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Holiday Rentals nearby Stony Brook Southampton

239 Montauk Hwy, Southampton, New York 11968
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    Travellers to Southampton are booking May dates now. Secure your holiday home today, and have the perfect trip.
    All 26 Rentals in Southampton
    Hampton Bays, south of 27A1 / 27
    (14)Excellent
    1.5 kilometres from Stony Brook Southampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Quaint Seaside Retreat With Full Gym1 / 71
    (5)Excellent
    3.9 kilometres from Stony Brook Southampton
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Luxury Hampton Bays Home - Walk to Shinnecock Bay1 / 25
    (1)Excellent
    3.4 kilometres from Stony Brook Southampton
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Lavish Southampton House w/ Private Beach & Pool!1 / 32
    (2)Excellent
    3.9 kilometres from Stony Brook Southampton
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    My husband and I stayed here over the fall for the long weekend. The house and décor were truly beautify, exactly what you’d think of for Hamptons style. It had big bay windows...
    Reviewed 22 May 2017
    Came here for a couples getaway with my wife and some friends. Had a great time and ended up inviting some friends from CT to join us when we realized the house sleeps many more...
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    About this property
    Experience the exquisite relaxation of upper Long Island, New York by staying at this luxurious and expansive 4-bedroom, 4-bathroom vacation rental in Southampton! With incredible upscale amenities, an alluring private pool, wraparound deck with bay views, exclusive access to a pristine natural...
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    Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    2.8 kilometres from Stony Brook Southampton
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • Parking
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Hampton Bay Home Getaway -- 2500sqft, 3br (sleeps 12) - 3 full bths & 1 half bth (HUGE Master Suite), sitting rm w/fp, living rm, dining rm, eat in kitchen, billiard room & game room -- Large Backyard w LARGE in-ground heated pool, wood burning fire pit, barbecue grill, sand volleyball...
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    Hampton Bays, Southampton
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
    2.8 kilometres from Stony Brook Southampton
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunny & Peaceful home within walking distance to the bay and a 15 min bicycle ride to the ocean. With an outdoor fireplace, outdoor shower and spacious backyard the day doesn't have to end. Master bedroom has a queen bed, daybed, and en-suite bathroom. The second bedroom has two full beds....
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    Hampton Bays, Southampton
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.8 kilometres from Stony Brook Southampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seahaven resort motel is conveniently located in Southampton.Near to beaches l,golf course and shopping. All the rooms have queen or king beds,mini refrigerator and microwave. Situated in Southampton, this motel is within 3 mi (5 km) of Meschutt Beach, Shinnecock Hills Golf Course, and Shinnecock...
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    Southampton, Hamptons
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    5.0 kilometres from Stony Brook Southampton
    4 Bedrooms, 10 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Grill
    • Ocean Views
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Getaway to this charming Cottage on the water with spectacular views!! 3 Bedrooms & Baths in the main house with a separate 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...
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    Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 10 Bathrooms, Sleeps 10
    5.2 kilometres from Stony Brook Southampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A family place with wrap-around windows and skylights gives you the best of the Hamptons. Big beautify yard and gardens, magical garden-set pool, hot-tub and plenty of room for privacy, makes it a family dream. Backyard. 3 decks. Pool set amongst Maples and hibiscus. BBQ grill. Fresh herbs....
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    Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Great Rates in 2019- No Increases In Rates and Over Holiday Weeks1 / 17
    (9)Excellent
    0.1 kilometres from Stony Brook Southampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Outdoor Dining Area
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2015
    This house turned out to be the perfect house for my wife and I, and our dog Maggie,,,,,,It was most comfortable and had all the necessary things needed for a good beach...
    Reviewed 26 July 2015
    We (family of 4, two teenage kids, boy 15 and girl 17) rented the above accommodation for 10 days in June. I could not recommend this house highly enough as I place from which...
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    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...
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    Hampton Bays, Southampton
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.1 kilometres from Stony Brook Southampton
    4 Bedrooms, 11 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 THIS HOUSE HAS 4 BEDROOM TWO OF WHICH ARE...
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    Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 11 Bathrooms, Sleeps 8
    4.3 kilometres from Stony Brook Southampton
    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Sauna
    • Housekeeping Included
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Magnificent private Southampton estate located within minutes to the charming Southampton village. Visit the top rated Coopers Beach and Hampton Bays with its many great restaurants and marinas only 2.5 miles from the estate. New amenities include: Outdoor Heated Gunite pool, outdoor shower, 90 jet...
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    Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
    Majestic Southampton Waterfront Estate1 / 36
    (7)Excellent
    4.5 kilometres from Stony Brook Southampton
    7 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Southampton, Hamptons
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 18
    Spectacular Family Resort in Hampton Bays, NY1 / 30
    (5)Excellent
    1.3 kilometres from Stony Brook Southampton
    7 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • DVD Player
    • Waterfront
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2016
    This house was amazing, it had enough bedrooms and bathrooms for me and my family. It also was great for the kids giving them their own game room downstairs while we got to...
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    About this property
    Huge 7 bedroom contemporary with 4 1/2 baths, huge deck, in-ground pool, outdoor bar, 7 person hot tub, gas BBQ. Spectacular recreation room, wonderful for entertaining. Fully loaded kitchen, 10 minute drive to ocean beach, near restaurants, clubs and all. This luxury home is available for...
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    Hampton Bays, Southampton
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 18
    Secluded Mini Estate in Hamptons1 / 25
    (6)Very good
    2.1 kilometres from Stony Brook Southampton
    9 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Waterfront
    • Wi-Fi
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2016
    My family and I stayed here for our annual family reunion. We had the best time of our lives. The pool was clean and heated and the hot tub was perfect for those cool nights. My...
    Reviewed 15 July 2015
    This was truly a beautiful home with all the amenities we needed. The pool was sparkling clean and the hot tub super warm. We were amazed at how large all the bedrooms were. The...
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    About this property
    Walk to beach. Enjoy sunsets over the bay in this beautifully designed contemporary central hall Colonial on 1.6 acres. Extremely large 9 bedrooms, 3.5 baths with state-of-the-art kitchen, formal dining room, large living room with fireplace and billiard room , ping pong room and full exercise gym....
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    Hampton Bays, Southampton
    Holiday Rental House - 9 Bedrooms, 4 Bathrooms, Sleeps 18
    4.1 kilometres from Stony Brook Southampton
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Hot Tub
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Southampton, Hamptons
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    3.5 kilometres from Stony Brook Southampton
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Hot Tub
    • Patio
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful custom designed house is located in a prestigious area of the Hamptons. Enjoy the seclusion and privacy of 1.3 acre of wooded grounds. The indoor patio, outdoor deck around the pool, 7 person hot tub, outdoor shower, Olympic size pool and wet bar in the recreation room makes for...
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    Hampton Bays, Southampton
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 14
    2.7 kilometres from Stony Brook Southampton
    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Hot Tub
    • Grill
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunsets on the Beach, Walk in the Woods Inspired by Walden, Thoreau and Emerson, Shell House is the quintessential luxury rental in the Hamptons. Dock in the nearby marina or rent a boat for the day. Shell House is your gateway to world class fishing, sprawling vineyards and quaint villages...
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    Hampton Bays, Southampton
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
    2.3 kilometres from Stony Brook Southampton
    7 Bedrooms, 1 Bathroom, Sleeps 16 Quick View
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    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A dream within reach. This unique home offers the best in indoor/outdoor living. The cathedral ceilings and interior with incredible finishes flow seamlessly into distinctive gardens on an acre of beautifully landscaped grounds. The new Olympic sized luxurious heated swimming pool and 7 person hot...
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    Location Information
    Hampton Bays, Southampton
    Holiday Rental House - 7 Bedrooms, 1 Bathroom, Sleeps 16
    3.4 kilometres from Stony Brook Southampton
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For your next getaway, make plans to stay at this stupendous 6-bedroom, 2-bathroom Hampton Bays vacation rental house! Featuring a private in-ground pool, sleeping space for 12 and bay rights with easy access to sandy shores, this New York property is poetry in motion! -- THE PROPERTY -- Master...
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    Hampton Bays, Southampton
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    2.8 kilometres from Stony Brook Southampton
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seahaven resort motel is conveniently located in Southampton.Near to beaches l,golf course and shopping. All the rooms have queen or king beds,mini refrigerator and microwave. Situated in Southampton, this motel is within 3 mi (5 km) of Meschutt Beach, Shinnecock Hills Golf Course, and Shinnecock...
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    Southampton, Hamptons
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 1
    1.4 kilometres from Stony Brook Southampton
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Washer
    • Waterfront
    • Wi-Fi
    • Patio
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy panoramic ocean and bay views from this newly renovated three story 2700 sq ft private retreat. Windows welcome natural light and ocean breezes at every turn. Open floor plan flows from gourmet kitchen and dining area to sitting space and living room centered on a beautiful floor to ceiling...
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    Hampton Bays, Southampton
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    2.5 kilometres from Stony Brook Southampton
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking to get away from the stressors of life in the city? Venture out Long Island to this Hamptons Bay vacation rental and leave it all behind! This 2-bedroom, 2-bathroom home boasts the amenities necessary for an unforgettable city-break. Start your morning with a stroll along Ponquogue Bay and...
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    Hampton Bays, Southampton
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4.4 kilometres from Stony Brook Southampton
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Central Heating
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking to get away from the city stresses? Leave them all behind and head to this Southampton vacation rental home! Call this 3-bed, 2-bath property your home base during your city escape and find yourself less than 4 miles to Southampton's famed village full of shopping and gourmet restaurants....
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    Southampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    1.8 kilometres from Stony Brook Southampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Washer
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hamptons Beach House Perfection Enjoy this family- (and dog-) friendly beach house in a great location, minutes from both bay and ocean beaches, restaurants, and shopping. Featuring a fenced-in backyard, the home has a nautical theme, with high-end interior design touches, hardwood flooring, and a...
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    Hampton Bays, Southampton
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.0 kilometres from Stony Brook Southampton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    House is located on a culdesac in a quiet neighborhood very central to town and beaches. Two bedrooms and a bath located on the second floor and two bedrooms and a bath located on the first floor. Laundry room and additional space are available in the basement. House has an in-ground heated pool...
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    Hampton Bays, Southampton
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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