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Holiday Rentals with Pools in Southampton

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    Travellers to Southampton are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    32 Matching Rentals in SouthamptonView all 62 rentals
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Post Modern Quaint Home Near  Beach1 / 71
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 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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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    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 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    'Pennies From Heaven'1 / 25
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    Reviewed 22 June 2016
    House and groundsI stayed at this property with my boyfriend and another couple for a long weekend. It was great!! It was a super easy drive from the city and upon arrival, we...
    Reviewed 13 June 2016
    We had a terrific stay with our family at this prefect private get away that offers it all . Set on a private cul de sac for peace and quiet yet minutes from town, shopping...
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    About this property
    Summer house that has it all! This 4 BR/3 Bath newly updated property, sits on a 1/2 acre lot with a newly lined in-ground pool with Trex decking surround and features an open concept main living space, entertainment space, high end finishes and tons of privacy. Local Realtors have identified this...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    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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    15 Bedrooms, 17 Bathrooms, Sleeps 30 Quick View
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    • Patio
    • Ocean Views
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    • Waterfront
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    Pet friendly
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    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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    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    • Private Garden
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    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 11946
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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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
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    • Cable/satellite TV
    • 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, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    • 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. (THIS HOUSE REQUIRES A 5 NIGHT MIN...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Outdoor Pool (Unheated)
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is Close to everything the Hamptons have to offer , your family will love this house and it's fantastic location!! In the area within a few block walk you will find many exciting restaurants, shops, movie theater, beach bars, and Jet Ski & boat rentals within 1 mile from the home. You...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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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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    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
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    • Wi-Fi
    • Grill
    • Secure Parking
    Suitability
    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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    4 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
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    • Patio
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    • Private Outdoor Pool (Heated)
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to your private Hamptons escape! Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this immaculate Southampton vacation rental house is sure to provide the perfect spot for families or a close group of friends traveling together. Boasting a beautiful...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 7
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Waterfront
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    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 11968
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    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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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    • Patio
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your own private summer resort. This house has it alll, you won't want to leave! Waterfront dock, jacuzzi, sparkling pool, multiple patios, 2 outdoor grills, and multiple balconies are key outdoor features. State of the art kitchen, large country dining room table, 2 fireplaces, 2 open airy...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Hamptons private beach front home + pool1 / 17
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Ocean Views
    • Washer
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    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly refurnished and upgraded Hamptons Beach House. Amazing bay views from every room. Heated pool and private sandy beach. Ideal for large families. Swim in the bay or your own pool. This home is on the border of Shinnecock Hills and Hampton Bays making it very desirable due to its...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large swimming pool (43' x 22' free form) with changing colors LED lights and water fall, a 10 people outdoor spa jacuzzi tub. Complete and well equipped outdoor kitchen, walking distance to the bay and 5 minutes drive to town or the OCEAN. Big and clean house in the woods. The house indulge...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 10 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    • Ocean Views
    • Balcony
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    • Private Outdoor Pool (Heated)
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    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 11968
    Holiday Rental House - 4 Bedrooms, 10 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
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    • Waterfront
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    • 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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    Location Information
    Hampton Bays, Southampton 11946
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
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    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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    Southampton, Hamptons 11698
    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
    Kid friendly
    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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    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    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 heated pool, sleeping space for 12 and beach rights with easy access to the bay and sandy shores, this New York property is poetry in motion! THE...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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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 town! Very private with a large pool and large Jacuzzi. The house sleeps 14 and...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    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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    SECLUDED BEACH CONTEMPORARY ESTATE1 / 23
    (3)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
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    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2016
    Our family had a lovely time during our stay at this house, the amenities were great and we had a warm welcome when we got there. the pool, hot tub, and game room were all above...
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    About this property
    Only 600 feet from one of the most beautiful (private) Hampton's beach. Enjoy poolside living in this stunning contemporary home complete with lots of skylights and cathedral ceiling. Bike along the Peconic Bay or enjoy miles of sandy beach just steps away. This spacious home has a large heated...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    Majestic Southampton Waterfront Estate1 / 55
    (7)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Wi-Fi
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    Pet friendly
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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...
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    Southampton, Hamptons 11968
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 18
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    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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    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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    4 Bedrooms, 10 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Patio
    • Children's Pool
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    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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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 10 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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