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Southampton Holiday Homes

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    Travellers to Southampton are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 75 Rentals in Southampton
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Newly renovated, totally updated. Well done 3+Br 2 bths, 5 minutes drive to town ( train station, super market, restaurant, cafe, bar…….) 10 minutes drive to Ponquogue Beach and 5 minutes walk to great peconic bay beach Any things to do near by the house ~ Tanger outlet ( 15 mins ) ~ Any...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    About this property
    Guests are sure to enjoy a memorable vacation in this fully furnished, 6 bedroom/ 7 bath home in a private, gated, park like setting. The 3 master bedrooms have 2 bedrooms with a king-sized bed, 1 with a queen size bed while the remaining rooms are furnished with a full-sized bed (2) and bunk...
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    Southampton, Hamptons 11968
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    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...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Central Heating
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    Pet friendly
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    About this property
    Situated at the end of a very quiet private road in an old estate neighborhood right on the water in the eastern end of North Sea, Southampton . With 3 bedrooms, 2 baths, a big chef’s kitchen with 36' Viking range with electrical oven and Miele Washer/Dryer and a big fireplace with comfortable...
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    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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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 11968
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    COZY GUEST COTTAGE on the open bay attached to main house. Plenty of space with your own BBQ, new appliances and fresh paint. Near all train, restaurants, shopping, movie theater, 7/11, Starbucks, Dunkin Donuts, fishing, boating and swimming. Go East to Montauk Point in 1 1/2 hours or go West...
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    Hampton Bays, Southampton 11946
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    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
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    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 11946
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully decorated English Tudor set in quiet cul-de-sac. Ten-minute drive or two-block walk to shuttle to Shinnecock Golf Course for the 2018 Golf US Open! A short walk to Good Ground Park for outdoor concerts, walking/ biking trails, and shuttle for car-free access to beaches! Walk to village...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Terrace
    • Hot Tub
    • Private Garden
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Southampton, Hamptons 11968
    Holiday Rental House - 5 Bedrooms, 10 Bathrooms, Sleeps 16
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
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    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 11968
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
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    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 11968
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • 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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    Location Information
    Southampton, Hamptons 11968
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • 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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    Location Information
    Southampton, Hamptons 11968
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Hot Tub
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located in the town of Southampton. The house is nestled in a quiet park-like setting with a private tree-lined yard. You will have all the privacy you want. Enjoy a beautiful built in pool with jacuzzi. The home is clean, stylishly decorated. This home is centrally located...
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    Southampton, Hamptons 11968
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 10 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Patio
    • Children's Pool
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 10 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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,...
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    Southampton, Hamptons 11968
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • 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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    Location Information
    Southampton, Hamptons 11968
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Southampton, Hamptons 11962
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Balcony
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Southampton, Hamptons 11968
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Terrace
    • Balcony
    • Parking
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Private Garden
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    water everywhere. bulkhead and dock. on wooley pond, southampton. bring your kayak or paddle and leave from your backyard, go into great peconic in short distance. large decks from various rooms in house, with water views. sit on your deck and bbq. 20x40 pool, lounges and umbrella and views. in...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home is located on quiet road in Village of Southampton. A ten minute stroll to Main St. where there is wide choice of stores and restaurants. One mile from Ocean Beaches. The garden is gated and large and pool and deck wonderfully private. House design is open, tastefully furnished and well...
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    Southampton, Hamptons 11968
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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