We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals with Pools in Long Island, NY

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    €0
    €941 Average
    €1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Long Island are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    Clear All
    1 / 24
    5 of 5 bubbles (13) Excellent
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 14
    5 of 5 bubbles (7) Excellent
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 19
    East Hampton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 22
    5 of 5 bubbles (1) Excellent
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Wi-Fi
    • Balcony
    • Secure Parking
    • Porch
    • Air Conditioning
    • Outdoor Dining Area
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    When we vacation we want spotless remodeled accommodations near everything interesting. How about you? Our home is quiet, relaxing, and close to all. Best yet, you'll have your very own 20'x40' salt water pool to enjoy, and you're a 5 minute walk to a private beach.This is a pristine home with... View all property information
    Location Information
    East Hampton, Hamptons 11937
    5 of 5 bubbles Reviewed 3 September 2016
    A few miles out of East Hampton, a short walk to the beech. Great spot for peace and quiet and our kids just loved the (for a family house) large deep pool for jumping and...
    See all reviews
    1 / 28
    5 of 5 bubbles (4) Excellent
    Sag Harbor
    5 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Patio
    • Private Outdoor...
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    1 / 27
    Hampton Bays
    3 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Hampton Bays, Hamptons 11946
    1 / 16
    5 of 5 bubbles (2) Excellent
    Huntington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Shared Garden
    • Central Heating
    • Parking
    • Washer
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ground floor of hi ranch includes large LR/kitchen combo and separate BR. Fully furnished with brand new queen sized bed with Simmons beauty rest 12" mattress! There is also a pullout couch, new flooring, etc. You will have key to house & separate apt. to come & go as you please. In season there is... View all property information
    Location Information
    Huntington, Long Island 11743
    5 of 5 bubbles Reviewed 7 January 2017
    This was my second year in a row staying here. I never have a problem with anything but if I did, Rob is right upstairs and ready to fix it. I would definietly recommend this...
    5 of 5 bubbles Reviewed 18 January 2016
    My friend and I went up for new years. Rob was very nice to us. He informed us where things were locally and how to get to the train station. He gave us our privacy. No problems...
    See all reviews
    1 / 29
    Shirley
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Private Outdoor...
    • Patio
    • Hot Tub
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Luxury Long Island 4-bed home, in Shirley NY, Located on the corner of a quiet street, close to the beach, parks, shopping, night entertainment and movie theater. Mini-golf course in backyard, I/G pool, fire pit, BBQ, 4 BRs available for rental or entire house. The house is about 2,900 SF, on an... View all property information
    Location Information
    Shirley, Long Island 11967
    1 / 15
    5 of 5 bubbles (4) Excellent
    Long Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Washer
    • DVD Player
    • Private Outdoor...
    • Satellite TV
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Long Beach, Long Island 11561
    5 of 5 bubbles Reviewed 20 August 2015
    As I walked into the house for the weekend that we spent there for my sister's bachelorette party, I was in awe of how gorgeous the property was. The house was absolutely...
    5 of 5 bubbles Reviewed 25 February 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...
    See all reviews
    1 / 71
    5 of 5 bubbles (3) Excellent
    Hampton Bays
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Patio
    • DVD Player
    • Hot Tub
    • Private Outdoor...
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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. Large deck with BBQ. Fully equipped kitchen. Wi-fi internet and premium channels cable tv. Pool table, basketball and children play ground for entertainment. Five min... View all property information
    Location Information
    Hampton Bays, Hamptons 11946
    5 of 5 bubbles Reviewed 3 September 2016
    It is a very big and clean house with a big pool. Our families are so enjoy the time of staying here, and the homeowner is very helpful before and during the stay.
    5 of 5 bubbles Reviewed 31 August 2015
    This is a great vacation spot! Recently went with a group of 10 girls and had a great time! Owners are very accommodating, house is very clean and neat. The house is in great...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 27
    Hampton Bays
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    • Private Outdoor...
    • Wi-Fi
    • Balcony
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Updated recently , professionally painted, this home has a cozy feel,open plan available indoors. First floor has for guests : 2 Queen size bedrooms, 2 full marble bathrooms, formal blue dining room,fully equipped and renovated marble kitchen,(stainless steel appliances, incl. dishwasher), also a... View all property information
    Location Information
    Hampton Bays, Hamptons 11946
    1 / 24
    5 of 5 bubbles (6) Excellent
    Montauk
    6 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Internet Access
    • Satellite TV
    • Private Outdoor...
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    East Hampton Rental Registry #16185 *** Please see Summer 2017 (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... View all property information
    Location Information
    Montauk, Hamptons 11954
    5 of 5 bubbles Reviewed 7 July 2016
    Came with a group of girlfriends to relax and enjoy Montauk at the end of the off-season - it was a great house for a bunch of adults to hang, and was well also well set up for...
    5 of 5 bubbles Reviewed 6 December 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...
    See all reviews
    1 / 17
    5 of 5 bubbles (2) Excellent
    Quogue
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Patio
    • Private Outdoor...
    • Air Conditioning
    • Internet Access
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Will your mom have to sit on the end of your futon with a plate of turkey and stuffing balanced on her knee? Will your mother in-law fill your entire kitchen.... with herself... only to find out the Turkey she bought doesn't fit in your oven? Well it is time to escape to beautiful Quogue and have... View all property information
    Location Information
    Quogue, Hamptons 11959
    5 of 5 bubbles Reviewed 23 May 2016
    This house is really awesome. Everything was exactly as described. Owner respond quick to all your questions.
    See all reviews
    1 / 31
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Private Garden
    • Shared Outdoor Pool...
    • Satellite TV
    • Grill
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Charming, spacious, bright and quiet East Hampton home available year round, with a 2 night minimum stay now thru Memorial Day, and a minimum one week stay in the summer months. Bright & Sunny home has wood floors throughout, Cathedral ceiling in open living area with 3 skylights and 3 sets of... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 50
    Southampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Patio
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    If you're planning ahead for summer 2017, this is the time to ask me for a special deal. This open-plan house with second floor gallery and home theater in the basement brings the outdoors in. Wrap-around windows and skylights (plus an AC system with a stun button) gives you the best of the... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 19
    5 of 5 bubbles (1) Excellent
    East Hampton
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor...
    • Air Conditioning
    • Internet Access
    • Patio
    • Satellite TV
    • Grill
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    located only 5 minutes from shops and eateries and 5 minutes to the beach. With a serene setting surrounded by mature trees, this home is a haven for ultimate relaxation and leisure. Enjoy poolside luxury by 20X40 pool in very private yard. Low Allergen Environmentchildren welcomenon smoking... View all property information
    Location Information
    East Hampton, Hamptons 11937
    5 of 5 bubbles Reviewed 27 August 2016
    The owner was attentive and so lovely pointing out the all important designer shoe sale to my daughter and I (yes we did go and get a pair each haha). The house is larger than it...
    See all reviews
    1 / 7
    5 of 5 bubbles (1) Excellent
    East Hampton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • DVD Player
    • Patio
    • Private Outdoor...
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    East Hampton, Hamptons 11937
    5 of 5 bubbles Reviewed 10 June 2016
    My wife and I stayed in this lovely house in May 2016. A lovely quiet area approx. 1/4 mile off the main road so supremely quiet. It was very well furnished and equipped and...
    See all reviews
    1 / 23
    5 of 5 bubbles (1) Excellent
    Cherry Grove
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Internet Access
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    THE MOST DESIRABLE LOCATION IN CHERRY GROVE. ONLY 1 SUMMER WEEK LEFT! 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... View all property information
    Location Information
    Cherry Grove, Fire Island 11742
    5 of 5 bubbles Reviewed 16 October 2016
    My partner and I stayed at this house in the off-season in October. We had such an awesome stay. The homeowners were super friendly and accommodating. Anything we needed they...
    See all reviews
    1 / 18
    5 of 5 bubbles (2) Excellent
    East Hampton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Shared Outdoor Pool...
    • Wi-Fi
    • Satellite TV
    • Hot Tub
    • Patio
    • Housekeeping...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Desirable Northwest Woods home close to East Hampton Village, ocean and bay beaches and Sag Harbor. Access to community association park on Hands Creek - lovely private view with Adirondack chairs. Walk to Hands Creek and Settlers Landing. Short drive to Cedar Point Park with picnic grounds,... View all property information
    Location Information
    East Hampton, Hamptons 11937
    5 of 5 bubbles Reviewed 10 August 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...
    5 of 5 bubbles Reviewed 4 August 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 the...
    See all reviews
    1 / 17
    East Hampton
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    • Grill
    • Secure Parking
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our beautiful four bedroom, two bathroom beach house is newly renovated and available for rent! Located on .7 acres, this property is a dream come true for all those looking for a peaceful escape into one of the most beautiful parts of the country. Our lovely home is located only 7 minutes away... View all property information
    Location Information
    East Hampton, Hamptons 11937
    Get the List
    1 / 16
    East Hampton
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Private Outdoor...
    • Air Conditioning
    • Secure Parking
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Deliciously close to the shimmering bay, is this very special 5 bedroom, 4 bath shingled traditional beautifully sited on a serene 1.8 acre well-landscaped parcel in the desirable Grace Estate area between East Hampton and Sag Harbor. A distinctive coffered ceiling foyer leads to the vaulted living... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 23
    5 of 5 bubbles (3) Excellent
    Hampton Bays
    7 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Washer
    • Private Outdoor...
    • Satellite TV
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Only 600 feet from one of the most beautiful (private) Hampton's beach. Enjoy poolside living in this stunning contemporary home complete with lots of skylights and cathedral ceiling. Bike along the Peconic Bay or enjoy miles of sandy beach just steps away. This spacious home has a large heated... View all property information
    Location Information
    Hampton Bays, Hamptons 11946
    5 of 5 bubbles Reviewed 4 January 2016
    Our family had a lovely time during our stay at this house, the amenities were great and we had a warm welcome when we got there. the pool, hot tub, and game room were all above...
    See all reviews
    1 / 6
    Kings Point
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Parking
    • Private Garden
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful house with an independent studio close to railroad station Beautiful water view. Fishing and paddle boat. Kitchen facilities neat people only We can offer extra bedroom. Shower and pool spa also. Near shopping and restaurants. Internet Wifi and TV room. Deck and Barbeque. You have to see... View all property information
    Location Information
    Kings Point, Long Island 11023
    1 / 20
    4.5 of 5 bubbles (2) Very good
    Remsenburg
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Outdoor...
    • Internet Access
    • Grill
    • Patio
    • Washer
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Easy summer living at this bright contemporary ranch located steps from Moriches bay in Westhampton/Remsenburg. Open kitchen- dining area, living room with fireplace, 3 bedrooms, 2 baths, central air conditioning, and a private yard with a heated swimming pool. <BR><BR>Located on a small quiet... View all property information
    Location Information
    Remsenburg, Long Island 11960
    5 of 5 bubbles Reviewed 16 June 2015
    I welcomed my friends from Germany to the U.S. What made the stay super sweet for them and for myself was this rental. It had everything we needed. I'm a local in Westhampton, so...
    4 of 5 bubbles Reviewed 14 June 2014
    We have rented the house for a long week. The contact with Christine was excellent. The info and the keys were all where they should be. The house is clean even for German...
    See all reviews
    1 / 19
    Wainscott
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • DVD Player
    • Washer
    • Patio
    • Porch
    • Private Outdoor...
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wainscott, Hamptons 11975
    1 / 6
    Fire Island Pines
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool...
    • Hot Tub
    • Ocean Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Fire Island Pines, Fire Island 11782
    1 / 20
    4.5 of 5 bubbles (7) Very good
    Shelter Island Heights
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Grill
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Internet Access
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    With it's Caribbean flair, 3 waterfalls, 2 pools and 75' Koi pond, our Vacation home is possibly the most Romantic Hamptons Hideaway Vacation Cottage Home Rental ever. Located in the Estate Section of Shelter Island. Available weekly, monthly or for the entire season contact us early for your... View all property information
    Location Information
    Shelter Island Heights, Shelter Island 11965
    1 / 15
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Hot Tub
    • Grill
    • Private Outdoor...
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This stunning contemporary house is set on two private acres in the near Northwest Woods. Bright, white filled with sunlight, this four bedroom, two and a half bath multi-level home has soaring cathedral ceilings on the main level, large king master bedroom suite with private deck, TV, new bath... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 16
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Private Outdoor...
    • Grill
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Brand New Chic Saltwater Dark Bottom Pool with Tanning Ledge! Whisper quiet retreat for all seasons in updated contemporary saltbox in East Hampton's NW Woods. Close to beach and charming EH and Sag Harbor! Rental contract required. RR # 161918 Also has wood burning fireplace and firewood... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 5
    3 of 5 bubbles (1) Average
    Montauk
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Royal Atlantic Beach Front Resort , Montauk 1 Bedroom Suite For Rent Minimum of 2 Night Stay Sleeps 4 126 S Emerson Ave, Montauk, NY 11954 ONE BEDROOM VIP SUITE: Located directly across the street from the beach. It has a private balcony facing the pool courtyard. This suite features an open... View all property information
    Location Information
    Montauk, Hamptons 11954
    3 of 5 bubbles Reviewed 26 November 2016
    We have been going to the Royal Atlantic every year except for one year. It has gone downhill for a few years now. We keep going back because of the location. We have a...
    See all reviews
    1 / 23
    Southampton
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Satellite TV
    • Private Outdoor...
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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” House, 5 bedrooms, 5 baths , CAC, hardwood floors, in-ground heated pool, Outdoor... View all property information
    Location Information
    Southampton, Hamptons 11946
    1 / 24
    Water Mill
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • Private Outdoor...
    • Balcony
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Water Mill, Hamptons 11976
    1 / 31
    Southampton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    Amenities & Details
    • Grill
    • Satellite TV
    • Air Conditioning
    • Private Outdoor...
    • DVD Player
    • Parking
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Every season is beautiful here, so relax and get away from it all. Situated at the gateway to the Hamptons, the Easterner Motel is located in charming, bucolic Shinnecock Hills, just five miles from Southampton Village and the famous, stunning beaches of Southampton, and beyond, all the way to the... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 15
    1 of 5 bubbles (3) Terrible
    Westhampton Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 13 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Porch
    • Patio
    • Shared Garden
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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.... View all property information
    Location Information
    Westhampton Beach, Long Island 11978
    1 / 18
    5 of 5 bubbles (3) Excellent
    Orient
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    • DVD Player
    • Patio
    • Private Outdoor...
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy gorgeous water views of Gardiner's Bay from this immaculate Victorian home situated on 1 acre. This spacious and beautifully decorated home comfortably accommodates 8 adults. Beds: 1 King Bed, 2 Queen Beds, 1 Double Bed View all property information
    Location Information
    Orient, North Fork 11957
    1 / 14
    5 of 5 bubbles (3) Excellent
    Montauk
    2 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Indoor Pool
    • Internet Access
    • Patio
    • Washer
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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. This cottage has been in our family for... View all property information
    Location Information
    Montauk, Hamptons 11954
    5 of 5 bubbles Reviewed 24 September 2016
    My husband and I come to Montauk every September - the light is beautiful, beaches less crowded, and we love the combination of warm days and slightly chilly nights. This is a...
    See all reviews
    1 / 13
    Bridgehampton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Private Outdoor...
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    Location Information
    Bridgehampton, Hamptons 11932
    1 / 28
    Southampton
    4 Bedrooms, 5 Bathrooms, Sleeps 7 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • DVD Player
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to your private Hamptons escape! This immaculate Southampton vacation rental house is sure to provide the perfect vacation spot for your next family getaway. Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this gorgeous home is a terrific size and... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 9
    East Quogue
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Secure Parking
    • Satellite TV
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    East Quogue, Hamptons 11942
    1 / 21
    Sagaponack
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Hot Tub
    • DVD Player
    • Washer
    • Air Conditioning
    • Private Outdoor...
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Welcome to the beautiful and immaculate five bedroom, four bathroom house in Sagaponack, New York.  Centrally located...five minute drive from Sag Harbor, five minute drive from the ocean and our amazing beaches.  Pine hardwood floors, contemporary furnishings with all the latest amenities.  Full... View all property information
    Location Information
    Sagaponack, Hamptons 11962
    1 / 55
    5 of 5 bubbles (7) Excellent
    Southampton
    7 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Private Outdoor...
    • Satellite TV
    • Hot Tub
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This is extravagant living at its best. Picture yourself enjoying expansive water views and majestic sunsets. The park like setting lends itself to an idyllic outdoor paradise. This home has 7 huge bedrooms and 5 palatial bathrooms. The house boasts a wide-open floor plan with soaring cathedral... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 36
    Sag Harbor
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Private Outdoor...
    • DVD Player
    • Wi-Fi
    • Grill
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    5 bedrooms, 4.5 full baths. New construction, steps to private beach. Bathrooms of Carrara marble and polished chrome finishes. Open living/dinning and family room with 2 fireplaces. Mahogany deck and beautiful 20x40 Gunite heated pool with Danish brick patio. Gourmet country kitchen with... View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    1 / 22
    East Hampton
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Grill
    • Air Conditioning
    • Washer
    • Wi-Fi
    • DVD Player
    • Housekeeping...
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This Contemporary home (Arch-Robert Barns Design) is situated atop a 4.25 acre flag lot and abuts a 17.5 acre nature preserve for complete privacy. This contemporary home has been recently renovated with no expense speared featuring all new top of the line finishes. The home features large windows... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 27
    Southampton
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Hot Tub
    • Private Outdoor...
    • Patio
    • Air Conditioning
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Newly build home, no expense spared. Beautiful pool and outdoor dining and cooking/BBQ area. The prefect home for entertaining and relaxing. Fully equipped kitchen for cooking and dining, plenty of space for entertaining. Master bedroom is fit for royalty, 4 more beautiful bedrooms in main house.... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 18
    5 of 5 bubbles (1) Excellent
    Glen Cove
    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Sauna
    • Hot Tub
    • Private Outdoor...
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful home close to beaches, parks and less than 1 hour via nearby train to NYC. The original "Gold Coast" Glen Cove and the surrounding areas of Locust Valley, Sea Cliff, Oyster Bay, Lattingtown, Bayville and the Brookvilles. Playground for the rich and famous, who prefer to keep a low... View all property information
    Location Information
    Glen Cove, Long Island 11542
    1 / 31
    5 of 5 bubbles (1) Excellent
    Hampton Bays
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor...
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    For families w or w/o kids or group adults over 30 years old up to max.8 guests inquire with your specific details for availability. Min.2 nights JUN or SEP, 3 nights for Memorial Day or Labor Day, 4 nights for JUL-AUG. EXTRA at check-in: 180$ cleaning fee + refundable sec.deposit up to 48h... View all property information
    Location Information
    Hampton Bays, Hamptons 11946
    1 / 24
    Amagansett
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Balcony
    • Hot Tub
    • Private Outdoor...
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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, this classic five bedroom, four and one-half bath traditional has every amenity and plenty of style. There's lots of open space for living including a lovely great room... View all property information
    Location Information
    Amagansett, Hamptons 11930
    1 / 19
    5 of 5 bubbles (2) Excellent
    Bridgehampton
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Parking
    • Washer
    • Private Outdoor...
    • Air Conditioning
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Bridgehampton, Hamptons 11932
    5 of 5 bubbles Reviewed 2 weeks ago
    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 located...
    See all reviews
    1 / 12
    Water Mill
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Grill
    • Air Conditioning
    • DVD Player
    • Patio
    • Washer
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    5 bed 4 bath, heated pool, kid and pet friendly 5 bedroom, 4 bath, newly renovated home in Water Mill section of Southampton. Close to town and beaches, heated pool, kids play set, sand box and basketball hoop on close to an acre. Wood burning fireplace, new floors and modern kitchen with... View all property information
    Location Information
    Water Mill, Hamptons 11976
    1 / 25
    4.5 of 5 bubbles (6) Very good
    Hampton Bays
    9 Bedrooms, 4 Bathrooms, Sleeps 18 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Hot Tub
    • Washer
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Walk to beach. Enjoy sunsets over the bay in this beautifully designed contemporary central hall Colonial on 1.6 acres. Extremely large 9 bedrooms, 3.5 baths with state-of-the-art kitchen, formal dining room, large living room with fireplace and billiard room , ping pong room and full exercise gym.... View all property information
    Location Information
    Hampton Bays, Hamptons 11946
    5 of 5 bubbles Reviewed 4 January 2016
    My family and I stayed here for our annual family reunion. We had the best time of our lives. The pool was clean and heated and the hot tub was perfect for those cool nights. My...
    5 of 5 bubbles Reviewed 15 July 2015
    This was truly a beautiful home with all the amenities we needed. The pool was sparkling clean and the hot tub super warm. We were amazed at how large all the bedrooms were. The...
    See all reviews