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Holiday Rentals in Long Island, NY

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    1 / 16
    4 of 5 bubbles (1) Very good
    Fair Harbor
    4 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    1 / 20
    4.5 of 5 bubbles (7) Very good
    Shelter Island Heights
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 14
    3.5 of 5 bubbles (5) Average
    Baiting Hollow
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 28
    Southampton
    4 Bedrooms, 5 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Welcome to your private Hamptons escape! This immaculate Southampton vacation rental house is sure to provide the perfect vacation spot for your next family getaway. Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this gorgeous home is a terrific size and... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 11
    Montauk
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Ocean Views
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    About this property
    Situated on Montauk's most pristine stretch of oceanfront real estate, Gurney's Montauk Resort & Seawater Spa is a Hampton's icon and the only four-season resort in Montauk. With five unique dining and cocktail venues, guests can enjoy a wide range of dining options, from elegant seasonal cuisine... View all property information
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    Montauk, Hamptons 11954
    1 / 19
    5 of 5 bubbles (1) Excellent
    East Hampton
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 33
    Hampton Bays
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Hampton Bays, Hamptons 11946
    1 / 27
    Hempstead
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located within walking distance of The Garden City Hotel. The property is 15 Miles from Manhattan & just 25 Minutes from LaGuardia & JFK Whether you're in town for business or pleasure, This house allows you to enjoy our upscale accommodations at an exceptional value. Located just minutes from... View all property information
    Location Information
    Hempstead, Long Island 11550
    1 / 5
    3.5 of 5 bubbles (6) Average
    Montauk
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    About this property
    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... View all property information
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    Montauk, Hamptons 11954
    1 / 6
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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... View all property information
    Location Information
    East Hampton, Hamptons 11937
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    1 / 46
    Massapequa
    6 Bedrooms, 4 Bathrooms, Sleeps 19 | Quick View
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    About this property
    Hello! And thank you for your interest. This listing is for rental of the entire home which consists of 3 private apartments that can be used in unison for larger families or business travelers. This property can accommodate up to a total of 19 guests, 14 guests in beds/pullout sofas, and 5 guests... View all property information
    Location Information
    Massapequa, Long Island 11758
    1 / 19
    5 of 5 bubbles (9) Excellent
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This charming farmhouse is just what you’ve been looking for: A beautiful, newly renovated 1890's house with all the modern conveniences, perfectly located a few short blocks to Founders Landing Beach Park, Town Beach and Southold Village. About the House The house is a very bright and airy,... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 14
    5 of 5 bubbles (3) Excellent
    Montauk
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Shared Indoor Pool
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    • x
    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... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 23
    5 of 5 bubbles (3) Excellent
    Hampton Bays
    7 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    About this property
    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
    Location Information
    Hampton Bays, Hamptons 11946
    1 / 18
    5 of 5 bubbles (3) Excellent
    Orient
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    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
    Location Information
    Orient, North Fork 11957
    1 / 10
    5 of 5 bubbles (4) Excellent
    Sag Harbor
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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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... View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    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 / 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 / 20
    4.5 of 5 bubbles (2) Very good
    Bridgehampton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Top of the Line Double bed in a well appointed Bedroom with 2 closets, door in your bedroom to your private bathroom, for 1 or 2 people. BEAUTIFUL and COOL Hamptons Artist's home. CLOSE to ART FAIRS & EVENTS, CENTRAL LOCATION and VERY PEACEFUL, walk to town and to jitney or LIRR, restaurants,... View all property information
    Location Information
    Bridgehampton, Hamptons 11932
    1 / 6
    Fire Island Pines
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Just 90 minutes from Manhattan, but worlds away from NYC! In the Fire Island Pines, an idyllic gay community (but friendly to all) on the beach with no cars, just the deer roaming wild. The cabana is small but very self contained. BBQ on the deck overlooking the ocean. 5 minutes walk to "town"... View all property information
    Location Information
    Fire Island Pines, Fire Island 11782
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    1 / 31
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Charming, spacious, bright and quiet East Hampton home available year round, with a 2 night minimum stay now thru Memorial Day, and a minimum one week stay in the summer months. Bright & Sunny home has wood floors throughout, Cathedral ceiling in open living area with 3 skylights and 3 sets of... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 16
    East Hampton
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    Deliciously close to the shimmering bay, is this very special 5 bedroom, 4 bath shingled traditional beautifully sited on a serene 1.8 acre well-landscaped parcel in the desirable Grace Estate area between East Hampton and Sag Harbor. A distinctive coffered ceiling foyer leads to the vaulted living... 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 / 15
    1 of 5 bubbles (3) Terrible
    Westhampton Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
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    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.... View all property information
    Location Information
    Westhampton Beach, Long Island 11978
    1 / 11
    Amagansett
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Amagansett, Hamptons 11930
    1 / 27
    East Patchogue
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Gorgeous 2nd Floor Private entrance apartment with its own deck over looking the Great South Bay - Large bedroom - Bath & Living spaces , Kitchen w/washer dryer. All emendates, central heat & ac- w/internet , direct tv , private parking on 5 acres estate, 10 min to Village, train, 20 min Airport... View all property information
    Location Information
    East Patchogue, Long Island 11772
    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
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    East Hampton, Hamptons 11937
    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 / 21
    East Quogue
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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... View all property information
    Location Information
    East Quogue, Hamptons 11942
    1 / 23
    Amagansett
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | 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, 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 / 21
    Orient
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    About this property
    1,100 Square Foot house with 400 square foot deck in the backyard. House is part of community with rights to a private beach with a private barbecue/recreation area only a few minutes walk away. 10 minute walk to Orient Beach State Park which has the following activities: Biking,... View all property information
    Location Information
    Orient, North Fork 11957
    1 / 5
    3 of 5 bubbles (1) Average
    Montauk
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 24
    5 of 5 bubbles (1) Excellent
    Mastic Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This property is not a rental house; it is a wonderful retreat. On your first night you arrive to find a well appointed, carefully prepared home. There is a welcome basket, there are snacks and drinks in the fridge. We welcome you here to enjoy this beautiful escape from the hustle and bustle of... View all property information
    Location Information
    Mastic Beach, Long Island 11951
    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
    Location Information
    Glen Cove, Long Island 11542
    1 / 9
    East Quogue
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Contemporary home on an acre of wooded land. Amenities include central air-conditioning and heat, wood-burning fireplace, heated in-ground pool, fenced-in backyard, sunroom. Located near local and high-end shopping and dining, farm stands, beaches, wildlife reserve, hiking, and outdoor activities... View all property information
    Location Information
    East Quogue, Hamptons 11942
    1 / 33
    5 of 5 bubbles (2) Excellent
    Water Mill
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
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    • Pet-friendly
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    • x
    About this property
    This beautiful home is in a great location, was just renovated and is luxuriously furnished and thoughtfully appointed (including original art, and luxury linens, kitchenware and dishes new for 2016). Perfect for relaxation and entertaining, highlights include: -Large open concept family room... View all property information
    Location Information
    Water Mill, Hamptons 11976
    1 / 11
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Ocean Views
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Beautiful sunny home with south exposure. Large chefs kitchen. Spacious living room with flatscreen tv, baby grand piano and large french doors leading to a spacious deck. Four large bedrooms. Huge master bedroom with seating area and flatscreen tv. Large master bathroom with open air double shower... View all property information
    Location Information
    East Hampton, Hamptons 11942
    1 / 14
    Southampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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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... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 21
    Fair Harbor
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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 / 55
    5 of 5 bubbles (7) Excellent
    Southampton
    7 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    This is extravagant living at its best. Picture yourself enjoying expansive water views and majestic sunsets. The park like setting lends itself to an idyllic outdoor paradise. This home has 7 huge bedrooms and 5 palatial bathrooms. The house boasts a wide-open floor plan with soaring cathedral... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 25
    4.5 of 5 bubbles (6) Very good
    Hampton Bays
    9 Bedrooms, 4 Bathrooms, Sleeps 18 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Walk to beach. Enjoy sunsets over the bay in this beautifully designed contemporary central hall Colonial on 1.6 acres. Extremely large 9 bedrooms, 3.5 baths with state-of-the-art kitchen, formal dining room, large living room with fireplace and billiard room , ping pong room and full exercise gym.... View all property information
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    Hampton Bays, Hamptons 11946
    1 / 23
    Southampton
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    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” House, 5 bedrooms, 5 baths , CAC, hardwood floors, in-ground heated pool, Outdoor... View all property information
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    Southampton, Hamptons 11946
    1 / 12
    Kismet
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    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
    Location Information
    Kismet, Fire Island 11706
    1 / 24
    Hampton Bays
    8 Bedrooms, Sleeps 20 | Quick View
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    • x
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    • x
    About this property
    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 / 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
    Hampton Bays
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Large swimming pool (43' x 22' free form) with changing colors LED lights and water fall, a 10 people outdoor spa jacuzzi tub. Complete and well equipped outdoor kitchen, walking distance to the bay and 5 minutes drive to town or the OCEAN. Big and clean house in the woods. The house indulge... View all property information
    Location Information
    Hampton Bays, Hamptons 11946
    1 / 24
    Amagansett
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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, 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 / 16
    Levittown
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    LIVING STYLE: Come & go as you please without interacting with anyone else. The Bathroom & kitchen are right next to the Bedroom and are shared with a mom and daughter. The Washer and Dryer are available for your use. The house has a very large Country Kitchen, Living Room with a piano & and a... View all property information
    Location Information
    Levittown, Long Island 11756
    1 / 14
    5 of 5 bubbles (5) Excellent
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • x
    • x
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    • x
    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, flat screen TV and high speed wireless internet access and is... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 18
    Bellport
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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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