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Homes in Long Island, NY

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    343 Holiday Rentals in Long Island
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    $1,010
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    1 / 23
    5 of 5 stars (2) Excellent
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    $6,435
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    5 of 5 stars (1) Excellent
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    4.5 of 5 stars (3) Very good
    Overview Reviews (3)
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    About this property
    Our Quaint two bedroom house offers easy access to everything on Shelter Island. Large backyard offers room to kick back or to run around. Bedrooms are comfortable. one with a queen size bed, another with two twins - for those kids of yours, or push them together for a king size bed for extra... View all property information
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    Shelter Island, Hamptons 11964
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    $386
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    1 / 19
    5 of 5 stars (4) Excellent
    Overview Reviews (4)
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    About this property
    Welcome to Fire Island Pines Retreat. We are a gay guesthouse on Fire Island Pines, a gay community off the coast of Long Island. We pride ourselves on offering extremely comfortable accommodations at reasonable prices, and look forward to welcoming you to Fire Island Pines. Our home is very... View all property information
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    About this property
    Be one of the first to rent this newly gut renovated 3 bedroom 2 bath home situated in a private community within 4 minutes of downtown Bridgehampton and 5 minutes to Sag Harbor Village. You could not ask for a better location when visiting the Hamptons. The home has beautiful light and is bright... View all property information
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    Location Information
    Bridgehampton, Hamptons 11932
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    $1,544
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    About this property
    8 bedrooms, 8 baths (6 full, 2 half); sleeps 16. Rock-star type oceanfront house in West Hampton Beach (Dunes), LI., with endless luxury amenities. 2007 construction, 5000 square feet, on nearly 90 feet of oceanfront on prestigious Dune Road (the 600 block, closer to the bridge / town). More... View all property information
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    Westhampton Beach, Long Island 11978
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    $1,609
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    About this property
    25 year age limit...please don't inquire if you do not meet the age requirements, you will be wasting your time and ours. This estate has 7 bedrooms and 6.5 bathrooms, all bathrooms are marble with high-end fixtures. All bedrooms have 32 inch HDTV's. Boasting 2 living rooms - 1 on the main floor... View all property information
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    Location Information
    Southampton, Hamptons 11968
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    $322
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    1 / 16
    4.5 of 5 stars (5) Very good
    Overview Reviews (5)
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    About this property
    Just outside East Hampton Village, the Hamptons Brazil Guest House is a charming Bed & Breakfast, a cozy cottage owned and maintained by native Brazilian and long-time Hamptons resident Heloisa Brandao. A renowned Interior Designer, established artist, Heloisa provides guests with an attractive... View all property information
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    $643
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    Overview Reviews (6)
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    • Suitable for children
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    About this property
    Located in Southampton's largest natural area - Big Fresh Pond. Treat yourself with abundance of nature, tranquility and available activities! 8000 sqft total of private space including 4000 sqft of private peaceful lakefront with dock and kayaks, 2000 sqft of indoor space and 2000 sqft of private... View all property information
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    Location Information
    Southampton, Hamptons 11968
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    $1,544
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    Overview Reviews (2)
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    About this property
    Location, location, location! In its ideal location on a charming, quaint cul de sac in beautiful East Hampton Village, this brand new 4-5 bedroom, 4½ bath vacation home has it all. Luxury, luxury, luxury! Its amenities include a heated swimming pool, central air-conditioning, a charming covered... View all property information
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    $836
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    1 / 12
    4 of 5 stars (1) Very good
    Overview Reviews (1)
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    About this property
    The all white interior of this 3 bedroom, 2 bath contemporary features stunning decor, a bright, light environment and vaulted ceilings with skylights. Living up to its name, the Contemporary has just undergone a complete state-of-the-art renovation prior to the 2010 season. It now boasts an... View all property information
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    Peconic
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Waterfront
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    About this property
    Enter a world of tranquility and surround yourself with the beauty of nature! 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 remodeled... View all property information
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    Location Information
    Peconic, North Fork 11958
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    $643
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    Overview Reviews (7)
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    • Dishwasher
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Located in Southampton's largest natural area - Big Fresh Pond. Treat yourself with abundance of nature, tranquility and available activities! 8000 sqft total of private space including 4000 sqft of private peaceful lakefront with dock and kayaks, 2000 sqft of indoor space and 2000 sqft of private... View all property information
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    Location Information
    Southampton, Hamptons 11968
    From
    $225
    / Night
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    Overview Reviews (5)
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    • Air Conditioning
    • Balcony
    • Fireplace
    • Grill
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    • Private Fishing...
    • Satellite TV
    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Wheelchair access
    • Elder access
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    About this property
    1 Br Beach Cottage Sleeps 4, 1Full bath, Fully equipped kitchen w/Appliances Brand new affordable beach cottage guest house, located directly on the beach! This stunning 1 Br beach guest house is magnificently located right on the beach, with a large patio/deck with a large BQ lounge chairs and... View all property information
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    Location Information
    Wading River, Long Island 11792
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    $225
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    Overview Reviews (3)
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    • Smoking allowed
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    About this property
    THIS CHARMING, “LITTLE BIT OF OLD WORLD” 2/3 BEDROOM VINTAGE COTTAGE IS SITUATED ON THE THE PINNACLE OF A CLIFF OVERLOOKING THE BEAUTIFUL LONG ISLAND SOUND! THIS HOME IS FULLY FURNISHED WITH A WELL EQUIPPED KITCHEN, A LARGE LIVING ROOM WITH A DINING AREA, ATTRACTIVE ANTIQUES AND VERY INTERESTING... View all property information
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    Location Information
    Wading River, Long Island 11792
    From
    $901
    / Night
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    Overview Reviews (4)
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    • Smoking allowed
    • Suitable for children
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    About this property
    This 6 Bedroom luxury Beach House is located directly on the beach. This home is a perfect location for bachelorette parties, family reunions, and couple's retreats. You can visit the great Long Island wineries, golf . This luxurious 6 Bedroom beach house is among our most desirable homes. This... View all property information
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    Location Information
    Wading River, Long Island 11792
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    $129
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    • Water Views
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    • x
    • x
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    About this property
    Charming cottage in the woods just steps from the peaceful Long Island Sound. This cottage has two bedrooms and sleeps 6. Built in 1950, this cottage has been passed though two generations. Owned by one of the original families who started it all. This community was once camping / tent grounds... View all property information
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    Location Information
    Baiting Hollow, Long Island 11933
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    $515
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    1 / 30
    5 of 5 stars (2) Excellent
    Overview Reviews (2)
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Fireplace
    • Gym
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    • Private Fishing...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
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    About this property
    This home was just rebuilt this summer. This house is beautifully decorated with fine furniture, 2 bedrooms with queen size beds and bathroom. The other bedroom has 2 full beds. When you leave the bedrooms and enter into the great room, there are windows all around looking out to the water and your... View all property information
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    Location Information
    Wading River, Long Island 11792
    From
    $772
    / Night
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    Overview Reviews (2)
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Spectacularly furnished luxurious 5 bedroom Beach House on the beach. This high end one of a kind home has everything you need for a holiday to remember. Perfect home for a family reunion or get together or a bachelorette or all girl weekend getaway or couples retreat. Come and visit this beach... View all property information
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    Location Information
    Wading River, Long Island 11792
    From
    $386
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    Overview Reviews (5)
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    • Air Conditioning
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    • Dryer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This 4 bedroom beach house sleeps 10 (we also have a guest house available across the way, that can sleep 4 more, please inquire) This beach house is available year round and has a 3 tier deck where you can enjoy panoramic views of the Long Island Sound. You can even have a lobster bake or Catering... View all property information
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    Location Information
    Wading River, Long Island 11792
    From
    $1,094
    / Night
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    Overview Reviews (4)
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    About this property
    This striking custom-built Cape Cod design offers space and luxury in a pristine, immaculate vacation home. Virtually new, it features 4 expansive, luxurious bedrooms, 3 1/2 beautifully tiled baths, a designer kitchen with Corian counter tops, state-of-the-art appliances, Mexican tile, and wide oak... View all property information
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    $515
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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 swim in our heated pool by day. Oversized modern... View all property information
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    Location Information
    Cherry Grove, Fire Island 11742
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    $643
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    3 of 5 stars (1) Average
    Orient
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Pets allowed
    • Smoking allowed
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    • x
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    About this property
    Pernchief Cottage Located In The Village Of Orient Is The Perfect Place To Summer With Family And Friends. Front Porch Offers Lovely Views Of The Bay. Wide Pine Floorboards, Great Architectural Detils Abound. Property Is Beautifully Set On 1/2 Acre With Lovely Gardens And A Tranquil Pond. Charming... View all property information
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    Orient, North Fork 11957
    From
    $322
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    Overview Reviews (1)
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    • Dishwasher
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    • Suitable for children
    • ?
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    • x
    About this property
    This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away... View all property information
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    $32,173
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    1 / 9
    1 of 5 stars (1) Terrible
    Overview Reviews (1)
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    • Grill
    • Hot Tub
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    • Pets allowed
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    About this property
    Beautiful house, 8 bedrooms 7 bathrooms, beautiful residential area. pool, hot tub, Tennis Court, basketball, beach Volley Ball court, C/A/C, whireless Internet connection, BBQ and much more. about 4-5 miles to the beach, winerries, cafes and galleries. View all property information
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    Location Information
    East Quogue, Hamptons 11942
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    $10,810
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    Westhampton
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Classic historic colonial with five bedrooms and five en suite bathrooms (five full bathrooms, one powder room, one outdoor shower), on mature lush grounds south of the Montauk Highway, close to the water in Westhampton. The heated gunite SALT WATER POOL is very kind to the skin and eyes of the... View all property information
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    $611
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    • Air Conditioning
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    • Pets allowed
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    About this property
    Southampton Designer's Escape The Space Lots of large windows and glass doors make this home bright and warm all year long. Art adorned walls and colorful original textile designs by the artist/designer are throughout. The layout is great for entertaining and relaxing. Both open and private,... View all property information
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    Location Information
    Southampton, Hamptons 11968
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    $425
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    Southampton
    4 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Pets allowed
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    About this property
    Charming century-old wood-frame and shingled cottage located in a former artists' colony in Southampton, NY, close to beaches, shopping and sight-seeing. Has been well-maintained and steadily upgraded to respond to modern expectations. Tenants may bring a dog. I am looking for seasonal or monthly... View all property information
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    Location Information
    Southampton, Hamptons 06880
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    $643
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    • Pets allowed
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    About this property
    This impeccable 5 bedroom/3.5 bath home is located in a private bay community on a beautifully landscaped 1 acre south of the highway. It is a short walk from private bay beach and a 5 minutes drive from the ocean beaches. Renovated in 2011 and tastefully decorated in a contemporary, comfortable... View all property information
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    Location Information
    East Quogue, Hamptons 11942
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    East Quogue
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Charming, Pottery Barn type home close to Ocean and bay in the Hamptons! This is a charming 3 bedroom two bathroom ranch in the heart of E. Quogue. It is ideal for a couple or small family. It is set up with many beautiful details and flower gardens. Not a typical share house or “rental house”... View all property information
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    East Quogue, Hamptons 11942
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    $322
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    • x
    About this property
    Monthly Rates: July-August: $3,000 per month September: $2,500 per month October-June: $1,800 per month Daily Rates: July – August: $325/night weekdays $425/night weekends September: $295/night weekdays $399/night weekends October –June: $225/night weekdays $300/night weekends (50%... View all property information
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    About this property
    Spacious East Hampton vacation home features four large, furnished bedrooms with oversized master and walk-in closet, three full bathrooms with modern hotel finishes, large custom kitchen with stainless steel and paneled appliances, sunny family/living room with working fireplace, wireless... View all property information
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    $2,831
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    About this property
    Sweeping views of th Great South Bay from this 2 BR, 1-1/2 bath gem. Get your friends and your beach towels an think BEACH right now! View all property information
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    Location Information
    Cherry Grove, Fire Island 11782
    From
    $637
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    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
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    Fair Harbor
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Safe
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    • Suitable for children
    • ?
    • x
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    An ideal spot for a comfortable, peaceful beach vacation. Our charming, newly 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... View all property information
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    Fair Harbor, Fire Island 11706
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    Greenport
    4 Bedrooms, 9 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Balcony
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    • Pets allowed
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    • x
    • x
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    A gem of a getaway! There are four bedrooms, of which three are located upstairs. Two of the upstairs bedrooms share one new en-suite bathroom. One bedroom upstairs has it's own en-suite bathroom. The bedroom on the ground floor has an en-suite water closet and another full bathroom. The cottage... View all property information
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    Greenport, North Fork 11944
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    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    The Space The Old Schoolhouse tells a family story, dating back to the 1880's. This charming farmhouse, built by the Burt family in the 1880's, was first used as a schoolhouse, then transformed into a farmhouse. The Burt family updated the house in 2005 with the most energy efficient systems, so... View all property information
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    Greenport, North Fork 11944
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    Overview
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    • Air Conditioning
    • Balcony
    • Dishwasher
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    • Gym
    • Hot Tub
    • Internet Access
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    • Suitable for children
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    • x
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    About this property
    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
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    Baldwin, Long Island 11510
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    Post modern traditional farm house set on over an acre on quite Picturesque cul-de-sac walking distance to great bay beaches, boat launches, Parks, Marinas and restaurants. Five minute ride to village and ocean beaches. House has four bedrooms, three full baths, formal dinning room, library/office... View all property information
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    Overview
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    • Air Conditioning
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    • Hot Tub
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    • Private Outdoor...
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    6 bedroom, 4 bathroom Contemporary. Open floor plan, soaring ceilings; brand new kitchen and dining area. Pool, outdoor shower, hot tub. 5 minutes to beach, village, 7 minutes to Sag Harbor Village. Also available for holidays and special occasions short term. View all property information
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    Hampton Bays
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Fireplace
    • Gym
    • Hot Tub
    • Internet Access
    • Pool Table
    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Immaculate four bedrooms, three full baths sleeps 8-10. Full gym, pool and jacuzzi nestled away in prestigious Red Cedar Ridge. Wi-fi internet and premium channels cable tv. Pool table, basketball and children play ground for entertainment. Five min drive to bay beach, fifteen min to ocean beach... View all property information
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    Hampton Bays, Hamptons 11946
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    $642
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    Overview
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Stunning views, master suite, deck, sunrooms, private lane and beaches Completely renovated and enlarged to double the footprint this winter with new kitchen, two and a half new bathrooms with tubs and showers and large master bedroom suite overlooking the Ashamomaque inlet in Southold, with... View all property information
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    Hamptons
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    This is a gorgeous newly renovated hamptons shingled farm style home. 4 bedrooms 4 full bathrooms huge kitchen for entertainers, dining room & living rooms Pool, fireplace, deck for entertaining, lots of space and plenty of natural lighting. Brand new furniture and top of the line appliances.... View all property information
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    Southampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
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    About this property
    A very private and charming getaway minutes from the the ocean, the bay, and Southampton Village shopping and activities. Also centrally located to the other Hamptons villages and a ferry ride away to Shelter Island and the North Fork, our home is the perfect base from which to explore the beauty... View all property information
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    Southampton, Hamptons 11968
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    Southampton
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Shared Outdoor Pool...
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    • x
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    About this property
    Farmhouse style house in the Village of Southampton within walking distance to train station, railway station, downtown, and bicycle to the beach. House has 2 1/2 bedrooms, 2 1/2 baths, heated swimming pool. NO GROUP Rentals single family only!!!!!!!!!! House only available for a monthly rental... View all property information
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    Southampton, Hamptons 11968
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    $5,148
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    Southampton, Luxury 4 Bed 2 Bath home with pool, minutes to everything! New 25 x 50 Salt Generated Pool, no maintenance and much easier on the eyes! 3 Minutes to Private Beach! Free Parking, NO Beach Passes needed! This 4 bedroom, 2 bath home is nestled on 1.5 acres which abuts a 10 acre... View all property information
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    Southampton, Hamptons 11968
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    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
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    Location Information
    Westhampton Beach, Long Island 11978