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Holiday Rentals with Pools in Sagaponack

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    Don't let other travellers get your favourite Sagaponack area holiday rental. You're so close to securing your perfect getaway. Book today.
    33 Matching Rentals in the Sagaponack AreaView all 63 rentals
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    Sagaponack
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Sagaponack
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    The following rentals are within 10 kilometres of Sagaponack.
    Elegant Designer Hamptons Retreat in Sag Harbor1 / 28
    (5)Excellent
    Sag Harbor
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Sag Harbor
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Washer
    • Satellite TV
    • Grill
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located a few blocks from Wollfer Vineyard and blocks away from the town of Sag Harbor. You will have all the privacy you want. Enjoy a beautiful built in pool. The home is clean, stylishly decorated, and close to gorgeous beaches. Work out room, everything! The location...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Sag Harbor
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Put up your feet and relax in this idyllic home just minutes from Long Beach and the rest of the luxuries the Hamptons have to offer. The open concept kitchen is a chef's dream, with a six burner Viking stove, Subzero refrigerator, Bosch dishwasher, and plenty counter space; perfect for...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Chic and Modern Beach retreat with heated Pool1 / 16
    (1)Excellent
    Sag Harbor
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Washer
    • Wi-Fi
    • Balcony
    • Grill
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2016
    This house has everything you need and is perfectly located. It is not far from Sag Harbour in a quiet area. Close to marina for kayaking and stand up paddle boarding. With...
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    About this property
    Privately situated on a park-like landscaped grounds, this classic 2 story French cottage was completely renovated for modern comfort and indoor/outdoor summer entertainment. This delightful house features an open-plan living room with fireplace, dining room, a gourmet kitchen with stainless...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Sag Harbor
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 & Jacuzzi. The home is clean, stylishly decorated, and steps away from a gorgeous north Sea bay beach. Visit Southampton or Sag Harbor town only 3 min...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Spacious Home with Pool in Heart of the Hamptons!1 / 33
    (2)Excellent
    Water Mill
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Grill
    • Patio
    • DVD Player
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2016
    All I can say is WOW! Patrick's home is a dream!! Patrick has done an amazing job decorating this home. It was so comfortable inside and out from tasteful furnishings, a...
    Reviewed 19 July 2016
    This has it all, in a Perfect location, convenient to Hamptons shopping, beaches, restaurants, with the quiet of a private retreat. The house has large open rooms for...
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    About this property
    This beautiful home is in a great location, was just renovated and is luxuriously furnished and thoughtfully appointed (including original art, and luxury linens, kitchenware and dishes new for 2016). Perfect for relaxation and entertaining, highlights include: -Large open concept family room...
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    Water Mill, Hamptons 11976
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Water Mill
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Internet Access
    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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    Water Mill, Hamptons 11976
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Bridgehampton
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious, renovated 5-bedroom, 4-bath home is on a secluded 1/2 acre, with a 200-foot private driveway leading to the wonderful, bright residence. The house backs onto a community reserve, so there is complete privacy in the pool, decks, and backyard. On the main level, there are 4 bedrooms...
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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Bridgehampton
    11 Bedrooms, 9 Bathrooms, Sleeps 22 Quick View
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    Amenities & Details
    • DVD Player
    • Sauna
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Wi-Fi
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A total of 15,000 sq.ft. encompasses 11 bedrooms and 11.5 bathrooms including the main house and a luxurious guest house both with three floors of superbly crafted living space. Amenities include all-weather tennis, an over sized 25' x 55' heated gunite pool, fully finished lower levels in both...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 11 Bedrooms, 9 Bathrooms, Sleeps 22
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    Water Mill
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Water Mill, Hamptons 11976
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sag Harbor
    10 Bedrooms, 13 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spectacular 13,000 square foot estate, on 30 acres of open reserve with water views, boasts 11 bedrooms, 13 full bathroom, heated gunite pool, large outside patio area, Grill, perfect for entertaining, weddings, large family gatherings, etc. Located in Bridgehampton neighborhood in Sag Harbor....
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 10 Bedrooms, 13 Bathrooms, Sleeps 16
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    Wainscott
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Washer
    • Patio
    • Porch
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are a family of 4. My kids love that I made a tv/playroom next to my kitchen separated from our own TV in the open kitchen/living room space. This house is located in the Best area in the Hamptons. 5 minutes drive from Sag Harbor Main Street, 7 minutes drive to East Hampton Main Street, 15...
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    Wainscott, Hamptons 11975
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Water Mill
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Garden
    • Satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    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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    Water Mill, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Water Mill
    7 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Sauna
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Washer
    • 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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    Water Mill, Hamptons 11976
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 10
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    Sag Harbor designer home, Chef's kitchen & one block from the water1 / 14
    (1)Excellent
    Sag Harbor
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 March 2017
    Our family enjoyed a great week in Sag Harbor and wonderful accommodations. The house is as advertised, nicely and warmly decorated with beautiful pool and outdoor grounds. The...
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    About this property
    For a truly authentic experience of Sag Harbor, stay at this delightful 5-bedroom, 2-bathroom designer's home with oversized heated pool and ideally situated just 2 blocks from Long Beach . With 2,800-square feet of living space and enough sleeping accommodations for up to 10 guests, this residence...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Sag Harbor
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy 2 acre beautiful parcel adjacent to hundreds of acres of town reserve sits this updated light filled home with sweeping lawn, and reserves on 3 sides for complete privacy. Spacious with 4 bedrooms and 3.5 baths,Two masters with king beds and private baths, two additional bedrooms one...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Bridgehampton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful contemporary home set on 1.6 private idyllic acres. Walk to town, near beaches. Easy drive to Sag Harbor, Southampton and East Hampton. Right by Hampton Classic and Polo grounds. New designer furnishings and linens. Separate master suite with Jacuzzi and steam shower. 3 Additional...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Designer Decorated 3 Bedroom in Prime Location Heated Salt Water Pool1 / 21
    (3)Excellent
    Bridgehampton
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2017
    Very clean, very nice. The description is very accurate. Everything was just like the pictures! AC and heat worked well. Great water pressure. Location was perfect, very...
    Reviewed 7 March 2017
    On a quiet street, in a perfect location. My family stayed here for presidents weekend. We loved the modern look of the house and it had everything we needed. The house is...
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    About this property
    Bridgehampton White House RATES INCLUDE THE FOLLOWING: Electric consumption, cable TV & wi-fi, propane consumption, telephone, trash removal, lawn & pool service and heating of pool to 85 degrees between Memorial Day and Labor Day. OVERVIEW OF HOME: 3 bedrooms 3 bathrooms Finished Basement with TV...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sag Harbor
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Grill
    • Patio
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The feeling of Zen surrounds you as you enter upon this European designer's hideaway..Custom appointments of quality and luxury fill this Hampton's home. Located 12 minutes walk to Main Street of the prestigious Sag Harbor Village....0.4 acres of beautifully manicured totally private lawns with...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Sag Harbor
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning, spacious three bedroom home, with water views from every room, and a heated gunite pool, will be your dream-come-true vacation rental. You will be minutes away from several gorgeous beaches as well as 1 mile from the lively and historic village of Sag Harbor. Decorated to a high...
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    Location Information
    Sag Harbor, Hamptons 11963
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sag Harbor
    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Outdoor Dining Area
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    • Shared Garden
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the quaint historic whaling Village of Sag Harbor, 12 minute walking distance to the center of town, with close proximity to the bay and ocean beaches. This European designer's home totals 5000 sq.ft., the lower level just shy of 1000, sq ft and is the designer's private lower level...
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    Sag Harbor, Hamptons 11963
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 8
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    Sag Harbor
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This villa features 5,600 +/- sq. ft. of living space with five bedrooms, four and one-half baths, plus a gourmet kitchen, living room with fireplace, media room, office, large master, and a finished lower level, on 1.87 +/- beautifully landscaped ac. Located in The Hamptons neighborhood in Sag...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Sag Harbor
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy acre beautiful parcel sits this updated light filled home in a Development with wide street for walking. With 4 Master Ensuite bedrooms, spacious with 2 masters with king beds and private baths, one with queen bed and private baths and the other with two twin beds and private bath...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Wainscott
    7 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous estate in a completely secluded, wooded area of East Hampton. Owner lives in LA. Rooms are luxurious with modern decor. Great backyard swimming pool. New hot tub being installed. Home designed by famous architect Robert Strada. Artwork and furnishings extra. Great year round home.
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    Wainscott, Hamptons 11937
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 10
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    Bridgehampton
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Satellite TV
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home features four bedrooms and four baths, and fantastic chef's kitchen, and large bright living spaces. The guesthouse includes two additional bedrooms and a bath. Expansive open lawns and a heated gunite pool complete the property. This south of the highway, shingled masterpiece is close to the...
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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Wainscott
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Delightful family house in quiet neighborhood. Just minutes to the ocean and the charming hamlet of Wainscott; central to all in the Hamptons! Open floor plan features a (eat-in!) kitchen, dining area and living room. There is a separate den for privacy. Amenities include four bedrooms and three...
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    Location Information
    Wainscott, Hamptons 11975
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Water Mill
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 grill with Party bar,...
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    Water Mill, Hamptons 11976
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Bridgehampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely 4 bedroom home backs to preserve and is located just north of the village with an open floor plan and wonderful light and high ceilings throughout. Main floor has guest bedroom and bath, living room with fireplace and double height ceilings, separate dining area and eat-in kitchen, which...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sag Harbor
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Garden
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Village traditional on a quiet village street perfect for family gatherings. Magnificent backyard including a stone patio with fridge, grill, heated gunite pool and beautiful gardens. The park is accessible from our backyard allowing children to enjoy fields and playground and adults to have...
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Sag Harbor
    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Spacious Contemporary home is great for entertaining and play. The interior kitchen/dining is open and light filled. There are 2 living rooms and 2 dining areas as well as a breakfast bar. There are sliding glass doors to the large deck which affords flow between interior and exterior....
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    Sag Harbor, Hamptons 11963
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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    Bridgehampton
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Parking
    • Private Garden
    • Satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely home on prime BH North Street, with privacy and lots to do around. Gourmet kitchen with good knives and all clad. Garden is organic with lots of herbs and flowers. There are 3 whirlpool baths. One king. Size bed is sleep number. Owners want you to enjoy!
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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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