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Long Island Family & Kid Friendly Rentals

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    Travelers to Long Island are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    435 Matching Rentals in Long IslandView all 500 rentals
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    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Waterfront Hamptons Beach House w/ Dock, Hot Tub, & Awesome Views, Walk to Beach1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    North Fork 5 bed room home with forever farm view1 / 37
    (10)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Secure Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 7, 2018
    Outdoor furniture was a mess could not sit on it. King master bed mattress was terrible you sunk in the middle of it very hard to get on the bed it was so high and no step stool...
    Reviewed August 11, 2017
    This is a really cute house with a lot of bedrooms. The common areas are cozy but the backyard had plenty of room for a large group (10 people) to hang out and play yard games...
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    About this property
    Five bedroom home with central air conditioning.This home has modern kitchen pillow top bed a large 52' plasma tvs.This home has tv in master and queen br bbq grill,12 gazebo with a tumbled stone patio.The patio has a table with seating for eight The view from the gazebo area is about one mile...
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    Aquebogue, Riverhead 11931
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Beautiful French Country Cottage1 / 23
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Wi-Fi
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 7, 2018
    If you love the North Fork you will absolutely love staying here. This cottage embodies everything that I wanted for my time spent here which happened to also be my birthday...
    Reviewed March 13, 2018
    My family of four stayed in one of these twin cottages. They are mirror images of each other with separate entrances and patios. Plenty of parking right outside and just...
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    About this property
    Welcome to the Victorian Seasons guest cottages, nestled between wildlife preserves and protected land. Victorian Seasons is a significantly important historic site that dates back to 1855. It is on the historic corridor in the heart of East Marion on the beautiful North Fork of Long Island....
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    East Marion, North Fork 11939
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Victorian Seasons one bedroom duplex farmhouse1 / 28
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • DVD Player
    • Terrace
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2018
    Beautiful fully appointed, clean, antiques unit that had everything we needed for a two-day getaway. Close to good restaurants (in Greenport) and beautiful beaches and parks...
    Reviewed July 5, 2018
    Had a wonderful time .beautiful landscape views . Accommodating and Friendly Staff it was such a lovely stay
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    About this property
    Victorian Seasons is a unique historic property. All work is of excellent craftsmanship and is historically accurate in restorations. This one bedroom apartment features a kitchen with stove/oven, refrigerator and necessary utensils. The bathroom is new and designed to evoke the 1930's charm of...
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    East Marion, North Fork 11939
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Beech Tree Cottage1 / 15
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Shared Yard
    • Wi-Fi
    • Outdoor Dining Area
    • Parking
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 18, 2018
    With a full kitchen and living room, outdoor terrace and perfect so-close-you-can-walk-to-town setting, you will be so happy you snagged this spot! I’m picky, and I know what’s...
    Reviewed August 7, 2016
    Spent two nights at Beech Tree with my husband and grown son. Cottage is located within walking distance of town, in a nice residential neighborhood. Kitchen is well stocked, we...
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    About this property
    Beech Tree Cottage is a charming two-bedroom, one-bath guest cottage conveniently located in the historic district of Sag Harbor, NY - a 5-minute walk along the waterfront to Main Street and the center of the village. The beach is a short drive or bike ride away. The owners are full-time residents...
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    Sag Harbor, Hamptons 11963
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1st fl Parkview apt/private yard+wifi+parking incl1 / 33
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
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    • Cable/satellite TV
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 26, 2018
    Very roomy first-floor apt in 2-family home. Bright and airy, full kitchen. Ample bedroom space. Convenient to Western Nassau via parkways and NYC via LIRR. Ez is the perfect...
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    About this property
    Gorgeous Freshly remodeled 2 bedrooms/living room 1st floor Park View apartment. It comes with a Full bath (shower/tub combo) and a fully equipped kitchen (stove, fridge, microwave, toaster oven, pots/pans, dishware, glassware, silverware, and kitchen utensils). Its warm cozy feeling will make you...
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    Valley Stream, Long Island 11580
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Beach House In Wine Country; walk to beach, large sun room, outdoor dining1 / 16
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Porch
    • Grill
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 3, 2015
    An absolutely stunning and beautiful home. Clean, comfortable, fully updated, this house is perfect for peace and relaxation. The bright and spacious sun room is perfect for...
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    About this property
    Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide 2 comfortable...
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    Location Information
    Southold, North Fork 11971
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    North Fork House with Private Beach Access1 / 14
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Parking
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 5, 2018
    I just returned from the most fantastic vacation in this lovely home in a quiet neighborhood just outside of Greenport. We were 2 families with 3 children ranging from 9 - 11...
    Reviewed July 23, 2017
    We have been renting in the North Fork for 7 years and this was by far the best house ever. We stayed for 2 weeks in July and Jane, the owner, was super responsive with all...
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    About this property
    Contemporary 4 bedroom 3 bath house with private Long Island Sound beach access and community tennis and bocce courts in East Marion. Secluded lot with swing set. 2 adult bikes and 2 kids bikes, beach chairs and toys included. Cook's kitchen, large deck. 10 rooms total, including master bedroom...
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    Location Information
    East Marion, North Fork 10014
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cutchogue Beach Cottage1 / 18
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • Central Heating
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 23, 2016
    We had a very happy stay here. Contact with Julie was first class, the house is very tastefully decorated and comfortable. It is ideally situated to explore further but has...
    Reviewed August 8, 2016
    We so enjoyed our time here. You really can't find a more homey cottage and the close proximity to the great beach and scenic hilltop playground was tops. Julie was wonderful...
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    About this property
    Cozy Cutchogue Beach Cottage on the North Fork of Long Island. It has 2 bedrooms with queen sized beds and there is a sleeping loft appropriate for children over 9 years old (one queen sized bed and one twin). Deck and backyard with gas grill, outdoor picnic table, fire pit, and tire swing....
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    Cutchogue, North Fork 11935
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Luxury Hamptons Vacation Home w/NEW Pool, Tennis Court, Hot Tub1 / 32
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Patio
    • Wi-Fi
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS TURNKEY PROPERTY HAS SOME OF THE BEST AMENITIES IN THE HAMPTONS. MANY OF THE IMPROVEMENTS WERE COMPLETED IN THE LAST TWO YEARS! Compare us with other area properties: - FRESHLY PAINTED EXTERIOR IN 2017 - HOUSE IS FULLY UP TO CODE, INCLUDING EGRESS WINDOWS IN LOWER LEVEL BEDROOMS FOR YOUR...
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    Location Information
    Quogue, Hamptons 11727
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    'Pennies From Heaven'1 / 25
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 21, 2016
    House and groundsI stayed at this property with my boyfriend and another couple for a long weekend. It was great!! It was a super easy drive from the city and upon arrival, we...
    Reviewed June 12, 2016
    We had a terrific stay with our family at this prefect private get away that offers it all . Set on a private cul de sac for peace and quiet yet minutes from town, shopping...
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    About this property
    Summer house that has it all! This 4 BR/3 Bath newly updated property, sits on a 1/2 acre lot with a newly lined in-ground pool with Trex decking surround and features an open concept main living space, entertainment space, high end finishes and tons of privacy. Local Realtors have identified this...
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    Hampton Bays, Southampton 11946
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    PArkView Beauty/private parking+wifi included1 / 34
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2018
    This house is a lovely corner lot on a nice street with park. The house was well equipped, but bring beach towels. Really great is the nearby places which deliver. Would love to...
    Reviewed June 14, 2018
    Nicely furnished and well supplied 2-BR 1 bath walk-up with efficiency kitchen in two-family house centrally located on Long Isand's South Shore. Close to local shopping and NYC...
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    About this property
    Large Bright and freshly remodeled. The property is equipped with anything you can possibly imagine. A warm cozy feeling will make you feel at home. Super quite/cool/safe residential location surrounded by park. Steps to Valley Stream train station (Long Island Rail Road),...
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    Location Information
    Valley Stream, Long Island 11580
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Cozy Ranch1 / 28
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Yard
    • Secure Parking
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 21, 2018
    First of all Cristina is a wonderful host. We very much appriciate her warm welcome and generosity to use her entire house, including the full kitchen and all the contents of...
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    About this property
    This is a very cozy house with lots of trees around. Only 7 minute drive to the beach. The house has Two bedrooms, one queen bed in the master bedroom, a trundle bed in the second bedroom. Also a comfortable sofa bed in the living room. There is plenty of space in the backyard with a patio table...
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    East Quogue, Hamptons 11942
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Blue Parrot 3 Bedroom, 1 bath, large deck, wi-fi, sat TV, d/w, microwave1 / 33
    (3)Average
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Private Yard
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 2018
    While Ocean Beach has changed since I last visited, its for the better. This was just what I needed. The house is quiet yet central to everything. A nice walk to the...
    Reviewed August 13, 2018
    All in all a decent apartment. The owner expect you to clean and dry the sheets before check out (or pay 100$), which kind of ruins the 'check out' day. Not a big fan of wall to...
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    About this property
    Ocean Beach, Fire Island, NY Summer Rental. Steps from beautiful ocean beaches, shops, restaurants, night life, ferries and all the Capital City of Fire Island has to offer. Weekly Rental Only Please. (Ocean Beach Regulation) Credit Cards, Pay Pal, Zelle, Venmo...
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    Ocean Beach, Fire Island 11770
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Beautiful Classic North Fork Home, wrap around porch, pool, walk to beach1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Housekeeping Included
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2018
    Wow! Can’t say enough about this house. Stayed here with my girlfriend and her parents and we couldn’t have been happier. There is so much to do on the north fork but we chose...
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    About this property
    Walk to beach, wrap around porch, inground pool, jacuzzi, fire pit & much more North Fork Vida House Our just listed, circa 1987, traditional, classic home is situated on almost an acre of land in Southold NY, right in the middle of LI Wine Region and just 10 minutes from the village of Greenport...
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    Location Information
    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet and friendly neighborhood. Prime location, close to all. Beautiful room in a house in Hewlett. A few minutes walk to the LIRR Hewlett station and bus stops with connections to Brooklyn, Queens, Manhattan; just 15 minutes to JFK; 10 minutes drive to Long beach. Across the street from CVS...
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    Location Information
    Hewlett, Long Island 11557
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Unique  English Country Cottage1 / 22
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
    • Wi-Fi
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2018
    Very cute, clean, neat, comfortable cottage in a peaceful setting with beautifully manicured surroundings. Definitely coming back again!
    Reviewed August 12, 2016
    The house was beautifully maintained inside and out with a fantastic outdoor area to sit chill and enjoy barbecues and watch the local wildlife with a pretty rocky road beach a...
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    About this property
    . North Fork- East Marion- Charming unique twin cottages with cedar roof and historical significance. Each cottage is new and elegantly appointed. Wide plank flooring and knotty pine doors. Complete kitchen with granite counters and dishwasher. New bath with Italian tiles. Central air...
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    East Marion, North Fork 11939
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 15 Quick View
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    • Cable/satellite TV
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    6000 Sq Ft Ranch Estate with Over Sized and Spacious Dimensions 5 Bedroom 2.5 Bathrooms Frank Lloyd Wright Prairie Style Home 4 Acre Plot Borders a 2550 Acres Wild Life Refuge Japanese Inspired Decor and Architecture, Custom Built Home one of a Kind Hot Tubs Dinning Room Sun Room Great Room High...
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    Location Information
    Brookhaven, Long Island 11719
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 15
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    Hampton Bays, south of 27A1 / 26
    (14)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Outdoor Dining Area
    • Cable/satellite TV
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    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 5, 2018
    I stayed at this lovely house for my bachelorette party. Doug was an absolute pleasure to rent from. The house was gorgeous and fully equipped with everything my girlfriends and...
    Reviewed August 14, 2018
    The pictures really don't do this house justice. The floors are beautiful, the kitchen is great, the bedrooms are comfortable, and most importantly the house was VERY clean. The...
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    About this property
    Completely renovated 4 bedroom home on quiet street in Hampton Bays. In town location. Walk to shops and dining. 3.5 miles to Atlantic Ocean and 1.0 miles to Shinnecock Bay. Large property with lovely deck and furniture. Handicap accessible with bedroom and wet room on first floor. Deck...
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    Location Information
    Hampton Bays, Southampton 11946
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 12, 2018
    Spacious and well maintained home. Wonderful and responsive owner.Especially loved the lofted ceiling, great room, huge kitchen island, master suite with big walk-in closet and...
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    About this property
    ***PLEASE INQUIRE FIRST (EMAIL OWNER) BEFORE INSTANT BOOKING!!.. 631 - 365 - 3828 Located east of the canal on the beautiful Peconic Bay, over 100 feet of sandy beach, walk down the shore to for food, drinks and entertainment! Beautiful, crystal clear water, 5000 sq ft custom Waterfront “GREEN”...
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    Location Information
    Southampton, Hamptons 11946
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    'Amazing Summer Getaway In East Quogue'1 / 22
    (5)Excellent
    8 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
    • Central Heating
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 8, 2017
    The pictures shown don't do this house justice. This is a beautiful home and the host Sal was very helpful and accommodating. He answered any and all questions and even mailed...
    Reviewed May 23, 2017
    This homey 8-bedroom house is on a beautiful, quiet street, just a short drive from wineries, the beach, great restaurants with ocean views, and the town of South Hampton. I...
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    About this property
    Beautiful two level 4,100 sq. ft. home in East Quogue is sure to accommodate all your summer get away needs. If you enjoy spending quality time together our home provides a large backyard with an in-ground heated pool, and a new BBQ. Than come hang out inside in our game room that holds a...
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    Location Information
    East Quogue, Hamptons 11942
    Rental Home - 8 Bedrooms, 5 Bathrooms, Sleeps 8
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    Village Fringe glassy Modern with Pool and Tennis1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 24, 2017
    My family was looking for a quiet house to relax in a beautiful setting, and we had just this house. This sunny, bright, clean and pleasant...most of all, luxurious house with...
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    About this property
    SPECIALS: Please contact us for 2+ week early Bird specials. Peace and quiet awaits in this modern house on the village fringe, featuring a first floor master with walk in closet, wonderfull spa-style master bath, flatscreen TV and direct access to the pool and outdoor shower. The kitchen, the...
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    Location Information
    East Hampton, Hamptons 11937
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 bedroom Private Family Get Away1 / 45
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Children's Pool
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2018
    The kids loved the pool! beaches are only a few miles away. We needed a few items and were happy to know that their were a shopping mall right around the corner!
    Reviewed March 5, 2018
    Carrie was a wonderful host and left my crew some champagne and cookies for the weekend! We used the house for a bachelorette party in the Hamptons in August and It was perfect...
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    About this property
    Private, spacious 5 bedroom, 3 bath home w/yard for relaxing, entertaining & sports. In deck heated pool w/safety fence. Huge kitchen, premium cable, wi-fi, fireplace. Neighborhood ideal for families - long walks, bike rides, wildlife watching. Large great room with skylights includes open kitchen,...
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    Location Information
    Westhampton Beach, Hamptons 11978
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    The Farmhouse1 / 15
    (1)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Reviewed February 6, 2017
    My family rented this house for the holiday week between Christmas and New Years. The house is located within walking distance to town - which was quite great The house has...
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    About this property
    Renovated and tastefully furnished, The Farmhouse features one of the largest wrap around porches in the village and it is enviably located steps away from the town's best restaurants and bars, as well as just 3 short blocks to the beach. The space Just steps away from the center of the Greenport...
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    Greenport, North Fork 11944
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Victorian Seasons Stirling1 / 44
    (5)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed July 10, 2018
    I stayed here with two families for a weekend getaway and our jaws dropped when we saw this stunning property. Walking through the door felt like stepping back in time into the...
    Reviewed July 5, 2018
    Amazing stay at Victorian seasons and beautiful hospitality walking distance to Greenport village .. The grounds were breathtaking surrounded by beautiful gardens and amazing...
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    About this property
    Elegant and especially designed and built for one of the wealthiest bankers on the North Fork. Situated on enormous property in the most prestigious setting of the National Historic District in Greenport Village. Lovingly restored to its original elegance and authentic Classic Queen Anne...
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    Greenport, North Fork 11944
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    Elegant Designer Hamptons Retreat in Sag Harbor1 / 28
    (5)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    About this property
    Only for the very discerning renter. It is a designer's own home. Please read rental rates before inquiring. Minimum rental is 2 weeks during High Season unless you see an availability between rentals. During the off season 1 week rentals may be possible. This elegant 6000 square foot home...
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    Sag Harbor, Hamptons 11963
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    For a rejuvenating, fantastical getaway from the day-to-day doldrums, this gorgeous waterfront home is waiting at the very end of rustic Windward Road for you. With four main bedrooms, and a completely furnished attic that can serve as room for even more, you can bring your whole family for a...
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    Orient, North Fork 11957
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Adorable home with Large PRIVATE deck- Fire Island1 / 28
    (7)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed June 8, 2016
    Dennis was really helpful before with directions and how to get in the place.Everything was really clean and there were a ton of great things to help keep us like outdoor...
    Reviewed September 8, 2015
    I had never been to FI before, and neither had a bunch of my friends. We rented this house with not many expectations in mind but some beach time and needless to say, all of...
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    Our wonderful cottage comes with all the expected amenities for the total vacation experience. It has two decks, a large private rear deck and fun smaller front deck for people watchers . Fire Island boasts no private cars in the summer until Sept 15 so the kids have freedom to wander safely after...
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    Kismet, Fire Island 11706
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beach Cottage in Wine Country ,Walk To private bea1 / 20
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Porch
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    Pet friendly
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    Reviewed September 7, 2017
    Our stay and location exceed our expectations, from our daily walks to the beach with our 7 year old son, to buying farm fresh produce at the local farms. One would never assume...
    Reviewed September 27, 2015
    We had 4 great sunny days at Baiting Hollow.The cottage has a warm, cozy atmosphere (-> photos).The beach is gorgeous, just as perferct as you would wish for swimming...
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    About this property
    Adorable 2 bedroom cottage sleeps 4 1000 ft to private beach! All new paint Full kitchen. New bathroom Master BR w/ queen bed , a/c,ceiling fan ,flat screen TV . 2nd BR w/ 2 twin beds. Living room with a/c, flat screen TV with netflix. Wireless Internet. Living room opens to to large screened...
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    Baiting Hollow, Long Island 11933
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Luxury Hamptons Quogue Village 4BR Modernist Retre1 / 30
    (3)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Reviewed June 3, 2017
    We just found out about this and it's a wonderful property. The town of Quogue houses some of the most successful people inNew York and is astronomically expensive.The Quogue...
    Reviewed August 3, 2014
    I recently stayed at the Luxury Hamptons Quogue Village 4BR Modernist Retreat with my girlfriend, her sister's and brother in law, and had the best time. The house is new and...
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    About this property
    Quogue Village Modern 6BR, 4WC recently renovated in rustic modern style. Light and airy with skylights and large windows and doors. Huge chef's kitchen boasts 6 burner range and double sinks. Expansive 40 ft pool, 8 person hot tub, 1.3 acres on quiet wooded cul de sac, and Quogue Village beach...
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    Quogue, Hamptons 11959
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Southold, NY Beach Cottage, Walk to Beautiful Founders Landing Beach, Farm Stands, Wine, Shopping, Let us know your dates! BI - Weekly Rental - Bring the Dog(s) & Work Here! WIFI & CABLE Beautiful Restful Retreat! Come experience award-winning wineries, antique shops, art galleries, Summer 2017...
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    Southold, North Fork 11971
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    A Chef's Dream Kitchen1 / 29
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed August 18, 2014
    We stayed here with our two daughters who are ages 20 and 18, and all of us enjoyed this home! The location is quiet, and is close to the beaches and the main town. As seen in...
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    About this property
    Very stylishly renovated on .60 acre, this East Hampton property features central air, 3 bedrooms and 2 baths. Great room with fireplace and lots of sunlight. Skylights in kitchen and living room. Top of the line Sub-zero refrigerator and wine storage. A chef's dream kitchen with two ovens and...
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    East Hampton, Hamptons 11937
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    WATERFRONT BEACH HOUSE - SOUND BEACH1 / 34
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed August 2, 2017
    My family and I stayed at Shay's Beach House last week. We were pleased to find a cozy home with everything we needed as described. There were 4 adults, and 4 kids aged 6...
    Reviewed July 25, 2017
    I spend my vacation with my family of 4 people at "Waterfront Beach House - Sound Beach” and I assure that it’s everything you want it to be.The House is a dream and the...
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    About this property
    WATERFRONT BEACH HOUSE - SOUND BEACH - Long Island Located on the bluff with amazing views of the Long Island Sound around the year. 1:15 min drive (60 miles) from Manhattan. 25 min. from the Hampton crowd. Weather you're coming to visit family in the area, attending a wedding / event at...
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    Sound Beach, Long Island 11789
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    waterview house. rocky point. long island.New york1 / 33
    (7)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2016
    My wife and I were looking for a quiet peaceful getaway to relax. We found exactly what we were looking for in this rental. We had the option of a sparcely populated beach on...
    Reviewed September 24, 2015
    Patty is the nicest person you will ever meet. Her house is in pristine condition and is positioned at a short walk from the sparsely populated private beach. Very relaxing and...
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    About this property
    Quaint 3 bedroom, 1 bath home, with beautiful views of the long island sound, and Connecticut, from the kitchen, dining area, bedroom, and back yard.Heat and Central air conditioning, cable, internet, Netflix,phone. electric stove/oven, toaster, coffee maker,microwave,convection toaster oven,...
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    Rocky Point, Long Island 11778
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Westhampton Waterfront 6 Bedroom Secluded 3 Acre E1 / 13
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    About this property
    The Perfect Getaway Westhampton Waterfront Secluded Estate Drive along this Hamptons vacation rental properties private stonewalled 800 ft driveway and into what Hampton style living is all about. This home is located on three acres of beautiful waterfront property in Westhampton. With...
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    Westhampton, Hamptons 11977
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Quiet and friendly neighborhood. Prime location, close to all. Beautiful room in a house in Hewlett. A few minutes walk to the LIRR Hewlett station and bus stops with connections to Brooklyn, Queens, Manhattan; just 15 minutes to JFK; 10 minutes drive to Long beach. Across the street from CVS...
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    Hewlett, Long Island 11557
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    East Hampton Dream House 'Serendipity' - Great Buy1 / 7
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
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    Reviewed October 3, 2018
    My father and I stayed here for a week at the end of this past September. I can say without a doubt we will absolutely be booking another stay here in the future! Even though...
    Reviewed June 25, 2017
    My wife and I stayed at this lovely place last week. Our two sons and their girlfriends also stayed. We had a fantastic time. The heated swimming pool was absolutely fabulous...
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    About this property
    Enjoy this sophisticated, newly renovated, three-bedroom, three-bath contemporary on one of the premier lanes near Jackson Pollack's house in East Hampton. Twenty-four-hundred square feet with oak flooring throughout. Great light in the beautifully designer decorated double height living/dining...
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    East Hampton, Hamptons 11937
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    East Hampton Family Retreat with Cottage1 / 41
    (5)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 30, 2017
    Relaxing weekend. Leanne has very thoughtfully planned out the house, there are grills, gas fire pits, a roof decks. The furniture is very comfortable. The floor plan is great...
    Reviewed August 6, 2015
    The best vacation ever! The main house, the cottage, the pool, the kitchen, the cabana, everything met or exceeded our expectations. The kitchen was stocked with everything...
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    About this property
    2 night minimum weekends, 3 night minimum all holiday weekends. Hot tub and pool are closed for the winter season.. Hot tub closes Dec. 1st., 2018 Pool closes Oct. 1st. 2018 Please note! The base rates listed are off season ONLY, higher Memorial Day to Labor Day. Beautiful wooded property and...
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    Location Information
    East Hampton, Hamptons 11937
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Beachy Keen - East Hampton NY1 / 14
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2016
    We stayed for four days. The house is very nice and just as depicted in the photos. Pam was very gracious and very accommodating. She was very flexible with arrival and...
    Reviewed August 4, 2016
    Very cute and homey house, great hosts and a good location in the Hamptons. Close to Sag Harbor and East Hampton and close to the water. The pool is really nice and clean and...
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    About this property
    Spend time relaxing by the heated pool or enjoying the nearby beautiful ocean and bay beaches of the Hamptons. This charming air-conditioned home is sited on a privately landscaped half acre property. An open light filled great room floor plan with double height ceiling. Ample decking for lounging...
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    East Hampton, Hamptons 11937
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    7 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    About this property
    9 unique acres in the number 1 zip code in American, and backed up again 40 acres of Green belt. My home is one of 3 structures on the property, the Main house, Carriage, and the Cottage. The Main house is 6 bedrooms and the Carriage house is a Master suite with 900sq feet boasting a beautiful...
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    Sagaponack, Hamptons 11962
    Rental Home - 7 Bedrooms, 4 Bathrooms, Sleeps 20
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Built in 1828 for a ship’s captain, this historic property remains as one of the oldest structures in the village. Original details abound. Large, bright & airy rooms. Brand new furnishings. Perfect for entertaining or a quiet weekend retreat. The Space Located on a tree lined street this...
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    Greenport, North Fork 11944
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    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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    Hampton Bays, Southampton 11946
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    Waterfront Southampton Gem!  Sailboat On Grounds - Travertine patio and Hot Tub1 / 10
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Modern 3+ Bedrm/2.5 Bathrm with 70' WATERFRONT in luxurious Water Mill. Leave your car home! 2 Minute stroll to Village for bagels in the morning and Suki Zuki sushi (restaurant) in the evening. Bike/Walk to Ocean/Beach (1.5 Mile). 5 minute walk to Luxury Hampton Jitney Bus from Manhattan. New...
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    Water Mill, Hamptons 11976
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    About this property
    BEAUTIFUL BAYFRONT HOUSE AND SEPARATE GUEST COTTAGE !! Near all, restaurants, movie theaters, town, 7/11,Star Bucks, Dunkin Donuts TRAIN, fishing, ocean beaches, swimming and all water activities. BBQ, eat on the deck watch the boats go by. Private fenced in yard. Awesome views of Shinnecock...
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    Hampton Bays, Southampton 11946
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    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
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Westhampton Beach Village  LONG ISLAND New York1 / 15
    (3)Terrible
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    About this property
    Beautiful home secluded area. Just renovated. Near everything ocean and beaches. Big backyard. Sports play. Outdoor kitchen-Pool-outdoor shower-circular driveway-6 cars parking. Huge kitchen island and bar sink. 3 masters suites second floor. 3 others large sizes 1st floor. Finished basement too....
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    Westhampton Beach, Hamptons 11978
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    PRISTINE GETAWAY, WITHIN SHORT WALK OF TWO WHITE, SANDY, SOUND BEACHES1 / 17
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Central Heating
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 3, 2016
    What a lucky find. This home has everything - location, setup and an owner to gives you complete backup for your holiday break.
    Reviewed September 24, 2015
    We had a wonderful time at Hickory House. The location in Southold is perfect for visiting the beach, wineries and farmers markets as well as Greenport and Mattituck. The home...
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    About this property
    3 bedrooms, 2 1/2 baths, sleeps 6 private Pristine, year round, vacation getaway, within 5 minute walk to two white, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, clean, smoke free home....
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    Location Information
    Southold, North Fork 11971
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Summer getaway located in the heart of beach country. 3,100 square foot private & spacious house with 5 bedrooms, 3 1/2 baths, 20x40 pool (w/new heater!), hot tub and tennis court situated on a full acre in the most desirable section of East Quogue. When you walk in the door you will be greeted...
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    Location Information
    East Quogue, Hamptons 11942
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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