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Holiday Rentals and Homes in Southampton, NY

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    Travellers to Southampton are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    1 / 9
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 bubbles (7) Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    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 / 23
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Located east of the canal on the beautiful Peconic Bay, over 100 feet of sandy beach, walk down the shore to for food, drinks and entertainment! Beautiful, crystal clear water, 5000 sq ft custom Waterfront “GREEN” House, 5 bedrooms, 5 baths , CAC, hardwood floors, in-ground heated pool, Outdoor... View all property information
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    Southampton, Hamptons 11946
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Southampton, Hamptons 11968
    1 / 27
    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
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    Southampton, Hamptons 11968
    1 / 50
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    If you're planning ahead for summer 2017, this is the time to ask me for a special deal. This open-plan house with second floor gallery and home theater in the basement brings the outdoors in. Wrap-around windows and skylights (plus an AC system with a stun button) gives you the best of the... View all property information
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    Southampton, Hamptons 11968
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
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    Southampton, Hamptons 11968
    1 / 28
    4 Bedrooms, 5 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Welcome to your private Hamptons escape! This immaculate Southampton vacation rental house is sure to provide the perfect vacation spot for your next family getaway. Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this gorgeous home is a terrific size and... View all property information
    Location Information
    Southampton, Hamptons 11968
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    1 / 6
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    4 Bedroom, 2 Bath House in Southampton<BR>Located on a Semi private lot south of the highway. Interior of the house has hardwood floors throughout and main living area has an open design with double high ceilings and large skylight. First floor living area includes 3 bedrooms, bathroom, kitchen... View all property information
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    Southampton, Hamptons 11968
    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 2 | Quick View
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    This private and quiet waterfront cottage is the perfect Hamptons retreat for one or two people. A short drive to the ocean beach or Main Street in the village for strolling and dining. Located near Southampton Village, the cottage is convenient for wine tasting excursions, antique hunting,... View all property information
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    Southampton, Hamptons 11968
    1 / 25
    5 of 5 bubbles (1) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    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 11968
    5 of 5 bubbles Reviewed 30 June 2015
    The house was very nice, clean and had everything we needed and more. The owners were very nice and accommodating. We were a group of 12 and were all very comfortable. We all...
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    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Enjoy the best of both worlds! Wake up and take your kayak or stand up paddle board across the street and out in the beautiful N. Sea Harbor & then head into nearby Southampton village for a nice relaxing lunch. Finish the day by soaking in the hot tub with a glass of wine & enjoying the... View all property information
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    Southampton, Hamptons 11968
    1 / 32
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Experience the exquisite relaxation of upper Long Island, New York by staying at this luxurious Southampton vacation rental home! With incredible upscale amenities, an alluring private pool, exclusive access to a pristine natural sand beach and close proximity to all the world-class attractions for... View all property information
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    Southampton, Hamptons 11968
    1 / 12
    4 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Porch
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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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    Southampton, Hamptons 06880
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Mint-renovated and newly decorated Southampton Village home offers a sunny living room, eat-in chef's kitchen and four bedrooms with two baths. Subzero and Wolf appliances, Waterworks fixtures, Cararra marble throughout. Enjoy the summer in our fully-fenced backyard sitting by the heated Gunite... View all property information
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    Southampton, Hamptons 11968
    1 / 12
    5 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Traditional 5 bedroom house on 1.5 acres south on Flying Point Road. Beautiful, mature gardens and heated pool. tons of living space and finished basement.Wood burning fireplace. large family room, library, double living room, two separate wings for sleeping and beautiful patio. gas barbecue.... View all property information
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    Southampton, Hamptons 11968
    1 / 13
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautifully gut renovated historic house in the heart of southampton village Be the first to stay in this beautifully renovated historic home. Gorgeous modern finished and decor. 3 bedroom with 3 ensuite bathrooms. and a 4th full bathroom on the main floor living space. This impeccably restored... View all property information
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    Southampton, Hamptons 11968
    1 / 11
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Fabulous Bay Front Villa on a private acre in Southampton close to village & Beaches. Beautiful fountain to greet you and your guests to the water front retreat with high end finishes. Vaulted ceilings, Professionally decorated and 6 Bedrooms with 4 1/2 baths with Jetted Tubs & Steam Shower. All... View all property information
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    Southampton, Hamptons 11968
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    1 / 16
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Newly Renovated Private Contemporary on 2 Acres of Privacy offers 5 Bedrooms 4 Bathrooms, Heated Pool, Hot Tub and All Weather Tennis Court. Bright and Airy lots of Glass & skylights with Glass doors to beautiful Bluestone patio perfect for Entertaining!<BR>Lush gardens with landscape lighting, i... View all property information
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    Southampton, Hamptons 11968
    1 / 9
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Price: $36,000 (June 15 to Labor Day) $17,000 (June) $18,000 (July) $29,000 (July through Labor Day) $20,000 (August through Labor Day) Neighborhood: Flanders Centrally Located West of Shinnecock Canal. Minimal traffic! Easy access to NYC and airports. Town of Southampton Lovely two-story Cape,... View all property information
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    Southampton, Hamptons 11901
    1 / 20
    7 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    About this property
    This two-story Southampton Traditional sits on nearly 3+/- acres and enjoys several magnificent amenities and attributes, including seven bedrooms and six and one half baths.There are both a formal/ informal dining area next to the eat-in kitchen. This two-story Southampton Traditional sits on... View all property information
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    Southampton, Hamptons 11968
    1 / 13
    4 Bedrooms, 10 Bathrooms, Sleeps 10 | Quick View
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    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 / 9
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Stunning Bay Front Stone Home with breathtaking views of the Bay, close to Southampton Village & Beaches. The Bay Front has 5 Bedrooms & 4 Bathrooms a Chefs Kitchen with views of the Bay. Vaulted Ceilings floor to ceiling Fireplace in Great Room. All Rooms have TV's and there is a 150 of Bulk... View all property information
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    Southampton, Hamptons 11968
    1 / 24
    4 Bedrooms, 10 Bathrooms, Sleeps 8 | Quick View
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    • Children's Pool
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    About this property
    Bishops Pond is a new high-end condo development in Southampton Village. The clubhouse offers a pool, fitness center, billiards, outdoor tennis court, and more. This beautiful and comfortable second floor level home located on the far south east corner of the development is exquisitely decorated,... View all property information
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    Southampton, Hamptons 11968
    1 / 9
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    About this property
    Fabulous newly renovated sprawling Contemporary with 2 acres of Privacy! All weather Tennis Court, heated Pool & hot Tub, open floor plan leads to a beautiful Blue Stone Patio perfect for entertaining. Walk to the Bay Beaches & close to the Village of Southampton. Beautiful New Kitchen with plant... View all property information
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    Southampton, Hamptons 11968
    1 / 7
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Spectacular view await you with this Charming Water Front Cottage a short distance from Southampton Village & Beaches! All the ammenities you need for a Summer to remember! Teak Furnishings for your out door dining Al Fresco & a heated unite pool for comfortable swimming. Vistas of water & Wildlife... View all property information
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    Southampton, Hamptons 11968
    1 / 7
    5 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
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    About this property
    You can rent this weekly, bi-weekly or full summer season. Summer 2015 weekly rentals start at $7000/week for any weeks in June, $8750/week for any weeks in July and $9200/week for any weeks in August. You can rent for as little as a week in the summer season or monthly or seasonal. In the... View all property information
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    Southampton, Hamptons 11968
    1 / 19
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    About this property
    The quintessential Infamous Hamptons showcases the posh, yet understated style characteristic to this legendary holiday destination. In an area of New York renown for its five star restaurants and VIP night clubs, there’s actually more to a holiday in Southampton than all the glitz and celebrity.... View all property information
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    Southampton, Hamptons 11968
    1 / 18
    4 Bedrooms, 11 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    THIS SOUTHAMPTON HOME OFFERS PRIVACY, LUXURY ,SERENITY AND IS EXQUISITELY DECORATED ,THIS RENTAL HAS EVERYTHING ONE WOULD ASK FOR AS THE OWNER.I LIVE THERE PART TIME AS WELL AND HAVE GIVEN THE UTMOST ATTENTION TO EVERY DETAIL IN THE HOUSE FOR ONES COMFORTS<BR>THIS HOUSE HAS 4 BEDROOM TWO OF WHICH... View all property information
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    Southampton, Hamptons 11968
    1 / 24
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Escape to the prestigious Hamptons and book your stay in this truly magnificent 4-bedroom, 5.5-bathroom Southampton vacation rental house, which sleeps 8! This wonderful New York property features stunning amenities and a desirable location to help make your luxurious getaway all the more... View all property information
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    Southampton, Hamptons 11968
    1 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Step inside this stylish, recently renovated 3 bedroom, 3 bath Southampton home, and the stage is set for a perfect Hamptons summer vacation. Gorgeously appointed and sun-lit, the open floor plan encompasses a great room with fireplace, a screened three-season dining area, a stunning kitchen with... View all property information
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    Southampton, Hamptons 11968
    1 / 29
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Enjoy the summer at 147 Warfield Way, part of the Southampton Shores community offering a private community bay beach, marina, 3 tennis courts and playing fields. Convenience couldn't be easier with the Country Deli close by as well. Built by Farrell Building in 2014 this house and property has it... View all property information
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    Southampton, Hamptons 11968
    1 / 21
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Large open 2 story unit with all brand new appliances and brand new furniture throughout the condo with a brand new 60" flat screen TV. The condo comes with an extra large master bedroom, and beautiful walk in closet and a nice size master bathroom. The second bedroom comes with a beautiful full... View all property information
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    Southampton, Hamptons 11968
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Charming 3 bedroom Hampton's beach cottage, with cable and wifi available,private patio and garden. 3 minute walk to beautiful ocean beach, gas grill on patio, outdoor shower, fully equipped, kitchen with dishwasher, and all utensils. washer and dryer, all bed linens and towels, beach chairs and... View all property information
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    Southampton, Hamptons 11962
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The house Sleeps 6! The home has 3 bedrooms, Bedrooms 2 King 2 twin Like a 4-star hotel, quality linens and towels are provided. We also have 4 other Southampton homes located near by if your needing more accommodations. You'll be a mere 3 miles away from the ocean beaches of Southampton AND... View all property information
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    Southampton, Hamptons 11968
    1 / 28
    4 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    This home is perfectly located in Southampton. It is a 4 Bedroom, sleeps 10. If you have been wanting to visit The Hampton's for the first time house is the perfect choice since its perfectly located in the heart of the Hampton's, just a three minute drive to the village with all the wonderful... View all property information
    Location Information
    Southampton, Hamptons 11968
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Terrace
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Newly updated 4 bedroom 2 bathroom house in Sag Harbor ! Stroll to town, restaurants, shops, cafés, Washer/dryer, central heat/AC, wrap around deck, outdoor gas grill, new appliances, 2 queen beds 2 twin beds, high end linens towels ect, plenty of cooking/kitchen utensils, flat screen cable tv,... View all property information
    Location Information
    Southampton, Hamptons 11968
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 with hot tub. The home is clean, stylishly decorated, and steps away from a gorgeous nature preserve. Getaway now and visit Southampton town only 3... View all property information
    Location Information
    Southampton, Hamptons 11968
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The house is located just a few blocks from the Village of Southampton and a few blocks from the most beautiful beaches in the world. It is in one of the most desirable neighborhoods in Southampton. We also have 4 other Southampton homes located near by if your needing more accommodations. The... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 37
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Hot Tub
    • DVD Player
    • Private Outdoor...
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    If you have been wanting to visit The Hampton's for the first time this house is the perfect choice since its perfectly located in the heart of the Hampton's, just a three minute drive to the village with all the wonderful restaurants, clubs and small shops. the beach is just as close. There is... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 31
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Every season is beautiful here, so relax and get away from it all. Situated at the gateway to the Hamptons, the Easterner Motel is located in charming, bucolic Shinnecock Hills, just five miles from Southampton Village and the famous, stunning beaches of Southampton, and beyond, all the way to the... View all property information
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    Southampton, Hamptons 11968
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    About this property
    Don't be surprised if you wake in the morning to see a deer or two outside your window as you make your way to the sunroom. This charming, 2 bedroom plus bonus room, 2 full bath and outdoor shower boasts a newly renovated kitchen with high-end appliances, Central Air-Conditioning, newly, refinished... View all property information
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    Southampton, Hamptons
    1 / 7
    6 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Hot Tub
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    • Satellite TV
    • Waterfront
    • Sauna
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    waterfront villa estate with;everything!!!!! Beds: 3 King Beds, 2 Queen Beds, 1 Double Bed, 2 Sofa Beds, 1 Crib View all property information
    Location Information
    Southampton, Hamptons 11959
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Air Conditioning
    • Ocean Views
    • Sauna
    • Waterfront
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    • Wi-Fi
    • Private Indoor Pool
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Custom Estate on the bay for relaxation, boating and sailing from premises, one mile from world class ocean beach, restaurants, railroad into New York City. We are west of the Shinnecock Canal away from the traffic in private neighborhood on private sandy road. Includes 50 foot heated indoor pool,... View all property information
    Location Information
    Southampton, Hamptons 11946
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    • Hot Tub
    • DVD Player
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    • Private Outdoor...
    • Satellite TV
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    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This one has it all! On two acres of private land, boasting 6,500 square-feet of beautiful and elegant interior spaces, decorated by a noted interior designer. There are six en-suite bedrooms (master bedroom pictured), five and one-half baths, a heated oversized 20' x 50' Gunite pool with adjacent... View all property information
    Location Information
    Southampton, Hamptons