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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.
    34 Matching Rentals in SouthamptonView all 75 rentals
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    Post Modern Quaint Home Near  Beach1 / 142
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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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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    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Sauna
    • Housekeeping Included
    • Hot Tub
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fabulous Southampton Luxury Mansard completely private and renovated in 2018 with amazing entertaining spaces and Beautiful 20' x 40' Heated Gunite Pool. Two outdoor fire pits, Sonos music inside and out. 4 Bedrooms with (5) queen beds and (1) King Bed Master Suite. 2 miles to Southampton Village...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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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
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 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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    'Pennies From Heaven'1 / 25
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Grill
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    • Private Outdoor Pool (Unheated)
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    • Patio
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 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 12 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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    Southampton Waterfront- Beach Home- 2 kayaks!1 / 28
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2018
    Spacious and well maintained home. Wonderful and responsive owner.Especially loved the lofted ceiling, great room, huge kitchen island, master suite with big walk-in closet and...
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    About this property
    ***PLEASE INQUIRE FIRST (EMAIL OWNER) BEFORE INSTANT BOOKING!!.. 631 - 365 - 3828 Located east of the canal on the beautiful Peconic Bay, over 100 feet of sandy beach, walk down the shore to for food, drinks and entertainment! Beautiful, crystal clear water, 5000 sq ft custom Waterfront “GREEN”...
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    Southampton, Hamptons 11946
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For adults over 26 years kids OK please INQUIRE first with your details for availability min. 2/3 nights depends date. EXTRA to price on screen at CHECK- IN: 180$ cleaning fee/stay ,refundable security deposit 500$-3.5K (depend dates,number of guests and age range) security deposit refund max 24h...
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    Hampton Bays, Southampton 11946
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    • Wi-Fi
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    • 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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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Hot Tub
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Cable/satellite TV
    Suitability
    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 and 5 min drive to the famous Coopers...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Romantic Getaway in Southampton (private room/bathroom)1 / 14
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2018
    Great location. Beautiful grounds. Gracious host. The home was easy to find, peaceful and located in an area of that made getting around central Long Island simple and...
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    About this property
    Newly renovated house with nice spacious rooms with comfortable new double beds. Double occupancy room /private bathroom/entrance, queen size bed newly renovated 4 bedroom-3 bathroom home in prime Southampton location. Close to bay, beach and town. Directly across the street from the fascinating...
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    Southampton, Hamptons 11968
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    8 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Washer
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 bustling with charming shops. With a resort...
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    Location Information
    Hampton Bays, Southampton 11946
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 20
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
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    • Patio
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    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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    Location Information
    Hampton Bays, Southampton 11946
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This one level ranch house has the advantage of being in the Village of Southampton, south of the HWY, 3 short blocks to the train. Walk-able location to many places to eat and shop. Priced to rent, according to the condition of the house - retro 60's. House is clean, Full of sunlight, comfortable,...
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    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
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    • Internet Access
    • Mountain Views
    • Hot Tub
    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 11946
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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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)
    • Internet Access
    • Patio
    • Cable/satellite TV
    Suitability
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Internet Access
    • Hot Tub
    • Patio
    • Washer
    • 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 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Housekeeping Included
    • Washer
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
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    • Washer
    • DVD Player
    • Grill
    Suitability
    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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    Southampton, Hamptons 11698
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Beautiful Southampton Home w Pool/Jacuzzi Near Beach & Town Sleeps 141 / 38
    (3)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 28 June 2018
    This was everything we wanted. The space was big enough to fit my family of 6 and 3 guests very comfortably. We LOVED the pool area with the hot tub and pool house. We...
    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.
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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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    Location Information
    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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    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, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    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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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
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    • Internet Access
    • 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 7
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    • Hot Tub
    • 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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    4 Bedrooms, 10 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Grill
    • Ocean Views
    • Balcony
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    • Private Outdoor Pool (Heated)
    • Hot Tub
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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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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 10 Bathrooms, Sleeps 10
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    • Hot Tub
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    • 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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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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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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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Air Conditioning
    • Patio
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    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The home offers the most spectacular sunsets the Hamptons has to offer. All bedrooms have Tv's , the house is close to Village of Southampton and a close drive to Sag Harbor, Bridgehampton & East Hampton. Profesionally Decorated the Bayfront is comfortable and inviting. The Chefs Kitchen with...
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    Location Information
    Hampton Bays, Southampton 11946
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    • Grill
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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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
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    • 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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
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    • 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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    Location Information
    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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    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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    4 Bedrooms, 10 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 10 Bathrooms, Sleeps 8
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