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Southampton House Rentals

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    Travellers to Southampton are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    31 Matching Rentals in SouthamptonView all 59 rentals
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    4 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Very Private and Tranquil  House in wooded estate.1 / 20
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 September 2017
    Let me share my impression in short: very convenient location, exceptional cleanliness in rooms, outdoor pool, beautiful plot, very friendly host Lydia. There is not better...
    Reviewed 15 August 2017
    Wonderful casa tua! Very welcoming , beautiful house , gracious hosts , great breakfast and beautiful backyard and pool.Highly recommend!
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    About this property
    This well-appointed and maintained 2,200 sq.ft., 4 bedroom, 3 bath Contemporary has a bright sunlit breakfast area directly off the gourmet kitchen, Situated on a sprawling manicured acre with a 20x40 sparkling swimming pool and directly across the street from the fascinating Peconic Bay with...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Immaculate 4BR Southampton House w/Private Pool!1 / 32
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
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    • Internet Access
    • Hot Tub
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    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 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 23 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 4-bedroom, 4-bathroom Southampton vacation rental home, which sleeps 8! 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 11968
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Housekeeping Included
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    In the front is a beautiful woodland garden with rare woodland flowers and ferns, moss-covered boulders and miniature ponds. In the rear is a Japanese garden, complete with a moon bridge over a babbling brook, a waterfall you can swim behind, a pond house with a deck you can sunbathe or dive from,...
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    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    • Washer
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    • Private Outdoor Pool (Unheated)
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located in Southampton. It has 4 bedrooms and sleeps 10. If you have been wanting to visit the Hamptons this house is the perfect choice since it’s perfectly located in the heart of the Hamptons. Just a three minute drive to the village with all the wonderful restaurants,...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    15 Bedrooms, 17 Bathrooms, Sleeps 30 Quick View
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    • Patio
    • Ocean Views
    • Washer
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In Real These Are 3 Houses That Can Be Separately Rented also together. House 1 6 Bedrooms 8.5 Bathrooms 12 Sleeps Price Range $1400/N (Wknd) $2100 Damage Deposit $500 Cleaning Fee $450 House 2 Bedroom 3 Bathroom 2.5 Sleeps 6 Price Range $780/N (Wknd) $1760 Damage Deposit...
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    Southampton, Hamptons 11968
    Holiday Rental House - 15 Bedrooms, 17 Bathrooms, Sleeps 30
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    Amazing Luxury Southampton Home--6BR Pool Jacuzzi Beach (Hamptons Classic)1 / 32
    (1)Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
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    • Hot Tub
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    The house was beautifully decorated and felt very homey. It was a great place to stay for a long weekend in Southampton. Very easy to get into town and to the beach, but it was...
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    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, and is next to a gorgeous nature...
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    Southampton, Hamptons 11968
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    It's a 3 bedroom, 2 bath home. 2 Family room, one with a TV and one for reading and watching the sunset over Fish Cove through a large window. The master bedroom with en suite bathroom is located on one side of the house while the guest bedrooms are on the other side, so complete privacy. The...
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    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Southampton, this 6 bedroom home is 8 km from Agawam Park. Southampton 6 Bed with Pool features a grand entrance, kitchen area with marble counters, stainless steel appliances and French doors with an outside seating area. The living room offers an archway with a fireplace and separate...
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    Southampton, Hamptons 11968
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    • Hot Tub
    • Patio
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is in the most desirable neighborhood in Southampton. Close to everything the Hamptons have to offer. You'll be near the beaches and the Village of Southampton - where you have many exciting restaurants, shops, movie theater, and night celebrities. When it's time to relax, walk back in...
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    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
    • Cable/satellite TV
    • Patio
    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautiful Southampton Home w Pool/Jacuzzi Near Beach & Town Sleeps 141 / 32
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    • Hot Tub
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    Great location and close to town. Pool and Jacuzzi are beautiful. Would definitely recommend to anyone looking for a nice weekend out east.
    Reviewed 8 July 2017
    Recently spent a week in the Shinnecock Hills home. It way exceeded my expectations. The house is a perfect setup and size for a large shared group or family. There is plenty of...
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    About this property
    Beautiful Southampton home located in the heart of the Hamptons. Very private with a large pool and jacuzzi. Just a three minute drive to the village with all the wonderful restaurants, clubs and small beaches and award winning vineyards. The home is clean, stylishly decorated, and steps away...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Wi-Fi
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    Southampton, Hamptons 11968
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • DVD Player
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    • Internet Access
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pack your bags for an unforgettable East Coast escape at this 3-bedroom, 2.5-bathroom Southampton vacation rental house. Boasting 2,500 square-feet of luxurious living space, this home offers sleeping accommodations for up to 6 guests, a covered front porch and a spacious back deck. Take full...
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    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your best spot for the greatest game's annual championship. South of the highway and perched on a Shinnecock hill, this two story house with artist's loft is surrounded by decks. This paradise if very private. It has a gated pool and generous parking. Perfect for a family reunion in the Hamptons....
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    Location Information
    Southampton, Hamptons 11698
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hilltop Hideaway in Southampton, this lovely turn of the century house was recently renovated and appointed with new high end chic furnishings. Spacious 4 bedroom, 3 bathrooms. Central air conditioning throughout. Large living room with fireplace, stainless steel and granite kitchen, formal dining...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 11 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    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 11968
    Holiday Rental House - 4 Bedrooms, 11 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Southampton, Hamptons 11968
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan your next Hamptons family vacation at this modern 3-bedroom, 2-bathroom vacation rental house within walking distance of the Smithtown Bay! This spacious 1,700-square-foot farmhouse offers 8 lucky guests a beautifully furnished interior with whitewashed wood beams, double height ceilings, and...
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    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 10 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
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    Pet friendly
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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...
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    Southampton, Hamptons 11968
    Holiday Rental House - 5 Bedrooms, 10 Bathrooms, Sleeps 16
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Waterfront
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    • Ocean Views
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Southampton, Hamptons 11901
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    10 Bedrooms, 9 Bathrooms, Sleeps 22 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This estate features the most exquisite blend of old world charm and new. Originally dating back to the year 1882, this fabulous farmhouse underwent a meticulous renovation and expansion. The end result : A luxurious 7 Bedroom, 6.5 bath Main house, and 3 Bedroom, 2 Bathroom Guest House. In the...
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    Southampton, Hamptons 11968
    Holiday Rental House - 10 Bedrooms, 9 Bathrooms, Sleeps 22
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    The Space Located in Southampton less then a half a mile from the quite beaches of Peconic Bay, this house is also just a 10 minute drive to Sag Harbor or Southampton Villages. Close to ArtHampton (5 mi), Art Market (5 mi) and Hampton Classic Showgrounds (6.5 mi)! The house has 4 bedrooms, three...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
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    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
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    • Private Outdoor Pool (Unheated)
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    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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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