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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.
    53 Matching Rentals in SouthamptonView all 102 rentals
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    'Pennies From Heaven'1 / 25
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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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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    Very Private and Tranquil  House in wooded estate.1 / 20
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Post Modern Quaint Home Near  Beach1 / 71
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • DVD Player
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2018
    This house exactly served our needs for a family getaway for ourselves, our two adult daughters, their husbands, and two grandkids -- a newborn and a 2-year-old. There was...
    Reviewed 4 September 2017
    Highly recommend this house. Clean, large enough for to fit our 2 families very comfortably. Owner was very responsive.
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    About this property
    Immaculate four bedrooms, three full baths sleeps 8-10. Full gym, pool and jacuzzi nestled away in prestigious Red Cedar Ridge. Large deck with BBQ. Fully equipped kitchen. Wi-fi internet and premium channels cable tv. Pool table, basketball and children play ground for entertainment. Five min...
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    11946, Hampton Bays, Southampton
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Monthly Rental Only! Exquisite 50 foot driveway, handmade iron gated property, affording total privacy, 2 acres exquisite landscaping, flowers, vegetable garden, 2 waterfalls, gardens, stream, pond, pond beach, 30 x 40 gunite swimming pool with Rose Arbor, fruit orchard, Outdoor Kitchen & BBQ...
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    11976, Water Mill, Southampton
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Lavish Southampton House w/Private Beach & Pool!1 / 32
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 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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    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    • Grill
    • Wi-Fi
    Suitability
    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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    11946, Hampton Bays, Southampton
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
    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. Check out all our beautiful...
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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Garden
    • Secure Parking
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A truly peaceful getaway a few minutes from Southampton Village and beaches. This lovely home is recently updated and tastefully decorated with an inviting open floor plan kitchen, living and dining room that includes a working fireplace as its centerpiece. The house sits on a quiet street with...
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    Location Information
    11968, Hampton Bays, Southampton
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Hot Tub
    • DVD Player
    • 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
    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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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
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    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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    Location Information
    11946, Hampton Bays, Southampton
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    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 22 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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    Location Information
    11968, Southampton, Hamptons
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Southampton sunny beach luxury 4 bedroom home is ideally located near Southampton Village and area of farm fields, orchards, and wineries, and near to Coopers and Flying Point beaches. The home is set on a spacious property secluded by hedges and wildflower garden. The light filled living...
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    Location Information
    11968, Water Mill, Southampton
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    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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    Location Information
    11946, Hampton Bays, Southampton
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • 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
    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 10 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Grill
    • Ocean Views
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Hot Tub
    Suitability
    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
    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 10 Bathrooms, Sleeps 10
    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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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Sprawling Southampton home with pool & jacuzzi room for entire family1 / 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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    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lower Seven Ponds Haven This charming Water Mill home has been remodeled from top to bottom, showcases a clean and crisp decor and is the ideal location for your next getaway to the Hamptons. The home features a spacious kitchen complete with high-end appliances, perfect for preparing meals. Off...
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    11976, Water Mill, Southampton
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Sauna
    • Housekeeping Included
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Magnificent private Southampton estate located within minutes to the charming Southampton village. Visit the top rated Coopers Beach and Hampton Bays with its many great restaurants and marinas only 2.5 miles from the estate. New amenities include: Outdoor Heated Gunite pool, outdoor shower, 90 jet...
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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Patio
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    • Balcony
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3500 sq ft Hampton's styled home has a large light filled living room with fireplace and sliding glass doors to the expansive deck with heated pool. The open floor plan makes this home perfect for entertaining. This home is situated on .75 of an acre of property that backs up to a private...
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    11976, Water Mill, Southampton
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    7 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Sauna
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful estate home in Water Mill, New York borders the prestigious Matt Lauer's 40 acre horse farm with distant ocean views. This estate features 7 bedrooms with 7 en suite bathrooms, 2 1/2 baths, two master bedrooms. There are five full masonry fireplaces, pool room, wine room, cigar...
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    11976, Water Mill, Southampton
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 10
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
    • Secure Parking
    • Wi-Fi
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    Suitability
    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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    11968, Southampton, Hamptons
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Washer
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Well appointed 7000 sq. ft. traditional Hamptons home situated on 1.40 acres bordering a 32 acre reserve. 6 bedrooms and 5.5 baths, huge eat in kitchen, formal living and dining rooms, bar and an oversized gunite salt water pool and spa. Center foyer opens to a dining room with butler's pantry,...
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    11976, Water Mill, Southampton
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    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
    • 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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    11968, Southampton, Hamptons
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
    Hamptons Lofty Beach Barn - Pet Friendly1 / 30
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2019
    We have stayed at this property twice. It’s feels like our very own home away from home. We brought two sets of children here and enjoyed our own adult time while the kids...
    Reviewed 10 June 2019
    We booked this house for a family getaway. Amazing property. Very family friendly, plenty of space for the adults and kids to spread out. The house is very well decorated and...
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    About this property
    Lofty beach barn! decorated 3,000sf property with high-end furnishings and pool. Authentic Post and Beam Barn house located in the picturesque town of Water Mill in Southampton, NY. The area is home to the world famous Coopers Beach, Duck Walk Vineyard, Wolffer Estates, Hampton Classic, Water...
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    Location Information
    11976, Water Mill, Southampton
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Secluded Mini Estate in Hamptons1 / 25
    (6)Very good
    9 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Waterfront
    • Wi-Fi
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2016
    My family and I stayed here for our annual family reunion. We had the best time of our lives. The pool was clean and heated and the hot tub was perfect for those cool nights. My...
    Reviewed 15 July 2015
    This was truly a beautiful home with all the amenities we needed. The pool was sparkling clean and the hot tub super warm. We were amazed at how large all the bedrooms were. The...
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    About this property
    Walk to beach. Enjoy sunsets over the bay in this beautifully designed contemporary central hall Colonial on 1.6 acres. Extremely large 9 bedrooms, 3.5 baths with state-of-the-art kitchen, formal dining room, large living room with fireplace and billiard room , ping pong room and full exercise gym....
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    Location Information
    11946, Hampton Bays, Southampton
    Holiday Rental House - 9 Bedrooms, 4 Bathrooms, Sleeps 18
    Spectacular Family Resort in Hampton Bays, NY1 / 30
    (5)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • DVD Player
    • Waterfront
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2016
    This house was amazing, it had enough bedrooms and bathrooms for me and my family. It also was great for the kids giving them their own game room downstairs while we got to...
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    About this property
    Huge 7 bedroom contemporary with 4 1/2 baths, huge deck, in-ground pool, outdoor bar, 7 person hot tub, gas BBQ. Spectacular recreation room, wonderful for entertaining. Fully loaded kitchen, 10 minute drive to ocean beach, near restaurants, clubs and all. This luxury home is available for...
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    Location Information
    11946, Hampton Bays, Southampton
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 18
    Majestic Southampton Waterfront Estate1 / 36
    (7)Excellent
    7 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    Suitability
    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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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 18
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Hot Tub
    • Waterfront
    Suitability
    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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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southampton, Luxury 4 Bed 2 Bath home with pool, minutes to everything! New 25 x 50 Salt Generated Pool, no maintenance and much easier on the eyes! 3 Minutes to Private Beach! Free Parking, NO Beach Passes needed! This 4 bedroom, 2 bath home is nestled on 1.5 acres which abuts a 10 acre...
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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    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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    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    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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    • Hot Tub
    • Patio
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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! Lush gardens with landscape lighting, i...
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    11968, Southampton, Hamptons
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your private Southampton retreat awaits at this charming home nestled in a lush, tree-lined garden. This 3-bed, 3-bath vacation rental is well-appointed with sleeping arrangements for 9, a private gunite pool, and an ornately designed landscape. As you lounge in this pristine, stylishly decorated,...
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    11968, Southampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    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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    Location Information
    11946, Hampton Bays, Southampton
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 14
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Housekeeping Included
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful and private, six-bedroom, four-bath estate surrounded by a walkable 600-acre nature preserve on park-like grounds in Southampton. House is located steps to water (300 feet), bike ride along scenic roadway to private bay sunsets and only 4 miles from the world-class ocean beaches of...
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    11968, Southampton, Hamptons
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
    7 Bedrooms, 1 Bathroom, Sleeps 16 Quick View
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    • Internet Access
    • DVD Player
    • Private Outdoor Pool (Heated)
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    • Hot Tub
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A dream within reach. This unique home offers the best in indoor/outdoor living. The cathedral ceilings and interior with incredible finishes flow seamlessly into distinctive gardens on an acre of beautifully landscaped grounds. The new Olympic sized luxurious heated swimming pool and 7 person hot...
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    Location Information
    11946, Hampton Bays, Southampton
    Holiday Rental House - 7 Bedrooms, 1 Bathroom, Sleeps 16
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    This cozy cottage provides all you need to enjoy your summer vacation in the Hamptons. Inviting open living area with two bedrooms downstairs and two upstairs. The beautifully renovated kitchen has excellent cabinet and counter space for meal prep, but outside is where you will want to eat every...
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    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Secure Parking
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront: Architectural Gem in Water Mill / The Hamptons Enjoy our stunning home directly on prestigious Mecox Bay in Water Mill. This is a new listing. Exclusive property: A very private and luxurious compound with celebrity neighbors, fantastic views, heated Gunite swimming pool, outdoor...
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    Location Information
    11976, Water Mill, Southampton
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Summer in this fully renovated family home, rich with Hamptons history, on a quiet cul-de-sac. This 3-bed, 3-bath home with sparkling full-sized pool was the first on the block, and still sits on 1 full acre of land. 1.1 miles from quaint downtown Southampton where you can enjoy morning espresso,...
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    11968, Water Mill, Southampton
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Patio
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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 bay rights with easy access to sandy shores, this New York property is poetry in motion! -- THE PROPERTY --...
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    Location Information
    11946, Hampton Bays, Southampton
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
    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
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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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    11946, Hampton Bays, Southampton
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Be amongst the first to rent this newly renovated home where beach chic interior meets a woodsy style retreat. The home is ideally located just a quick 15 minutes to the villages of Southampton, Bridgehampton and 15-20 minutes to Sag Harbor and nearby beaches. Sitting on a full acre and nestled...
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    Location Information
    11968, Water Mill, Southampton
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Simple and clean house with all you need for a pleasant time.Lovely community right on the water, private beach just steps away. Deck and out door dining overlooking the pool and waters beyond. Large second floor with king bedroom and bathroom. Second bedroom with bathroom also on second floor....
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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • 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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    11968, Southampton, Hamptons
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is the perfect family getaway for you Summer vacation! July 1 - July 31 Special - Only $25,000! This home has panoramic views of the bay, with gorgeous sunsets! Beautifully renovated 2 story contemporary, with 4 bedrooms and 4 full baths. Only a 2 minute car ride, 22 minute walk to the...
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    Location Information
    11946, Hampton Bays, Southampton
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    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
    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    4 Bedrooms, 10 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Patio
    • Children's Pool
    • Wi-Fi
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    • 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
    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 10 Bathrooms, Sleeps 8
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Fabulous waterfront community with community private beach and tennis courts. Bedroom in lower level of home. with Queen bed. Adjacent sitting area with couch and TV. Separate entrance if desired, or come through the main ho.use. Feel free to take a dip in the pool and relax in the patio area....
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    11968, Southampton, Hamptons
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Luxurious amenities and an unbeatable location are only a few highlights of this 6-bedroom, 4.5-bath Southampton home! This well-appointed vacation rental invites guests to spend days barbecuing beside the private pool. When you're not sunbathing near the spacious pool house or relaxing in the...
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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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