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Rentals with Pool in Long Island, NY

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    $575
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    Hampton Bays
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    East Quogue
    6 Bedrooms / 5 Bathrooms / Sleeps 12
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    East Hampton
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    East Hampton
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Large Home which is walking distance to a gated beach (pass included with rental). Home is a 10 minute drive to all the Hampton Beaches and beautiful East Hampton stores. Great place to visit galleries, catch a show at the famous Guild Hall. Sag Harbor is a short drive away. Close to many Long... View all property information
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    1 / 17
    Cherry Grove
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Long season in 2 bedroom unit in oceanfront house. Come join us in our fabulous get-a-way from the hustle and bustle of everyday life. This incredible 'gay' oceanfront property is nestled in Cherry Grove, Long Island which hosts beautiful white sandy beaches. Sleep to the ocean waves by night and... View all property information
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    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    About this property
    Large Hamptons Beach House located in Quogue, NY. Features all new kitchen with quartz countertops, wine refrigerator, large American-style Fridge/freezer. two dishwashers, two sinks, bar, barstools, farmstyle table seats 10, flat screen tvs, wifi, beautiful porch. Adjoining cottage features LR,... View all property information
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    East Quogue
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Contemporary with major renovations in 2013. Open and bright, with great room and fireplace, expansive decks open out from bedrooms and from kitchen and living room. Heated swimming pool and Har Tru Tennis Court. Home is all on one level, and the pool has a child safety fence. The house has an... View all property information
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    $725
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    East Quogue
    4 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    Four Bed, four bath. Great for two families. + .Nice pool, basketball hoop, bikes, bogie boards, beach chairs, croquet, badmition, x box in basement, pool table, outdoor speakers, nice bar b que, great lounges by pool, big back deck close to Southampton beaches, close in hamptons. August 9th... View all property information
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    $333
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    1 / 35
    5 of 5 stars (1) Excellent
    East Hampton
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    About this property
    Enjoy privacy and peace on a beautiful Northwest Woods parcel with various outdoor entertaining spaces, including large deck with pool. Private 5 bedroom 2700sq foot house. Historic architecture, modern interior design mixed with the landscape's natural beauty provide living at its finest. This... View all property information
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    East Hampton
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    About this property
    Please contact us for availability. We do not use the Flipkey online calendar to manage reservations. Be the first to enjoy this completely renovated home. Summer 2015 reservations being taking now for a newly renovated East Hampton, 3 bedroom and 2 bath contemporary/modern loft home nestled on... View all property information
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    1 / 17
    Cherry Grove
    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    Come join us in our fabulous get-a-way from the hustle and bustle of everyday life. This incredible 'gay' oceanfront property is nestled in Cherry Grove, Long Island which hosts beautiful white sandy beaches. Sleep to the ocean waves by night and swim in our heated pool by day. Oversized modern... View all property information
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    $249
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    1 / 14
    5 of 5 stars (2) Excellent
    Greenport
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Overview: Waterfront Water's Edge luxury suite, Suite C-204, accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. Quoted rental rates include all taxes. Details: Offered by... View all property information
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    5 of 5 stars Reviewed September 17, 2014
    My friends and I really enjoyed our stay here. VERY clean, comfortable and the location was perfect for our visits to the local wineries. The private beach was very clean and we...
    5 of 5 stars Reviewed August 8, 2014
    Terrific Two bedroom condo on the water. Was there for July 4th, tons to do. Minutes from shelter island and views to die for.
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    5 of 5 stars (9) Excellent
    East Hampton
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This well-designed contemporary beach house with three bedrooms and two baths sits on an acre of blissful privacy. This vacation rental is located in East Hampton NW woods, 4 miles from East Hampton Village and 1.5 miles from Sammy's Beach. Close enough to it all, yet removed enough to feel like... View all property information
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    5 of 5 stars Reviewed August 26, 2014
    A fab house and fabulous pool and deck area, in a lovely location. This is the perfect base for a family or friends wishing to explore The Hamptons. We were visiting from the UK...
    5 of 5 stars Reviewed August 13, 2014
    I recently stayed here with a group of friends, and we all loved it. The house is well-kept, clean, and exactly like the pictures. We had everything we needed, and Patricia was...
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    4 of 5 stars (1) Very good
    Peconic
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • x
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    • x
    About this property
    A 4 bedroom home, located in Peconic, steps from a private, white sand Bay beach. Relax with long walks on serene beach, fish, bike, tour wineries, enjoy the bounty of land and sea, and unwind in your quiet surroundings. Our house is a large, comfortable, family-equipped 4 bedroom, 3 bath ranch... View all property information
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    4 of 5 stars Reviewed November 20, 2014
    Rented the house for the weekend. Miles from wineries and near by towns. House was very spacious, one hallway of 3 bedrooms. It was nice that the bedrooms were away from the...
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    $550
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    East Hampton
    6 Bedrooms / 4 Bathrooms / Sleeps 14
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    • ?
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    About this property
    6 bedroom, 4 bathroom Contemporary. Open floor plan, soaring ceilings; brand new kitchen and dining area. Pool, outdoor shower, hot tub. 5 minutes to beach, village, 7 minutes to Sag Harbor Village. Also available for holidays and special occasions short term. View all property information
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    $3,731
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    5 of 5 stars (1) Excellent
    Southampton
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    LOCATED IN THE VILLAGE PROPER- VERY WALKABLE LOCATION- ******LUXURY AT A BUDGET*****1.5 MILE TO COOPERS BEACH. A NICE SIZE COTTAGE YOU WILL NOT FEEL CRAMPED. It has a lovely flow for entertainment with multiple seating areas. Living area, fireplace area, dining area. Eat in kitchen and a large... View all property information
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    5 of 5 stars Reviewed June 29, 2014
    The house is in a beautiful area that is convenient to everything. I felt safe and comfortable, had a very relaxing experience staying there- and the home owner couldn't be...
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    $500
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    Hampton Bays
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    • x
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    • x
    About this property
    Immaculate four bedrooms, three full baths sleeps 8-10. Full gym, pool and jacuzzi nestled away in prestigious Red Cedar Ridge. Wi-fi internet and premium channels cable tv. Pool table, basketball and children play ground for entertainment. Five min drive to bay beach, fifteen min to ocean beach... View all property information
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    $700
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    Hampton Bays
    4 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    Great location with incredible views of the Tiana and Shinnecock Bay. Waterfront, boat dock, boat ramp, heated pool, fishing - right in your back yard! Spacious home with en-suite bathrooms in all bedrooms. Walking distance to shopping, transportation. Location, location, location !! The house is... View all property information
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    1 / 10
    Bridgehampton
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    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... View all property information
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    1 / 34
    East Hampton
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • x
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    About this property
    Spacious East Hampton vacation home features four large, furnished bedrooms with oversized master and walk-in closet, three full bathrooms with modern hotel finishes, large custom kitchen with stainless steel and paneled appliances, sunny family/living room with working fireplace, wireless... View all property information
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    $245
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    Montauk
    1 Bedroom / 2 Bathrooms / Sleeps 6
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    About this property
    It is a 1000 sq foot cottage which is private, surrounded by hedges with the master suite, kitchen, main room and decks all over looking the ocean. Very warm and cozy, with wood beam ceilings, modern kitchen with all new appliances including dish washer, and washer and dryer. View all property information
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    $50,000
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    1 / 18
    Sag Harbor
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    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... View all property information
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    East Quogue
    4 Bedrooms / 2 Bathrooms / Sleeps 10
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    About this property
    This 4 bedroom, 2 bathroom contemporary is just steps away from a private beach and marina. Some amenities include: New granite kitchen Cathedral great room with flat screen tv Hardwood floors Multi level decking In ground heated pool Patio furniture and gas grill Linens One car garage View all property information
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    $1,750
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    1 / 11
    Southampton
    6 Bedrooms / 4 Bathrooms / Sleeps 12
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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
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    1 / 52
    Southampton
    6 Bedrooms / 7 Bathrooms / Sleeps 14
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    About this property
    25 year age limit...please don't inquire if you do not meet the age requirements, you will be wasting your time and ours. This luxurious Southampton estate is set on a large private plot of land. With close proximity to Southampton village and world famous Coopers beach, the location of this... View all property information
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    1 / 25
    Southampton
    6 Bedrooms / 5 Bathrooms / Sleeps 12
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    • x
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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
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    1 / 4
    Sag Harbor
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • x
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    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... View all property information
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    $250
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    1 / 6
    Fire Island Pines
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Ocean Views
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    About this property
    Just 90 minutes from Manhattan, but worlds away from NYC! In the Fire Island Pines, an idyllic gay community (but friendly to all) on the beach with no cars, just the deer roaming wild. The cabana is small but very self contained. BBQ on the deck overlooking the ocean. 5 minutes walk to 'town'... View all property information
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    1 / 27
    5 of 5 stars (4) Excellent
    Sag Harbor
    5 Bedrooms / 8 Bathrooms / Sleeps 10
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    About this property
    This property is only for the very discerning renter. It is a designer's own home. Please read rental rates before inquiring. Minimum rental is one month during High Season unless you see an availability between rentals. During the off season 2 week rentals may be possible. This elegant 6000... View all property information
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    $900
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    Sag Harbor
    4 Bedrooms / 3 Bathrooms / Sleeps 6
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    • x
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    • x
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    About this property
    Walk in to the view of the sky and bay through the living room. The master suite is its own floor. the house is modern, there are three other bedrooms. Perfect home for a summer vacation. A short ride to Main Street, Sag Harbor, short walk to bay beach. View all property information
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    Southampton
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
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    • x
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    • x
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    About this property
    Enjoy the Hamptons! in this mint condition beautifully decorated and full equipped beach house. Located in Southampton, close to the Village and Beaches, this 4 BR open floor plan cedar shingle home is on almost 1 gorgeous acre on the border of a preserve with total privacy. Enjoy a first floor... View all property information
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    Bridgehampton
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    This spectacularly located house in Bridgehampton is perfect for anyone looking to escape to a lap of luxury. 2100 sqft, 2 story, 3 bedroom house in Bridgehampton on Old Sag Harbor Road with central air-conditioning, heated pool, 3 bathrooms, BBQ, WiFi, fireplace, central air, stainless steel... View all property information
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    East Hampton
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
    • ?
    • x
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    About this property
    Secure, Private Home on an Estate Lot, over 1/4 mile from nearest Roads. Heated Pool Barn Style Home. Great for entertaining with large patios and multiple outside dining areas. Rates LD toMD $ 60,000 July $ 25,000 August $ 35,000 July to LD $ 50,000 Extended LD to September 30, 2015 $ 10,000... View all property information
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    Amagansett
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    traveler have booked this property
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    • Pets allowed
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    • Suitable for children
    • x
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    • x
    About this property
    Great Hamptons style in Amagansett's Bell Estate. Less than two miles to ocean beaches and one mile from the bay, close to town, has every amenity and plenty of style. Overlooks a 60-foot heated gunite pool. Details include marble baths, wide plank Walnut flooring, cathedral ceilings, sound system,... View all property information
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    1 / 22
    Bridgehampton
    4 Bedrooms / 4 Bathrooms / Sleeps 9
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
    About this property
    Great house set on 2 acres and surrounded by 40 acres of reserve on 3 sides for complete privacy. Two masters with kings, two additional bedrooms and a den offer room for additional guests. The 500 square foot great room has soaring ceilings/ gas fireplace with multiple decks and balconies. Open... View all property information
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    1 / 32
    Sag Harbor
    7 Bedrooms / 5 Bathrooms / Sleeps 14
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    About this property
    25 year age limit...please don't inquire if you do not meet the age requirements, you will be wasting your time and ours. Drive through private gates to this secluded property with 7 over sized bedrooms; 5 baths. The house is an architect's resort-inspired vacation home. The property sits on a 2+... View all property information
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    Hampton Bays
    6 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Air Conditioning
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    • Private Fishing...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
    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... View all property information
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    East Hampton
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • x
    About this property
    Enjoy the Hamptons in the Fall, Winter and Spring in this renovated Contemporary within walking distance of the bay. The home features a large gourmet kitchen, spacious living room and dining room leading out to a private yard with new gunite pool, hot tub, indoor & outdoor grill and playground.... View all property information
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    1 / 22
    5 of 5 stars (5) Excellent
    Montauk
    6 Bedrooms / 4 Bathrooms / Sleeps 14
    travelers have booked this property
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    • Safe
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Elder access
    • x
    About this property
    *** Please see Summer 2015 (May - October) availability, minimum stay requirements and pricing information at the end of this listing before contacting *** Thinking of spending time in Montauk? Great idea! Enjoy all the East End has to offer from the comfort of a huge, newly renovated 6BR house... View all property information
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    5 of 5 stars Reviewed December 6, 2014
    We rented this house for a week because our son was being married in Montauk. It was perfect for our needs. We were able to accommodate extended family members with enough space...
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    East Quogue
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
    About this property
    Contemporary home on an acre of wooded land. Amenities include central air-conditioning and heat, wood-burning fireplace, heated in-ground pool, fenced-in backyard, sunroom. Located near local and high-end shopping and dining, farm stands, beaches, wildlife reserve, hiking, and outdoor activities... View all property information
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    1 / 28
    Hampton Bays
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Gym
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    Large swimming pool (43' x 22' free form), private and clean house in the woods with a 10 people outdoor jacuzzi. Complete equipped kitchen, walking distance to the bay and 5 minutes drive to town or the ocean. House inside indulge formal foyer, living room,TV room, work out area, office space... View all property information
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    5 of 5 stars (3) Excellent
    Long Beach
    5 Bedrooms / 4 Bathrooms / Sleeps 11
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    • Air Conditioning
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    • Pool Table
    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • ?
    About this property
    Large luxury air conditioned home located on Reynolds channel. Fish off the dock ,bring your boat and moor it in the yard or just enjoy the heated pool, short walk to town and beach. Take the train into NYC in less than an hour. Indoor and outdoor fireplace. 4 bedrooms and 3 bathrooms on the... View all property information
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    5 of 5 stars Reviewed February 25, 2015
    We saw the house before we rented so there were no surprises except the extra little items provided. Our family has rented often before and items like condiments, towels, bed...
    5 of 5 stars Reviewed July 15, 2014
    What a beautiful home and how amazing Debbie is! She stayed around to give us a tour of the house which I am glad she did because there was so much to offer. She really made this...
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    5 of 5 stars (1) Excellent
    East Hampton
    5 Bedrooms / 3 Bathrooms / Sleeps 11
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    This beautiful summer home sits on an acre property only 3 years old and newly painted and furnished by Perter Andrews. It has a salt water heated pool, new cedar children's jungle gym with swing set, elevated ceder deck, dining room that seats 10, Eat-in kitchen that seats 8, fireplace with... View all property information
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    5 of 5 stars Reviewed July 11, 2014
    I stayed last year with my husband, two kids and nanny for two weeks. We had not seen the house before we booked it and we were pleasantly surprised at how beautiful it was with...
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    East Hampton
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    • x
    About this property
    Newly renovated contemporary home sits on 1 acre up on a hill across the street from rolling fields at the edge of the Village. The open layout of the home affords large living space complete with a great room with wood burning fireplace, an open kitchen and dining area. On the bottom level, 3... View all property information
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    5 of 5 stars (1) Excellent
    East Hampton
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Shared Outdoor Pool...
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    • Pets allowed
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    • Suitable for children
    • x
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    • x
    About this property
    4 bedroom/2 Bath Single Level House with Central Air-Conditioning, located in the beautiful Clearwater Beach community. Rental includes electronic pass to private gated bay beach 2 minutes away. 7 minutes to East Hampton town and 9 minutes to ocean beaches.(East Hampton Main Beach or Amagansett... View all property information
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    5 of 5 stars Reviewed February 3, 2015
    Our family (2 kids, 2 parents, 4 grandparents) have spent our summer holiday here for the past 3 summers and are looking forward to our stay this coming summer. The house is...
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    Sagaponack
    6 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    • x
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    About this property
    With the ultimate prime Hamptons location, and the comforts of home, this vacation rental is an excellent value for all types of friends and family retreats. The outdoor areas are newly designed and rebuilt with 3,100 square feet of mahogany decking. Right outside the great room there is a new... View all property information
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    Quogue
    5 Bedrooms / 6 Bathrooms / Sleeps 12
    traveler have booked this property
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    • Washer
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    • Suitable for children
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    About this property
    4 upstairs bedrooms [ 2 Queen, 1 double (full), 1 single (twin)], 4 bathrooms [1 full, 3 showers, 2 of which en suite], attractive sitting room with 3 double full length glass doors giving onto a wide porch on two sides, separate dining room, fully equipped kitchen with modern appliances plus... View all property information
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    Water Mill
    7 Bedrooms / 7 Bathrooms / Sleeps 10
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    • ?
    • x
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    • ?
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    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... View all property information
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    Water Mill
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Pets allowed
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    • ?
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    • ?
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    About this property
    Four bedroom 4000sf house on 8.8 acres of gorgeous, park like property, with 3 acre private pond/lake, and free form gunite pool,right in the heart of Watermill/Southampton. !0 blocks off of Montauk Hwy, 4 minutes to ocean, 5 mins to town of Southampton. Fantastic location! Also has central air,... View all property information
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    Lido Beach
    5 Bedrooms / 3 Bathrooms / Sleeps 11
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    • Air Conditioning
    • Balcony
    • Children's Pool
    • Dishwasher
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    • Internet Access
    • Ping Pong Table
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    About this property
    PLEASE SEE HOMEAWAY (LISTING # 323667) AND VRBO FOR OUR 18 5STAR REVIEWS!!! We allow up to 1 more visitor for a total of '12' for additional rental charges. After an 8 year continuous, home renovation, a group of up to 12 can experience this remarkable 3,000 square foot perfectly situated... View all property information
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