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Holiday Rentals with Pools in Southampton

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    ₹ 77,247 Average
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    Travellers to Southampton are booking July dates now. Secure your holiday home today, and have the perfect trip.
    37 Matching Rentals in SouthamptonView all 113 rentals
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Immaculate & Spacious 4BR Southampton House w/Wifi, Firepit, Dazzling Private Pool & Spectacular Bay Views from Wraparound Deck - Only 200 Feet From Private Beach Access!1 / 32
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Air Conditioning
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    • Hot Tub
    • Satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    My husband and I stayed here over the fall for the long weekend. The house and décor were truly beautify, exactly what you’d think of for Hamptons style. It had big bay windows...
    Reviewed 22 May 2017
    Came here for a couples getaway with my wife and some friends. Had a great time and ended up inviting some friends from CT to join us when we realized the house sleeps many more...
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    About this property
    Experience the exquisite relaxation of upper Long Island, New York by staying at this luxurious Southampton vacation rental home! With incredible upscale amenities, an alluring private pool, exclusive access to a pristine natural sand beach and close proximity to all the world-class attractions for...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Very Private and Tranquil  House in wooded estate.1 / 20
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Satellite TV
    • Private Outdoor Pool (Unheated)
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    In our travels, both short and long, at home and abroad, we always prefer to stay in small hotels or B & B. We try to avoid a large crowd and associated fuss, noise and...
    Reviewed 22 May 2017
    Beautiful location with charming style and impeccable hospitality, delicious gourmet breakfasts, cozy and warm rooms, beautiful gardens and a pool. Lydia and Kazimir are the...
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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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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    • Hot Tub
    • Private Outdoor Pool (Heated)
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    • Satellite TV
    • 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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Satellite TV
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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” House, 5 bedrooms, 5 baths , CAC, hardwood floors, in-ground heated pool, Outdoor...
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    Southampton, Hamptons 11946
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    • Satellite TV
    • Secure Parking
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    • Private Outdoor Pool (Unheated)
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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, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    • DVD Player
    • Hot Tub
    • Patio
    • Wi-Fi
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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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Chic Sunny Private 2 bedrm Cottage (93 miles frm NYC) that step out on to your own secluded patio w/outdoor furniture + gas grill for easy BBQ meals. Cottage guests hv their own gate entry to the pool. You are minutes from World Famous Cooper's Beach, convenient to Village Shopping +Restaurants....
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    Southampton, Hamptons 11968
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    • 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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    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
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located in Southampton. The house is nestled in a park like setting with a private tree-lined yard. You will have all the privacy you want. Enjoy a beautiful built in pool with hot tub. The home is clean, stylishly decorated, and steps away from a gorgeous nature preserve. (...
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    Southampton, Hamptons 11968
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    • Hot Tub
    • Washer
    • Grill
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Southampton home. Very private with a large pool and a beautiful, large Jacuzzi. This home is perfectly located in Southampton. Sleeps 13. If you have been wanting to visit The Hampton's for the first time house is the perfect choice since its perfectly located in the heart of the...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • DVD Player
    • Washer
    • Satellite TV
    • Hot Tub
    • Grill
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Be close to everything the Hamptons has to offer while getting away from it all in your little piece of paradise.! You'll be a mere 1 mile away from the ocean beaches of and in close proximity to the Hampton Village of Southampton - with its exciting selection of restaurants, shops, movie theater,...
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    Southampton, Hamptons 11968
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Washer
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is modern, clean and comfortable. few blocks to social club and 75 main!! It is located in the heart of the Southampton! The house is located just a few blocks from the Village of Southampton and a few blocks from the most beautiful beaches in the world. It is in one of the most desirable...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Hot Tub
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located in Southampton. It is a 4 Bedroom, sleeps 10. If you have been wanting to visit The Hampton's for the first time this house is the perfect choice since its perfectly located in the heart of the Hampton's, just a three minute drive to the village with all the...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Freshly renovated Shinnecock Villa, two bedrooms, 2.5 baths, 52-foot great room giving on to generous fenced yard and 45-foot gunite pool. Just steps to Shinnecock Bay and minutes to Southampton Village. Fully-equipped chef's kitchen featuring double wall oven, two dishwashers, Sub-Zero...
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    Southampton, Hamptons 11968
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 4 bedroom, 3 bath unique home is located South of the highway, with water views! Enjoy your summer sitting by the heated pool or play basketball. The house was recently renovated with all new baths, master has steam shower and new kitchen.and appliances, HVAC, interior/exterior lighting and...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 4
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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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    • 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<BR>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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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Fully completed, this stunning home situation on a private acre in Southampton Village is close to village and beaches. With over 5300 sq. ft with an additional 2000 sq ft of lower level living space, this 7 bedroom, 7 bathroom home has everything you could possibly want. A double height entry...
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    Southampton, Hamptons 11968
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly Renovated and Redesigned in 2015, This Southampton Village Home Is Ready to Move Right In! The Main floor Features a Master Bedroom En-Suite with Sliding Doors to Outside Deck and Small Study, Living room with Private Sitting Area, Gourmet Chefs' Kitchen with Wolff Stove, and Sub Zero...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    • Waterfront
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    • Satellite TV
    • Hot Tub
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is extravagant living at its best. Picture yourself enjoying expansive water views and majestic sunsets. The park like setting lends itself to an idyllic outdoor paradise. This home has 7 huge bedrooms and 5 palatial bathrooms. The house boasts a wide-open floor plan with soaring cathedral...
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    Southampton, Hamptons 11968
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 18
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
    • 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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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2-Story 2 bedroom 2.5 bath located in the village and close to the beaches. Beautiful grounds with private patio, community pool and tennis. Must Be 18 & Older To Book. We offer bonuses: Discounted Lyft Rides, Zip Car, &? More........
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    Southampton, Hamptons 11968
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful Summer Home Located off a private road in Southampton. A Must see!! Property is equipped with four-bedroom, two-bath with open living room with fireplace, dining room, kitchen, central air-conditioning, Heated Pool, & Full Basement. We do offer bonuses: Discounted Lyft Rates, Zip Car,...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 10 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    Just a close distance to Main Street, shops and the amazing ocean beach. This home's living room has a fireplace and french doors going to wrap around porch and lovely heated pool. Open kitchen and dining room. It has a bright bedroom and 3.5 baths. Expansive rear yard with lovely landscaping will...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Close to town and ocean beaches. This bright and clean 5 bedroom, 5.5 bath home in Southampton village. Featuring a large living room with fireplace, formal dining room, media room, and a chef's kitchen. There is a spectacular master suite with fireplace and separate sitting room, a heated gunite...
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    Southampton, Hamptons 11968
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This great Summer Home is set on a private full acre giving it a quiet and secluded country feel like few other homes in the Village. Property features 4 bedrooms and 3.5 baths, a living room with a vaulted ceiling and a kitchen with new appliances which opens up to the pool area, 2 fireplaces as...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just a close distance to Main Street, shops, restaurants and ocean beaches. A nice living room with fireplace and french doors going to wrap around porch and lovely heated pool. Open kitchen and dining room. 4 bright bedrooms and 3.5 baths. Expansive rear yard with lovely landscaping will make you...
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    Southampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    Wonderful home featuring 5 beautifully furnished bedrooms, 5 and a half bath rooms, on a very quiet area in Southampton north. Beautifully designed eat-in kitchen with French doors leads to a wonderful outdoor area to entertain. Manicured gardens and a exquisite heated pool. This Southampton home...
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    Southampton, Hamptons 11968
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully renovated seven bedroom, five bath, two-story home that holds on to its 19th century architectural roots while embracing the conveniences of modern day. Well-appointed throughout, additional features include a state-of-the-art kitchen, formal dining room, three fireplaces, original...
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    Southampton, Hamptons 11968
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Hot Tub
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Patio
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two-story Southampton Traditional sits on nearly 3+/- acres and enjoys several magnificent amenities and attributes, including seven bedrooms and six and one half baths. The living room has a cathedral ceiling, a fireplace, windows rising nearly to the rooms full height and French doors...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    8 Bedrooms, 7 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully appointed elegant home with the latest smart home technology is must see luxurious summer rental. Set on 1.5 manicured acres this 7400 sq ft home has 8 bedrooms 6.5 baths, formal living and dining, pool house pavilion, and state of the art media room. Filled with light in every...
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    Location Information
    Southampton, Hamptons 11968
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 6
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