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Holiday Rentals in Long Island, NY

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    Travellers to Long Island are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 14
    5 of 5 bubbles (3) Excellent
    Montauk
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    1 / 55
    5 of 5 bubbles (7) Excellent
    Southampton
    7 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    1 / 12
    East Setauket
    5 Bedrooms, 8 Bathrooms, Sleeps 10 | Quick View
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    1 / 13
    Sagaponack
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    With the ultimate prime Hamptons location, and the comforts of home, this vacation rental is an excellent value for all types of friends and family retreats. The outdoor areas are newly designed and rebuilt with 3,100 square feet of mahogany decking. Right outside the great room there is a new... View all property information
    Location Information
    Sagaponack, Hamptons 11962
    1 / 14
    Cutchogue
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This newly renovated cottage has a spacious living room, large eat-in-kitchen, 2 bedrooms; one with queen-sized bed, the other with two twins, and one full and one half bath. There is a waterview across the street from the relaxing 'pebble lounge' the garden seating area in front of the house.... View all property information
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    Cutchogue, North Fork 11935
    1 / 24
    Amagansett
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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, this classic five bedroom, four and one-half bath traditional has every amenity and plenty of style. There's lots of open space for living including a lovely great room... View all property information
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    Amagansett, Hamptons 11930
    1 / 12
    Kismet
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This house is perfect for a large family or a couple of families to enjoy the laid back beach vacation Kismet offers. The bedrooms are spacious and there is a large outdoor deck perfect for barbecues and family dinners. There is an upper deck with partial view of the ocean and lighthouse.... View all property information
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    Kismet, Fire Island 11706
    1 / 23
    Cherry Grove
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
    Location Information
    Cherry Grove, Fire Island 11742
    1 / 13
    Bridgehampton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful contemporary home set on 1.6 private idyllic acres. Walk to town, near beaches. Easy drive to Sag Harbor, Southampton and East Hampton. Right by Hampton Classic and Polo grounds. New designer furnishings and linens. Separate master suite with Jacuzzi and steam shower. 3 Additional... View all property information
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    Bridgehampton, Hamptons 11932
    1 / 16
    Bridgehampton
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This spacious, renovated 5-bedroom, 4-bath home is on a secluded 1/2 acre, with a 200-foot private driveway leading to the wonderful, bright residence. The house backs onto a community reserve, so there is complete privacy in the pool, decks, and backyard. On the main level, there are 4 bedrooms... View all property information
    Location Information
    Bridgehampton, Hamptons 11932
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    1 / 36
    Sag Harbor
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    5 bedrooms, 4.5 full baths. New construction, steps to private beach. Bathrooms of Carrara marble and polished chrome finishes. Open living/dinning and family room with 2 fireplaces. Mahogany deck and beautiful 20x40 Gunite heated pool with Danish brick patio. Gourmet country kitchen with... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 21
    Fair Harbor
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
    Location Information
    Fair Harbor, Fire Island 11706
    1 / 21
    North Fork
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    A renovated home in the heart of the North Fork near the beach and several wineries. Please inquire about weekends, weeks or monthly/summer rental for 2015. Sleeps 8<BR><BR>Enjoy a bright renovated home with 12 skylights, cathedral ceilings and entirely new furnishings only ¼ mile to Cutchogue... View all property information
    Location Information
    North Fork, Long Island 11956
    1 / 13
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    RENTAL REGISTRY # 16-1,869 This cottage is located on one of the nicest blocks in Springs area of East Hampton. The house is a cozy ranch, with a Cathedral ceiling in the living/dining area. Relax on our lovely deck surrounded by lawn, trees and gardens and just watch the birds as you sip a drink.... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 16
    5 of 5 bubbles (1) Excellent
    Sag Harbor
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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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... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 18
    5 of 5 bubbles (2) Excellent
    East Hampton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Desirable Northwest Woods home close to East Hampton Village, ocean and bay beaches and Sag Harbor. Access to community association park on Hands Creek - lovely private view with Adirondack chairs. Walk to Hands Creek and Settlers Landing. Short drive to Cedar Point Park with picnic grounds,... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 22
    Sound Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautiful home has an open floor plan for dining and entertaining with spectacular water views from every room. The beach is pristine and the area is quiet and family friendly. It is perfect for swimming, fishing, walking or just enjoying nature. There is an outside deck with a table and... View all property information
    Location Information
    Sound Beach, Long Island
    1 / 9
    Southampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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,... View all property information
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    Southampton, Hamptons 11901
    1 / 13
    Snyder Square
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Fully furnished two bedrooms, central HVAC, back porch, back yard, . Accessible to public transportation. Families & Professionals welcome. Definitely a home away from home. Plenty closet space One Queen bed. Two twin beds, convertible to a King bed. View all property information
    Location Information
    Snyder Square, Long Island 11203
    1 / 33
    5 of 5 bubbles (5) Excellent
    Hampton Bays
    7 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    Huge 7 bedroom contemporary with 4 1/2 baths, huge deck, in-ground pool, outdoor bar, 7 person hot tub, gas BBQ. Spectacular recreation room, wonderful for entertaining. Fully loaded kitchen, 10 minute drive to ocean beach, near restaurants, clubs and all. This luxury home is available for... View all property information
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    Hampton Bays, Hamptons 11946
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    1 / 24
    Hampton Bays
    8 Bedrooms, Sleeps 20 | Quick 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... View all property information
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    Hampton Bays, Hamptons 11946
    1 / 16
    Baldwin
    2 Bedrooms, 1 Bathroom, Sleeps 2 | Quick 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... View all property information
    Location Information
    Baldwin, Long Island 11510
    1 / 23
    5 of 5 bubbles (3) Excellent
    Hampton Bays
    7 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    Only 600 feet from one of the most beautiful (private) Hampton's beach. Enjoy poolside living in this stunning contemporary home complete with lots of skylights and cathedral ceiling. Bike along the Peconic Bay or enjoy miles of sandy beach just steps away. This spacious home has a large heated... View all property information
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    Hampton Bays, Hamptons 11946
    1 / 11
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Enjoy the work of a renowned local architect who has turned this traditional East End shingle house into a sleek modern heaven. You will enjoy the quietness of the neighborhood while taking advantage of easy access to all the activities that this wonderful area offers. Several beaches are within... View all property information
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    East Hampton, Hamptons 11937
    1 / 17
    Peconic
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Enter a world of tranquility and surround yourself with the beauty of nature!<BR>Decorated with an eclectic mix of antique and contemporary furniture, the home has three bedrooms, one bath, dining room, living room with large flat screen tv, sunroom with seating and dining area. Kitchen is... View all property information
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    Peconic, North Fork 11958
    1 / 19
    East Hampton
    6 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    About this property
    Located in the exclusive Wainscott hamlet of East Hampton and situated between East Hampton Village with its world renowned shopping and beaches, and the historic village of Sag Harbor; this 6 bedroom, 3.5 bath post-modern home comfortably sleeps 10 and is ideally located on a private cul-de-sac... View all property information
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    East Hampton, Hamptons 11937
    1 / 18
    5 of 5 bubbles (3) Excellent
    Orient
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Enjoy gorgeous water views of Gardiner's Bay from this immaculate Victorian home situated on 1 acre. This spacious and beautifully decorated home comfortably accommodates 8 adults. Beds: 1 King Bed, 2 Queen Beds, 1 Double Bed View all property information
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    Orient, North Fork 11957
    1 / 18
    5 of 5 bubbles (1) Excellent
    Glen Cove
    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Beautiful home close to beaches, parks and less than 1 hour via nearby train to NYC. The original "Gold Coast" Glen Cove and the surrounding areas of Locust Valley, Sea Cliff, Oyster Bay, Lattingtown, Bayville and the Brookvilles. Playground for the rich and famous, who prefer to keep a low... View all property information
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    Glen Cove, Long Island 11542
    1 / 8
    5 of 5 bubbles (18) Excellent
    Port Jefferson
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    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... View all property information
    Location Information
    Port Jefferson, Long Island 11777
    1 / 17
    East Hampton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    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... View all property information
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    East Hampton, Hamptons 11937
    1 / 17
    Hampton Bays
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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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... View all property information
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    Hampton Bays, Hamptons 11946
    1 / 19
    Wainscott
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Our home is a great retreat with everything that you need to relax and enjoy your time with family and friends. The spacious interior along with the large outdoor pool and yard area is a great space for entertaining. The home is close to everything… as it is centrally located in the hamlet of... View all property information
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    Wainscott, Hamptons 11975
    1 / 18
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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... View all property information
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    Greenport, North Fork 11944
    1 / 32
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    May September weeks $1900 October-April weeks $900 RENOVATED WITH BEAUTIFUL WATER VIEWS. ACCESS TO CLEARWATER BEACH A MEMBERS ONLY PRIVATE BEACH, PICINC, BARBQUE AND CHILDRENS PLAY GROUND IS INCLUDED IN YOUR RENTAL RENT INCLUDES ALL TAXES, UTILITIES AND CLEANING FEE OF $180. SEPARATE $600 FULLY... View all property information
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    East Hampton, Hamptons 11937
    1 / 16
    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Historic home in Greenport Village walking distance to restaurants, water, shopping etc..bike or short drive from vineyards. Large yard with outdoor patio with BBQ and outdoor shower. 2 family home with two separate duplex units that can be rented separately or together. Perfect for family... View all property information
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    Greenport, North Fork 11944
    1 / 22
    5 of 5 bubbles (2) Excellent
    East Hampton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This spacious Cape Cod design features four large, exquisitely furnished bedrooms, two full baths, stunning eat-in kitchen, sunny family/living room with fireplace, and separate dining room. A swimming pool, central air-conditioning, and high speed wireless internet access are just some of its... View all property information
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    East Hampton, Hamptons 11937
    1 / 14
    Hampton Bays
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Your own private summer resort. This house has it alll, you won't want to leave! Waterfront dock, jacuzzi, sparkling pool, multiple patios, 2 outdoor grills, and multiple balconies are key outdoor features. State of the art kitchen, large country dining room table, 2 fireplaces, 2 open airy... View all property information
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    Hampton Bays, Hamptons 11946
    1 / 18
    Bellport
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Bellport, Long Island 11951
    1 / 19
    5 of 5 bubbles (1) Excellent
    New Suffolk
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Wi-Fi
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    • Private Garden
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Short walk to the most gorgeous bay beach, restaurants and marina. This adorable spotless 2 bedroom beach cottage sleeps 2-5 people and has a fully equipped kitchen with dishwasher, gas stove/oven, refrigerator with freezer, cozy living room with sleeper sofa and plenty of seating, tv, cable,... View all property information
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    New Suffolk, North Fork 11956
    1 / 20
    Shelter Island
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Large Shelter Island Farmhouse<BR>Beautiful Shelter Island is the most enjoyable, preserved, natural beauty on the North Fork and is yours to explore. Relaxing is mandatory...<BR>The farmhouse is close to all - steps from the golf course and beach<BR>46 West Neck Road - overlooks Town Golf Course+... View all property information
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    Shelter Island, Hamptons 11965
    1 / 14
    Fire Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
    • Terrace
    • Satellite TV
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    • Grill
    • Balcony
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Fire Island is a 35mile long barrier island located just off the South Shore of New York's Long Island. It is an island of many diverse communities. The house is located in a community called Lonelyville, one of the oldest on Fire Island. There are no cars permitted on Fire Island, the house comes... View all property information
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    Fire Island, Long Island 11706
    1 / 8
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • ?
    • Smoking allowed
    • x
    About this property
    Historic Greenport Village has been recently renovated and is in walking distance to all. This is a 2 family home that can be rented separately or together. Pricing here is for house 2. One bedroom has a queen and the other can be configured as a king or two twins. Parking, beach access, convenient... View all property information
    Location Information
    Greenport, North Fork 11944
    1 / 26
    5 of 5 bubbles (1) Excellent
    Mattituck
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Four bedroom/2 bathroom cozy cottage located in the heart of the North Fork. Offers 3 bedrooms and 1 bath in main house with separate guest quarters including guest room loft and private bath. Includes outdoor shower, firepit, large bbq with fridge and outdoor dining with fireplace area. Centrally... View all property information
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    Mattituck, North Fork 11952
    1 / 15
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    AVAILABLE Summer and Beyond. Wonderful, delightful, story book style cottage with white picket fence for your vacation pleasure ! This adorable 4 bedroom home is fully renovated, charming shabby chic decor. There is a heated pool and large driveway. BRAND NEW OUTDOOR SHOWER for sun-watering your... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 36
    Sound Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Grill
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    • Parking
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our two homes are next to each other with spectacular views of Long Island Sound. Each home has 2 bedrooms, 2 bathrooms and one sofa bed. Both houses have open floor plans and together can comfortably accomodate 12 people. Both homes are new construction with all new appliances and furniture. There... View all property information
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    Sound Beach, Long Island
    1 / 31
    5 of 5 bubbles (1) Excellent
    Hampton Bays
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    For families w or w/o kids or group adults over 30 years old up to max.8 guests inquire with your specific details for availability. Min.2 nights JUN or SEP, 3 nights for Memorial Day or Labor Day, 4 nights for JUL-AUG. EXTRA at check-in: 180$ cleaning fee + refundable sec.deposit up to 48h... View all property information
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    Hampton Bays, Hamptons 11946
    1 / 41
    Montauk
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Porch
    • Shared Garden
    • Grill
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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... View all property information
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    Montauk, Hamptons 11954
    1 / 11
    Westhampton
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This 3 bedroom, 2 bath ranch house is in excellent condition and is newly furnished for comfort, style, and flexibility. Sitting on 1.5 acres the house is very secluded and private and just a short drive to West Hampton Beach and many beautiful beaches and parks. There bedrooms feature Tempurpedic... View all property information
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    Westhampton, Hamptons 11977
    1 / 37
    Amagansett
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Sauna
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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,... View all property information
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    Amagansett, Hamptons 11930
    1 / 8
    Sag Harbor
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    NEW CENTRAL AIR CONDITION WITH NEST THAT KEEPS HOUSE KOOL AT ALL TIME .PRICELESS!! All room have the own TV's. All Beds are memory form and super comfortable .house is very clean wit all new linens. 2 ned bathrooms.great home feeling in a family neighborhood. you can walk or walk into town main st... View all property information
    Location Information
    Sag Harbor, Hamptons 11963