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Holiday Rentals with Pools in Southampton, NY

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    €1,178 Average
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    Travellers to Southampton are booking May dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 27
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    1 / 55
    5 of 5 stars (7) Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    1 / 23
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    1 / 50
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    About this property
    We had a cancellation so most of August and Labor Day are available. This open-plan house with second floor gallery and home theater in the basement brings the outdoors in. Wrap-around windows and skylights (plus an AC system with a stun button) gives you the best of the Hamptons. Big beautify... View all property information
    Location Information
    Southampton, Hamptons
    1 / 25
    5 of 5 stars (1) Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Recently renovated, beautiful vacation home within a mile of Southampton Village restaurants and shops. It is located on a very quiet and private lane near two beautiful horse farms. This home features six large bedrooms and four and one half baths. The floor plan is open, bright and airy, with... View all property information
    Location Information
    Southampton, Hamptons
    5 of 5 stars Reviewed 30 June 2015
    The house was very nice, clean and had everything we needed and more. The owners were very nice and accommodating. We were a group of 12 and were all very comfortable. We all...
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    1 / 28
    4 Bedrooms, 5 Bathrooms, Sleeps 7 | Quick View
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    • Patio
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    About this property
    Welcome to your private Hamptons escape! This immaculate Southampton vacation rental house is sure to provide the perfect vacation spot for your next family getaway. Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this gorgeous home is a terrific size and... View all property information
    Location Information
    Southampton, Hamptons
    1 / 17
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Wi-Fi
    • Private Garden
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    • x
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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... View all property information
    Location Information
    Southampton, Hamptons
    1 / 12
    5 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Traditional 5 bedroom house on 1.5 acres south on Flying Point Road. Beautiful, mature gardens and heated pool. tons of living space and finished basement.Wood burning fireplace. large family room, library, double living room, two separate wings for sleeping and beautiful patio. gas barbecue.... View all property information
    Location Information
    Southampton, Hamptons
    1 / 11
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
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    • Waterfront
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    • Pet-friendly
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    • x
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    • x
    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... View all property information
    Location Information
    Southampton, Hamptons
    1 / 24
    4 Bedrooms, 10 Bathrooms, Sleeps 8 | Quick View
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    • Secure Parking
    • Patio
    • Children's Pool
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    • Pet-friendly
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    • x
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    • x
    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,... View all property information
    Location Information
    Southampton, Hamptons
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    1 / 13
    4 Bedrooms, 10 Bathrooms, Sleeps 10 | Quick View
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    • Ocean Views
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    • Pet-friendly
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    • x
    • x
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    • x
    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... View all property information
    Location Information
    Southampton, Hamptons
    1 / 16
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Southampton, Hamptons
    1 / 32
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Internet Access
    • Hot Tub
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    • Waterfront
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Southampton, Hamptons
    1 / 38
    5 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Washer
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Private Indoor Pool
    • Waterfront
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Custom Vacation Home set up for family relaxation and fun, with boating and sailing from premises, one mile from world class ocean beach, restaurants and railroad into New York City. We are west of the Shinnecock Canal away from the crowd and traffic in a quiet private neighborhood on private sandy... View all property information
    Location Information
    Southampton, Hamptons
    1 / 22
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Balcony
    • Satellite TV
    • Patio
    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Southampton, Hamptons
    1 / 24
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    • Hot Tub
    • DVD Player
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    • Private Outdoor...
    • Satellite TV
    • Washer
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This one has it all! On two acres of private land, boasting 6,500 square-feet of beautiful and elegant interior spaces, decorated by a noted interior designer. There are six en-suite bedrooms (master bedroom pictured), five and one-half baths, a heated oversized 20' x 50' Gunite pool with adjacent... View all property information
    Location Information
    Southampton, Hamptons
    1 / 7
    6 Bedrooms, 7 Bathrooms, Sleeps 14 | Quick View
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    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Waterfront
    • Sauna
    • Washer
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    waterfront villa estate with;everything!!!!! Beds: 3 King Beds, 2 Queen Beds, 1 Double Bed, 2 Sofa Beds, 1 Crib View all property information
    Location Information
    Southampton, Hamptons