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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 / 22
    5 of 5 stars (1) Excellent
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 30
    Sag Harbor
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    1 / 14
    5 of 5 stars (3) Excellent
    Montauk
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    1 / 11
    Montauk
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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
    Location Information
    Montauk, Hamptons
    1 / 15
    Montauk
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    MONTAUK: EAST HAMPTON: SUMMER VACATION RENTAL: BEAUTIFUL HOME: BEAUTIFULLY FURNISHED Large, spacious and 5 Bedrooms, 5 Full Baths, Post-Modern Two Story Home nestled atop the Panorama Hills of Montauk between the Ocean and Long Island Sound. The Second Floor main living space includes a sun... View all property information
    Location Information
    Montauk, Hamptons
    1 / 13
    Long Beach
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Spacious home with 2 living rooms, a half-block to the beach! This beautiful, unique house is a huge 5 bedroom, 2 full bathroom, 2 living room beach home. Big front porch where you can gather after a day at the beach for BBQ and drinks. Bright, new kitchen with quartz countertops and dishwasher.... View all property information
    Location Information
    Long Beach, Long Island
    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
    Location Information
    East Hampton, Hamptons
    1 / 12
    East Setauket
    5 Bedrooms, 8 Bathrooms, Sleeps 10 | Quick View
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    About this property
    A wonderful summer getaway with stunning waterfront views, a few steps away from private beach access. This house sits on 2 full acres of land with steps leading down to the beach great for getting jet skiing, getting a tan or fishing, secluded from the busy streets of Long Island. Including a full... View all property information
    Location Information
    East Setauket, Long Island
    1 / 15
    Southampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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
    1 / 29
    East Hampton
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This beautiful 3-bedroom, 3.5 bathroom home in East Hampton sleeps 6 comfortably and won’t disappoint! You’ll never want to leave the 1-acre property, boasting modern amenities, a private outdoor pool and multiple balconies and decks! There’s plenty of room for you and your companions to sprawl... View all property information
    Location Information
    East Hampton, Hamptons
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    1 / 15
    East Hampton
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The house is clean and very modern with contemporary art hanging on the walls. The swimming pool and spa are surrounded by blue stone, lawn and geometrical stone walls. There is a grill and a garage. The rest of the property is filled with flowers, plants and trees. The master bedroom and bathroom... View all property information
    Location Information
    East Hampton, Hamptons
    1 / 6
    Remsenburg
    5 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    About this property
    19th Century house on 3 acres of gardens and fields. Traditional styling has been infused with modern touches and updates. Cook's professional kitchen, central air conditioning, jacuzzi, steam shower, heated swimming pool, internet and multi-room music system. Close to beach and recreation... View all property information
    Location Information
    Remsenburg, Long Island
    1 / 27
    Southampton
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Newly build home, no expense spared. Beautiful pool and outdoor dining and cooking/BBQ area. The prefect home for entertaining and relaxing. Fully equipped kitchen for cooking and dining, plenty of space for entertaining. Master bedroom is fit for royalty, 4 more beautiful bedrooms in main house.... View all property information
    Location Information
    Southampton, Hamptons
    1 / 6
    Westhampton Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Located on Dune road ocean side 100 feet to beach . Roof deck with great views of ocean and bay views Close to Main Street village and restaurants Available for your convenience kayaks and other toys Boat slip at municipal marina with ramp to load and unload boats or jet skies available located... View all property information
    Location Information
    Westhampton Beach, Long Island
    1 / 30
    5 of 5 stars (2) Excellent
    Quogue
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Quogue Village Modernist 4BR, 3BR recently renovated in rustic modern style. Huge chef's kitchen boasts 6 burner range, Gaggia espresso, Shun cutlery. Expansive 800sf pool, 8 person hot tub, 1.3 acres on quiet wooded cul de sac, and Quogue Village beach rights. View all property information
    Location Information
    Quogue, Hamptons
    1 / 17
    5 of 5 stars (9) Excellent
    Hampton Bays
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • x
    About this property
    Newly renovated home perfect for family get-away and for girls or guys week get-aways. As past owners of The Black Whale Motel in Hampton Bays for 16 successful years, we are well aware of what vacationers are expecting from their rental. We have tried to include everything needed to enjoy your... View all property information
    Location Information
    Hampton Bays, Hamptons
    1 / 12
    3 of 5 stars (1) Average
    Sag Harbor
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    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 Space: The Sea Breeze House is a chic,... View all property information
    Location Information
    Sag Harbor, Hamptons
    1 / 12
    Westhampton
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Our SeaBreeze Suite sleeps up to 4 guests in two rooms - one queen bed in private bedroom and two twin sized beds in living room - as well as a small kitchen w/ refrigerator, microwave, stove top oven and coffee maker. This suite also has free wifi, premium cable and private driveway... View all property information
    Location Information
    Westhampton, Hamptons
    1 / 13
    Ocean Bay Park
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
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    • x
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    • x
    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... View all property information
    Location Information
    Ocean Bay Park, Fire Island
    1 / 16
    Montauk
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Contemporary Chalet with pool, beautifully furnished, is now available for Montauk's most beautiful season of all … Indian Summer. Accepting reservations for Sept & Oct. 3 Bedrooms / 2 full baths + Outdoor shower Room. Huge wrap around cedar deck. AC in every room (never needed). Perfect central... View all property information
    Location Information
    Montauk, Hamptons
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    1 / 11
    East Quogue
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • ?
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    • x
    About this property
    This 4 bedroom, 2 bathroom contemporary is just steps away from a private beach and marina.<BR>Some amenities include:<BR>New granite kitchen<BR>Cathedral great room with flat screen tv<BR>Hardwood floors<BR>Multi level decking<BR>In ground heated pool<BR>Patio furniture and gas... View all property information
    Location Information
    East Quogue, Hamptons
    1 / 23
    4.5 of 5 stars (3) Very good
    Greenport
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
    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... View all property information
    Location Information
    Greenport, North Fork
    1 / 16
    4 of 5 stars (1) Very good
    Fair Harbor
    4 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • x
    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 by the bay is available for... View all property information
    Location Information
    Fair Harbor, Fire Island
    1 / 10
    4 of 5 stars (5) Very good
    Montauk
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Pet-friendly
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    • x
    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
    Location Information
    Montauk, Hamptons
    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
    Location Information
    Southampton, Hamptons
    1 / 20
    East Hampton
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Thank you for your interest in our newly renovated modern loft vacation home. Come be neighbors with designer Donna Karen and now our newest celebrity neighbor, Hugh Jackman in the NW Woods of East Hampton. 10 Minute drive to the village of East Hampton (6 miles) 10 Minute drive to the famous... View all property information
    Location Information
    East Hampton, Hamptons
    1 / 24
    Wading River
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Being one of our beach homes, this beautiful one bedroom is located directly on the beach. With a brand new kitchen and out door hot and cold shower! This home sleeps 5 people with sofa bed and cot. Everything is fully furnished with towels, linens and everything you would need. The only thing you... View all property information
    Location Information
    Wading River, Long Island
    1 / 11
    Ocean Beach
    4 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • x
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    • x
    About this property
    WE ARE OPEN FOR BUSINESS SUMMER 2015<BR>Thank you for your interest.<BR>Town rules require MINIMUM ONE-WEEK RENTALS.<BR><BR>This one-level house includes four bedrooms and one bathroom. It is for FAMILIES ONLY, AND NO PETS ARE ALLOWED(sorry, our daughter has serious allergies). Also, for the same... View all property information
    Location Information
    Ocean Beach, Fire Island
    1 / 13
    Snyder Square
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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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
    1 / 15
    East Hampton
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    • x
    • x
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    • x
    About this property
    Contemporary architect Bates and Massi built this one of a kind stylish dwelling in the Barnes Landing Area with very private and beautiful beaches.<BR><BR>Minimum stay is 1 week, no exceptions<BR><BR>House is a 5 minute short walk to the beach and a very short drive to the East Hampton... View all property information
    Location Information
    East Hampton, Hamptons
    1 / 19
    5 of 5 stars (9) Excellent
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    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
    1 / 25
    5 of 5 stars (1) Excellent
    Southampton
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    About this property
    Recently renovated, beautiful vacation home within a mile of Southampton Village restaurants and shops. It is located on a very quiet and private lane near two beautiful horse farms. This home features six large bedrooms and four and one half baths. The floor plan is open, bright and airy, with... View all property information
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    Southampton, Hamptons
    1 / 15
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    ARTISTS PRIVATE RETREAT- Just love your two week vacation time away at this beautiful, spacious and well appointed post modern home located conveniently to all beaches and East Hampton town. Professionally renovated and decorated for style as well as comfort . MOST 3 bedroom homes have all... View all property information
    Location Information
    East Hampton, Hamptons
    1 / 19
    Bridgehampton
    4 Bedrooms, 5 Bathrooms, Sleeps 9 | Quick View
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    • ?
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    • x
    About this property
    On a quiet shy 2 acre beautiful parcel adjacent to hundreds of acres of town reserve sits this updated light filled home with sweeping lawn, and reserves on 3 sides for complete privacy. Spacious with 4 bedrooms and 3.5 baths,Two masters with king beds and private baths, two additional bedrooms one... View all property information
    Location Information
    Bridgehampton, Hamptons
    1 / 22
    Southampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    ONE-OF-A-KIND VILLA NESTLED ALONG THE SHORE OF THE GREAT PECONIC BAY, with 180 degree views. The newly renovated and newly furnished (indoor as well as out) with all white interior consists of an open kitchen, living and dining area which lead to french doors, opening out to the beachside stone... View all property information
    Location Information
    Southampton, Hamptons
    1 / 17
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    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... View all property information
    Location Information
    East Hampton, Hamptons
    1 / 5
    Sag Harbor
    5 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Beautiful North Haven Minutes from Sag Harbor Village and Ferry to Shelter Island The heart of the Hamptons! Close to Bridgehampton, East Hampton, Southampton, Water Mill, Shelter Island. Walking distance from beaches and town. A park-like 2 acres with a man-made pond is the lush setting for... View all property information
    Location Information
    Sag Harbor, Hamptons
    1 / 19
    5 of 5 stars (4) Excellent
    Southold
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Porch
    • DVD Player
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Easy to reach, hard to leave! Relax in this charming setting overlooking one of the most beautiful vineyards on The North Fork, complete with a stunning and private sugar sand beach on Southold Bay, one of the best beaches anywhere on the North Fork or The Hamptons, yours to enjoy throughout your... View all property information
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    Southold, North Fork
    1 / 30
    Wading River
    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    Immerse yourself in the tranquility of New York’s Long Island area when you stay at this wonderful Wading River vacation rental home, called 'The Stella House,' ideally situated just steps from a spectacular private beach! With 4 bedrooms, 2 bathrooms and enough sleeping arrangements for up to 11... View all property information
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    Wading River, Long Island
    1 / 14
    5 of 5 stars (5) Excellent
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
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    "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
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    East Hampton, Hamptons
    1 / 15
    East Hampton
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
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    NORTHWEST WOODS - HALF A BLOCK TO THE BEACH This newly designed modern beach house is offered beautifully furnished inspired by Philippe Stark's white minimalist palette is located on a quiet lane in an upscale Northwest Woods neighborhood -- just four houses to Hedges Banks Drive and the private... View all property information
    Location Information
    East Hampton, Hamptons
    1 / 30
    5 of 5 stars (7) Excellent
    Sound Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
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    Located on the bluff with amazing views of the Long Island Sound around the year - This is our Waterfront Heaven. Set in a quiet neighborhood, the house is located on the bluff, about 85 feet above sea level. The house is facing the sea and the views are breathtaking. Conveniently located only... View all property information
    Location Information
    Sound Beach, Long Island
    1 / 26
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    Enchanted Garden setting is the perfect way to describe this Cottage that is walking distance to one of the most Beautiful Private Bay Beaches in the Hamptons! This immaculate home has three Bedrooms & two renovated custom designed bathrooms. You will be surrounded by Hydrangeas and Roses when you... View all property information
    Location Information
    East Hampton, Hamptons
    1 / 11
    East Hampton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    **Please click the 'Send email' button on the right for a detailed quote. (Please do not use book it.)** 2017 monthly rentals now open. Great summer rental in East Hampton. 4 bedrooms and 2 baths. Sleeps 8 comfortably (4 queen beds). •Modern, clean, and spacious •Quiet, comfortable, and peaceful... View all property information
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    East Hampton, Hamptons
    1 / 22
    5 of 5 stars (6) Excellent
    Montauk
    6 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • ?
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    East Hampton Rental Registry #16185 *** Please see Summer 2016 (May - October) availability, minimum stay requirements and pricing information at the end of this listing before contacting *** Thinking of spending time in Montauk? Great idea! Enjoy all the East End has to offer from the comfort of... View all property information
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    Montauk, Hamptons
    1 / 26
    5 of 5 stars (1) Excellent
    Mattituck
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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
    Location Information
    Mattituck, North Fork
    1 / 27
    East Patchogue
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    • x
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    • x
    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
    1 / 20
    Shelter Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Outdoor Dining Area
    • Terrace
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Tennis Court, Swimming Pool, Bocci, Soccer Lawn, Luxury Shelter Island 3-Bedroom<BR>Located in what is arguably the most desirable part of the island, this house appeals to guests who are looking for clean, modern, and stylish accomodations in a picturesque setting. Huge open kitchen with Sub-zero... View all property information
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    Shelter Island, Hamptons
    1 / 12
    Ocean Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Private Garden
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    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    NOW OFFERING A DISCOUNT OF $500 OFF PER WEEK FOR THE WEEKS OF 8/15, 22 AND 29!!! I pay the FLIPKEY fee--YOU DON'T!!! Fantastic Ocean Beach home. Prime location, by ocean. Half mile from ferry, restaurants and grocery. 1 block from Seaview. 2 Master bedrooms! 3 Full baths! Bi-level deck with... View all property information
    Location Information
    Ocean Beach, Fire Island
    1 / 16
    5 of 5 stars (8) Excellent
    East Hampton
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The house is really great for friends or families. It is very clean and modern with a bright open layout with an indoor/outdoor orientation. There are 3 bedrooms, each with a queen bed and 3 full baths. Two of the bedrooms have en-suite full baths. The 3rd bedroom has a full bath outside in the... View all property information
    Location Information
    East Hampton, Hamptons