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Long Island Vacation Rentals

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    Travelers to Long Island are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    1 Bedroom, Sleeps 2Quick View
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    Modern 3+ Bedrm/2.5 Bathrm with 70' WATERFRONT in luxurious Water Mill. Leave your car home! 2 Minute stroll to Village for bagels in the morning and Suki Zuki sushi (restaurant) in the evening. Bike/Walk to Ocean/Beach (1.5 Mile). 5 minute walk to Luxury Hampton Jitney Bus from Manhattan. New...
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    Water Mill, Hamptons 11976
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    One large fishing cabin from the 20's has been redesigned and renovated with upcycled materials for contemporary loft style living with a Mediterranean touch. 3 bedrooms, 2 bathrooms (claw foot bathtubs), and a loft style common room with cathedral ceiling. Concrete floors and antique tiles keep...
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    Montauk, Hamptons 11954
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    18 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    A true retreat! Peace and serenity....these will be your thoughts as you look out and view the harbor and magnificient woods located on 3 acres! We are minutes away from a very lively town with many restaurants, theatre and shopping! We have beautiful restaurants on the water as well!! This...
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    Port Jefferson, Long Island 11777
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, Sleeps 10Quick View
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    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
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 2Quick View
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    Luxurious 2 bedroom on an ultra quiet cul de sac. 1 mile to LIRR. Close to all amenities . All inclusive. Furnished with the most luxurious furniture, enjoy, 55 inches and 37 inches LED., wi if printer, Xbox one, Wii system, Bose system, netflix, amazon instant video, cable , parking, beautiful...
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    Baldwin, Long Island 11510
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 2
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    2 Bedrooms, Sleeps 6Quick View
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    This newly renovated cottage in the heart of Montauk is 1000 feet from the ocean beach. It is a free standing cottage with a large back yard for entertaining. It has been in our family for over 70 years. It has central heat and air, with hard wood floors and modern. It is located between the...
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    Montauk, Hamptons 11954
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 7Quick View
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    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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    East Hampton, Hamptons 11937
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    Updated North Fork home located in the beautiful wine country of Long Island. Gourmet kitchen, perfect for entertaining. Luxurious master Suite with spa-like shower. Living room and each bedroom has its own TV. Rec-room located on separate level, great for kids & privacy. Gas barbecue, outdoor deck...
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    Aquebogue, Riverhead 11931
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Charming, private, 2 story cottage with outdoor balconies. "Treehouse" feel with great wooded views. Queen bed, full bath, hardwood floors. Sitting area in first floor with washer/ dryer. Covered balcony with gas firering, warm and cozy! Amazon / Netflix Surrounded by nature preserve and...
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    East Hampton, Hamptons 11937
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    8 Bedrooms, Sleeps 20Quick View
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    Sunsets on the Beach, Walk in the Woods Inspired by Walden, Thoreau and Emerson, Shell House is the quintessential luxury rental in the Hamptons. Dock in the nearby marina or rent a boat for the day. Shell House is your gateway to world class fishing, sprawling vineyards and quaint villages...
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    Hampton Bays, Hamptons 11946
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    About this property
    Try finding another rental so fully-stocked with all of the comforts you're used to in your own home! <BR><BR>This is a beautiful and cozy Montauk beach home, newly-renovated with clean, hardwood floors, spacious living area and kitchen. This house includes an awesome deck, complete with full...
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    Montauk, Hamptons 11954
    Rental Home - 3 Bedrooms, 5 Bathrooms, Sleeps 6
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    Victorian Seasons is a unique historic property. All work is of excellent craftsmanship and is historically accurate in restorations. This one bedroom apartment features a kitchen with stove/oven, refrigerator and necessary utensils. The bathroom is new and designed to evoke the 1930's charm of...
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    East Marion, North Fork 11939
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    5 Bedrooms, Sleeps 1Quick View
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    It's Private room in commack long island NY My place is close to nightlife, the airport, the city center, 2m to commack library 12 m to the beach it's on the central of long island place is close to nightlife, the airport, the city center, parks, public transport Robert Moses state park Robert...
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    Commack, Long Island 11725
    Private Room - 5 Bedrooms, 3 Bathrooms, Sleeps 1
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    6 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    Adorable 2 bedroom cottage sleeps 4 1000 ft to private beach! All new paint Full kitchen. New bathroom Master BR w/ queen bed , a/c,ceiling fan ,flat screen TV . 2nd BR w/ 2 twin beds. Living room with a/c, flat screen TV with netflix.<BR>Wireless Internet. Living room opens to to large screened...
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    Baiting Hollow, Long Island 11933
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    This is a lovely older home with modern amenities. Great for a family reunion, get together with friends and for visiting the North Fork and South Fork of Eastern Long Island. This spacious home is ideally located. Five minutes to Ocean beaches, Shinnecock Bay restaurants and shops, 15 min to...
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    Hampton Bays, Hamptons 11946
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10Quick View
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    About this property
    This home is perfectly located in Southampton. It is a 4 Bedroom, sleeps 10. If you have been wanting to visit The Hampton's for the first time this house is the perfect choice since its perfectly located in the heart of the Hampton's, just a three minute drive to the village with all the...
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    Southampton, Hamptons 11968
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    The Space Located in Southampton less then a half a mile from the quite beaches of Peconic Bay, this house is also just a 10 minute drive to Sag Harbor or Southampton Villages. Close to ArtHampton (5 mi), Art Market (5 mi) and Hampton Classic Showgrounds (6.5 mi)! The house has 4 bedrooms, three...
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    Southampton, Hamptons 11968
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 9Quick View
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    The Sea Breeze House is located in the enchanting community of Sag Harbor. The house is located walking distance to the only private beach in the Hamptons. You can walk or bike to town. Grab a bottle of wine head to the beach and enjoy the amazing sunset on the east end, sit on the porch relax and...
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    Sag Harbor, Hamptons 11963
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    About this property
    Brand New Chic Saltwater Dark Bottom Pool with Tanning Ledge! Whisper quiet retreat for all seasons in updated contemporary saltbox in East Hampton's NW Woods. Close to beach and charming EH and Sag Harbor! Rental contract required. RR # 161918 Also has wood burning fireplace and firewood...
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    East Hampton, Hamptons 11937
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    This is 4BR/3Bth contemporary house located in the Springs off Three Miles Harbor Rd, 4.2 miles from Citarella. Steps to Gardiner's Bay. Swimming pool, outside shower, deck, cable TV, fireplace, Wi-Fi. Two master bedrooms on the 2nd floor w/two full bathrooms. Two bedrooms on the first floor - must...
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    East Hampton, Hamptons 11937
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide 2 comfortable...
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    Southold, North Fork 11971
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 10Quick View
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    This home has been fully renovated and has been meticulously furnished. 3 bedrooms and 2 modern bathrooms Modern eat in kitchen with butcher block counter & breakfast bar Sliding doors out to large backyard 1 queen bedroom 1 bedroom with 2 fulls 1 master suite with wet bar and additional private...
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    East Hampton, Hamptons 11937
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    Heated Pool, Fireplace, Finished Basement, 3 Bedrooms, and 2 Baths. Located approximately 1000 feet from the beautiful beach is this wonderful and amazing 3 bedroom, 2 bath, beach house featuring living room with fireplace, finished basement, in-ground heated pool. Great price for this one of a...
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    Amagansett, Hamptons 11930
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    DIAMOND BEACH HOUSE ,IS LOCATED IN THE CULLEN SHORES AREA.ONE BLOCK, TO PRIVATE BEACH . HOME HAS TWO DECKS, NEW APPLIANCES ,CEILING FANS THREW OUT. .AND AC IN BACK ROOM SLEEPS 9 .OUTDOOR SHOWER. PRIVATE BACKYARD .THERE IS THE CROWS NEST LOOKOUT, OF THE SOUND .AMAZING SUNSETS TO ENJOY. CIRCULAR...
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    Montauk, Hamptons 11954
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, Sleeps 6Quick View
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    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 2Quick View
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    About this property
    Hello, I am a Supper Host on other sites, want to make your stay pleasurable. (`ROOM RENTAL ONLY') ...In a 3 bedroom Ranch Home...Cozy Zen Artist quite home ,Get away from all the noise or hectic life style want to try country living ...Romantic Nite sitting by the fireplace having drinks. (One...
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    East Quogue, Hamptons 11942
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    4 Bedrooms, Sleeps 8Quick View
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    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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    Southampton, Hamptons 11968
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    The Sea Breeze House is located in the enchanting community of Sag Harbor. The house is located just steps from the only private beach in the Hampton. You can walk or bike to town. Watch the sunset from the front porch, enjoy the evening sea breeze. The Space: The Sea Breeze House is a chic,...
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    Sag Harbor, Hamptons 11963
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 12Quick View
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    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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    6 Bedrooms, Sleeps 12Quick View
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    This home is perfectly located in Southampton. The house is nestled in a park like setting with a private tree-lined yard. You will have all the privacy you want. Enjoy a beautiful built in pool with hot tub. The home is clean, stylishly decorated, and steps away from a gorgeous nature preserve. (...
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    Southampton, Hamptons 11968
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, Sleeps 10Quick View
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    ​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
    Rental Home - 5 Bedrooms, 8 Bathrooms, Sleeps 10
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    This home is perfectly located a few blocks from Wollfer Vineyard and blocks away from the town of Sag Harbor. You will have all the privacy you want. Enjoy a beautiful built in pool. The home is clean, stylishly decorated, and close to gorgeous beaches. Work out room, everything! The location...
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    Sag Harbor, Hamptons 11963
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, Sleeps 7Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Sag Harbor, Hamptons 11963
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Pet friendly
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    About this property
    My wife and I have a quaint country/beach house with new furniture and a fresh coat of paint. We have furnished our home with our love for the ocean and the country. Terra cotta tiles and farm style kitchen table with bench and chairs in the kitchen. Living room with brand new Pottery Barn...
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    Hampton Bays, Hamptons 11946
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Wi-Fi
    • Waterfront
    • Satellite TV
    • Private Outdoor Pool (Unheated)
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    • Ocean Views
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Fire Island Pines. A gay community that is friendly to all. Beautiful beaches, great clubs, serenity steps from the beach. A view of the ocean from every room. Great for entertaining, or a quiet repose. All amenities included. A seven minute walk to the harbor. Enjoy a place...
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    Fire Island Pines, Fire Island 11782
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Hot Tub
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    Pet friendly
    Kid friendly
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    Traditional two-story featuring 4 bedrooms, 3.5 bath, gourmet kitchen, Jacuzzi and heated pool. This home is a perfect summer getaway. You do not only get to enjoy your summer vacation with the beaches, good food and shopping nearby, but the house itself offers you amazing amenities to enjoy summer...
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    Bridgehampton, Hamptons 11932
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    • Central Heating
    • Terrace
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have your coffee with the sunrise and your wine with the sunset from the expansive deck overlooking the waves. Location Location Location! We are right on the beach! House is meticulously maintained - very clean and well designed for extended family vacations. We provide bicycles so you can...
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    Ocean Bay Park, Fire Island 11770
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    • Internet Access
    • Grill
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    • Satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    5 bed 4 bath, heated pool, kid and pet friendly 5 bedroom, 4 bath, newly renovated home in Water Mill section of Southampton. Close to town and beaches, heated pool, kids play set, sand box and basketball hoop on close to an acre. Wood burning fireplace, new floors and modern kitchen with...
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    Water Mill, Hamptons 11976
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Secure Parking
    • Satellite TV
    • Private Yard
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the best season of the year in this lovely house in the heart of Bellport Village NY, an hour and half away from New York comfortably fit 2 adults and 2 child ( or 3 to 4 adults). The swimming pool makes it even more pleasant, like an oasis. This is a small house (800 sq/ft) with 2 bedroom...
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    Location Information
    Bellport, Long Island 11713
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sea Breeze House is located in the enchanting community of Sag Harbor. The house is located just steps from the only private beach in the Hampton. You can walk or bike to town. Watch the sunset from the front porch, enjoy the evening sea breeze. The Sea Breeze House is a chic, modern, yet...
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    Sag Harbor, Hamptons
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Washer
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    • Grill
    • Ocean Views
    • DVD Player
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    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterview Hampton home located in sought after Shinnecock Hills. 900 ft from Shinnecock bay with mooring rights. Which means you can basically keep your boat in your backyard of Shinnecock bay. 5min from Southampton village and ocean beaches. 5 star restaurants within walking distance. 1mile to...
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    Location Information
    Hampton Bays, Hamptons 11946
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Reviews
    4 Bedrooms, Sleeps 10Quick View
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    • Washer
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    • Housekeeping Included
    • DVD Player
    • Balcony
    • Satellite TV
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our house is an historic Dutch colonial, both cozy and spacious, with warm wood trim and wood floors throughout. The 20 x 20ft. Great Room, a perfect gathering space for family and friends is complete with a baby grand piano, cable TV, children's toys and books, classic novels and wood burning...
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    Location Information
    Greenport, North Fork 11944
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 4Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kitchen, two bedroom, two bath, washer, dryer, Wifi, flat screen tv, private rose garden, private parking, a kayak, two bicycles, public swimming dock at end of block, and is one...
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    Greenport, North Fork 11944
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, Sleeps 2Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Explore the historic seaport of Greenport Village from this recently remodeled 1-bedroom, 1-bathroom vacation rental apartment that comfortably sleeps 2. Located in the heart of downtown, you won’t find a better location to explore all the area has to offer than from this charming apartment. Only 2...
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    Greenport, North Fork 11944
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    33 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Terrace
    • Internet Access
    • Satellite TV
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As featured by New York Magazine, the Cliffside Resort entertains the perfect vacation! This 68 unit complex, located directly on the Long Island Sound with incredible sunset views, offers brand new 2 bedroom 2 bathroom luxurious accommodations. Cliffside Resort Waterfront Condominiums at...
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    Greenport, North Fork 11944
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Washer
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    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated house with nice spacious rooms with comfortable new double beds. Double occupancy room /private bathroom/entrance, queen size bed newly renovated 4 bedroom-3 bathroom home in prime Southampton location. Close to bay, beach and town. Directly across the street from the fascinating...
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    Location Information
    Southampton, Hamptons 11968
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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