this property
    Privately situated on a park-like landscaped grounds, this classic 2 story French cottage was completely renovated for modern comfort and indoor/outdoor summer entertainment. This delightful house features an open-plan living room with fireplace, dining room, a gourmet kitchen with stainless...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beach house right on the sand, just a block away from a beautiful, uncrowded Atlantic Ocean beach. Clean and comfortable. Upstairs deck and downstairs patio off eat-in kitchen. Big living room, three bedrooms, two full bathrooms, washer and dryer, outdoor shower, gas grill, cable TV, internet...
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    Amagansett, Hamptons 11930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 bedroom 2 bath shingle home 1200 ft to secluded bay beach. Large dining with adjacent living room and sunroom. Family room with large tv and French door to garden. Outdoor shower nestled in bamboo. Wisteria covered pergola with teak table and seating. Well appointed home!
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    East Hampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Waterfront
    • Washer
    • Ocean Views
    • Housekeeping Included
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Price: $36,000 (June 15 to Labor Day) $17,000 (June) $18,000 (July) $29,000 (July through Labor Day) $20,000 (August through Labor Day) Neighborhood: Flanders Centrally Located West of Shinnecock Canal. Minimal traffic! Easy access to NYC and airports. Town of Southampton Lovely two-story Cape,...
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    Location Information
    Southampton, Hamptons 11901
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Waterfront
    • Grill
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An ideal spot for a comfortable, peaceful beach vacation. Our charming, renovated cottage is located in Lonelyville, on Fire Island a short drive or train ride from New York City. If you've never visited Fire Island you're in for a treat. Close to the city yet a galaxy away. There are no private...
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    Location Information
    Fair Harbor, Fire Island 11706
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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