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Long Island Holiday Rentals

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    Travellers to Long Island are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 10
    Sag Harbor
    1 Bedroom, 1 Bathroom, Sleeps 8 | Quick View
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    1 / 22
    Bridgehampton
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    1 / 33
    Valley Stream
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 12
    Montauk
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This Is a smartly furnished, relaxing house close to everything that beautiful Montauk has to offer. We just purchased the house In April 2015 and did an extensive renovation... new bathrooms, new floors, new A/C, painted, and new appliances. The house Is warm and relaxing and is drenched in... View all property information
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    Montauk, Hamptons 11954
    1 / 19
    Shelter Island
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    About this property
    "1 Master bedroom with King size bed and another bedroom with 2 Queen size beds. Sleeps 6. Newly renovated with top of the line furniture, this house is close to: world renown Sunset Beach restaurant by famed owner Andre Balazs, Commander Cody's, Marie Eiffel Dockside Market, Mashomack Preserve,... View all property information
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    Shelter Island, Hamptons 11964
    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 11960
    1 / 11
    East Hampton
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    East Hampton ,NY 3 bedroom 3 bath house with pool cabana, Near Ocean beaches -3 miles-2 1/2 miles to the village/town.Home is fully loaded with wifi,cable(4 cable boxes and flat screen tvs and nice cable package). Wood floors and ceiling fans throughout the house,a/c, finished basement with... View all property information
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    East Hampton, Hamptons 11937
    1 / 13
    East Hampton
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This lovely home includes a chefs kitchen, formal dining, spacious living area and 1st floor Master suite.There is also a finished lower level with a recreation room, gym, with an additional two bedrooms and a bathroom. Exterior includes two car garage, heated pool with water feature and spa. Just... View all property information
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    East Hampton, Hamptons 11937
    1 / 9
    Southampton
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    This spacious 5 bedroom, 5.5 bath home provides an amazing living room with vaulted ceilings and 2 wood burning fireplaces. Expansive windows and French Doors overlook the landscaped grounds and heated gunite pool. Top-of-the-line appliances in the kitchen with granite countertops, desk, wine... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 23
    5 of 5 bubbles (9) Excellent
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Porch
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    • Pet-friendly
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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 11971
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    1 / 13
    Springs
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    This one level contemporary is located on a private, beautifully landscaped and wooded lot bordered by a nature preserve in an upscale neighborhood in the Springs section of East Hampton. For the past 16 summers, guests have raved about this home. It is tastefully furnished and has a spacious,... View all property information
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    Springs, Long Island 11937
    1 / 8
    Sag Harbor
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • x
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    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
    1 / 21
    5 of 5 bubbles (2) Excellent
    Bridgehampton
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Bridgehampton White House RATES INCLUDE THE FOLLOWING: Electric consumption, cable TV & wi-fi, propane consumption, telephone, trash removal, lawn & pool service and heating of pool to 85 degrees between Memorial Day and Labor Day. OVERVIEW OF HOME: 3 bedrooms 3 bathrooms Finished Basement with TV... View all property information
    Location Information
    Bridgehampton, Hamptons 11932
    1 / 9
    Sagaponack
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Outdoor Pool...
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    • x
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    About this property
    600 Sqft, Cottage on Sagaponack Lake in beautiful private estate setting and is ideal for short term stays. This studio features a an open living area with a fireplace. There is no stove, but a microwave and toaster oven is provided. Full access to pool and grounds. Owner will not be in residence... View all property information
    Location Information
    Sagaponack, Hamptons 11962
    1 / 37
    5 of 5 bubbles (7) Excellent
    Aquebogue
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Five bedroom home with central air conditioning.This home has modern kitchen pillow top bed a large 52" plasma tvs.This home has tv in master and queen br bbq grill,12 gazebo with a tumbled stone patio.The patio has a table with seating for eight The view from the gazebo area is about one mile... View all property information
    Location Information
    Aquebogue, Riverhead 11931
    1 / 27
    Southampton
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • x
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    • x
    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 11968
    1 / 24
    Southold
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • x
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    • x
    About this property
    Large beach front with 5 bedrooms (2 ensuite), 4 living rooms, 3.5 baths This is the perfect home for the extended family vacation, with not only 5 bedrooms, including 2 with ensuite bathrooms but 4 separate sitting/family/den or game rooms plus a pool room! The unique layout offers areas to gather... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 15
    East Quogue
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Light, Bright And Completely Renovated. Spacious Modern Contemporary Home. Offers 5 Bedrooms, 3.5 Baths On Over 2 Private Acres. Enjoy Heated Pool, Hot Tub And Tennis, Foosball And Ping Pong. Great Room W/Fireplace And Wall Of French Doors. Open To Expansive Poolside Deck Inviting Outdoor... View all property information
    Location Information
    East Quogue, Hamptons 11942
    1 / 30
    Southampton
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
    About this property
    Be close to everything the Hamptons has to offer while getting away from it all in your little piece of paradise.! You'll be a mere 1 mile away from the ocean beaches of and in close proximity to the Hampton Village of Southampton - with its exciting selection of restaurants, shops, movie theater,... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 18
    Bellport
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    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... View all property information
    Location Information
    Bellport, Long Island 11713
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    1 / 17
    Bridgehampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Enjoy this 4 Bedroom, 2.5 Bath Post Modern Home with Screened in Porch and Heated Pool. Conveniently Located between Sag Harbor and Bridgehampton, Beautifully and comfortably decorated, a few minutes to restaurants and the beaches! This is the best location you can get with lots of rooms to relax... View all property information
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    Bridgehampton, Hamptons 11932
    1 / 24
    Southampton
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This 3 bedroom waterfront cottage is a perfect family getaway. Located in a small beach community between Southampton and Sag Harbor, it is surrounded by water - from the dining room you look right out onto a serene lake, from the first floor you can see both lake and the bay beach. You are only a... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 26
    Westhampton Beach
    2 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • Ocean Views
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    • x
    • ?
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    • x
    About this property
    2 beds 4 baths 1,600 SqFt West Hampton Beach House: Lauren Berger Collection presents a magical dream vacation home on the West Hampton Beach. A Spectacular new construction, newly decorated 2 Bedroom 4 Bathroom home direct on the beach. This is a rare opportunity to spend your vacation in this... View all property information
    Location Information
    Westhampton Beach, Long Island 11978
    1 / 12
    East Setauket
    5 Bedrooms, 8 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
    • Ocean Views
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    • x
    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 11733
    1 / 18
    Southold
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
    • Ocean Views
    • Porch
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    • Pet-friendly
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    • ?
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    • ?
    About this property
    Escape to this idyllic beachfront located directly on the Sound in Southold NY, only 1 hour 45 minutes from NYC. Open-air, camp-style rooms are part of the house's simple charm. Linger over meals with family and friends on the screened-in porch, watch mesmerizing sunsets, swim in the salt water,... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 16
    Greenport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
    • x
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    • x
    About this property
    Walking distance to Greenport Village, Sound and Bay Beaches! 1200 sq ft Victorian cottage perfect for a retreat from the heat. Large patio, new kitchen and bath! 1840s historic poet's house, perfect for couples, small family or single seeking reprieve from Manhattan. Original hardwood floors, 2... View all property information
    Location Information
    Greenport, North Fork 11944
    1 / 16
    Montauk
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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
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    Montauk, Hamptons 11954
    1 / 27
    Sag Harbor
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • x
    About this property
    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 & Jacuzzi. The home is clean, stylishly decorated, and steps away from a gorgeous north Sea bay beach. Visit Southampton or Sag Harbor town only 3 min... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 15
    Amagansett
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Beach house right on the sand, just a block away from a beautiful, uncrowded Atlantic Ocean beach. Clean and comfortable. Upstairs deck and downstairs patio off eat-in kitchen. Big living room, three bedrooms, two full bathrooms, washer and dryer, outdoor shower, gas grill, cable TV, internet... View all property information
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    Amagansett, Hamptons 11930
    1 / 11
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • 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 / 13
    Mattituck
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • x
    • ?
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    • x
    About this property
    The Space The New York TImes Real Estate Section on Sunday, Feb. 9th, 2014, talked about the multi-million dollar homes being built in the Hamptons. The article said, "The look of the homes is evolving: modern is making a comeback, but modern in the guise of barnlike. 'The modern barn is the... View all property information
    Location Information
    Mattituck, North Fork 11952
    1 / 22
    5 of 5 bubbles (4) Excellent
    East Hampton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    This immaculate NW Woods Ralph Lauren furnished modern contemporary home has it all including a Hot Springs Spa, custom Heated Pool with stand alone Pool House, 3000 sq. ft. of decking that wraps around entire back of home leading down to the pool area with all the outdoor furniture/seating you... View all property information
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    East Hampton, Hamptons 11937
    1 / 12
    Montauk
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    About this property
    Wonderfully relaxing home with view of the Atlantic Ocean and morning sunrise.Our home is walking distance to town and the beach.Gentle afternoon breezes surround you as you relax with a glass of wine, barbecuing your dinner on the outside deck ,contemplating the day you just spent at the... View all property information
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    Montauk, Hamptons 11954
    1 / 6
    Sag Harbor
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    This beach vibes cottage is located in Sag Harbor village, you can walk to town, bike or walk to the beach. The house is located in the only private beach community in Sag Harbor. The cottage comes fully furnished with everything you need to have a memorable stay in Sag Harbor. No smoking Not... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 9
    4 of 5 bubbles (1) Very good
    Jamesport
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Spend a relaxing few days at our romantic vineyard and winery in our newly finished 650 sq. ft. luxury apartment situated on beautiful Manor Lane in Jamesport. Our one bedroom (queen size bed), bath w/shower, large open living room, kitchenette, cathedral ceiling, flat screen TV, Cable, WiFi,... View all property information
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    Jamesport, North Fork 11947
    1 / 13
    Sagaponack
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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
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    Sagaponack, Hamptons 11962
    1 / 10
    East Hampton
    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
    Our new house is on a very quiet street on an elevated site in the woods. We are located halfway between East Hampton and Sag harbor. The Sag harbor golf course is just around the corner where you can play golf or catch the great sunsets. Beaches are all very close. Wainscott and main beach are a... View all property information
    Location Information
    East Hampton, Hamptons 11937
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    East Hampton
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Located down a winding drive in the town of East Hampton our four bedroom home was constructed in the classic Hampton's style with cedar shingles and white wood trim. Sited on an acre and a half in the Northwest Woods, beautifully landscaped and private with close to 20 acres of reserve land... View all property information
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    East Hampton, Hamptons 11937
    1 / 30
    5 of 5 bubbles (1) Excellent
    Hampton Bays
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    For family or group adults over 28 years old please up to max.8 guests inquire with your specific details for availability I'm on several sites.Not a party house.quiet relaxing time outdoors especially 10pm and 11pm on holiday. Min.2 nights JUN or SEP, 3 nights JUL5-SEP4, 4 nights for... View all property information
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    Hampton Bays, Hamptons 11946
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    Wainscott
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Enjoy this Charming Renovated Cottage with 2 Bedrooms, 1 Bath, Beamed Vaulted Ceilings and a Screened in Front Porch. A pretty kitchen is located in one end of the house that leads to the pool with waterfall. The Master bedroom is located on the first floor with a very large walk in closet. With... View all property information
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    Wainscott, Hamptons 11975
    1 / 55
    5 of 5 bubbles (7) Excellent
    Southampton
    7 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    • Wi-Fi
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    • Waterfront
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
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    Southampton, Hamptons 11968
    1 / 15
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
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    East Hampton, Hamptons 11937
    1 / 24
    Westhampton Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Private Garden
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Brand New home finished in January 2016. Walk to Main Street (Walking distance to synagogue) , Mile and half from beaches, mile away from Quogue Wildlife Refuge or stay home with heated pool. Features 4 full Bedrooms with Bonus room that can be used as separate bedroom. Bedrooms upstairs - 1... View all property information
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    Westhampton Beach, Long Island 11978
    1 / 13
    Southampton
    4 Bedrooms, 10 Bathrooms, Sleeps 10 | Quick View
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    • Parking
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    • Ocean Views
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Getaway to this charming Cottage on the water with spectacular views!! 3 Bedrooms & Baths in the main house with a separate<BR>guest cottage with Bedroom, Kitchen & Bathroom. Heated water front Gunite Pool, Hot Tub, Dock plus Kayaks & Bikes. Close to the village of Southampton, beaches and all the... View all property information
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    Southampton, Hamptons 11968
    1 / 18
    Sag Harbor
    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
    The feeling of Zen surrounds you as you enter upon this European designer's hideaway..Custom appointments of quality and luxury fill this Hampton's home. Located 12 minutes walk to Main Street of the prestigious Sag Harbor Village....0.4 acres of beautifully manicured totally private lawns with... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 10
    Springs
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
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    Spend this summer vacationing in the Hamptons at this East Hampton 3 bedroom, 2.5 bath home. This spacious home is great for entertaining, its also a close... View all property information
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    Springs, Long Island 11937
    1 / 24
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Garden
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Escape to the scenic seaside village of Greenport in this 2-bedroom, 2-bathroom vacation rental apartment that comfortably sleeps 4. Located in the heart of Greenport Village, enjoy quick access to fine restaurants, exceptional shopping and numerous local attractions. Boasting 1,850 square-feet of... View all property information
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    Greenport, North Fork 11944
    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
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    Bellport, Long Island 11951
    1 / 16
    Baiting Hollow
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Seasonal rental within a 5 minute walk to private beach, ten minute walk to Giorgio's. 5 minute drive to local horse riding farm and ten minutes drive to local north fork wineries. 10 minute drive to downtown Riverhead, Long Island rail road, outlets and restaurants.... View all property information
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    Baiting Hollow, Long Island 11933
    1 / 17
    East Hampton
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Satellite TV
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    • Wi-Fi
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    • Secure Parking
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our beautiful four bedroom, two bathroom beach house is newly renovated and available for rent! Located on .7 acres, this property is a dream come true for all those looking for a peaceful escape into one of the most beautiful parts of the country. Our lovely home is located only 7 minutes away... View all property information
    Location Information
    East Hampton, Hamptons 11937