Blessed with coastal charm, Long Island in New York is the ideal vacation spot for those who love to escape the routine. Treat your kids to endless fun at Long Island Aquarium; enjoy the stupendous views of the Atlantic Ocean from Montauk Point Lighthouse; stroll through the Jones Beach State Park; tour the picture-perfect Brooklyn Botanic Garden; and admire the stunning facade of Oheka Castle. Gorgeous beaches, exquisite dining options, and brilliant wineries also await you in North Fork town. With an abundance of historical and natural attractions, this destination attracts all types of tourists. Before booking your accommodation, check out our list of the top vacation rentals with private pool in Long Island, New York.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on October 23, 2024.
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1. Elegant rental with panoramic views of the ocean (from USD 2298)
This stunning property stands out with its beachfront location and a wide array of updated amenities. The attractive mahogany deck features a gunite pool, plunge pool, and a hot tub overlooking the beach. There are balconies to admire the dazzling sunset or enjoy the cool breeze. If you are planning to cook, there is a well-appointed kitchen with two dishwashers and a refrigerator. You can either dine inside or outside, as there is a nice dining set in the kitchen area and on the patio.
2. Beautiful abode for 14 guests (from USD 900)
This beautiful home is designed with a contemporary look to offer a warm holiday experience. A private pool, a hot tub for six guests, and an outdoor shower are enough to keep you refreshed throughout your stay. For some entertainment, you have a tennis court, foosball table, and pool table at your disposal. Alternatively, you can also grill some meat or just stroll through the nearby beaches. This rental has free Wi-Fi, so you never have to worry about staying connected with people back home.
Top guest reviews
Host:
dustin was a great hostthe owner was quickly responsive for any questions that came up during our staythe owner was super responsive to all of our needs and all of the information provided was cleareverything we needed was there and the owner was super responsive to questionsdustin the host was so great to work withLocation:
the location is also great close to town and the beachesthe house is in an excellent location close to a lot of the best wineries on long islandthe location is great visited the quogue wildlife refuge and lots of shopping at tangierthis house is in a great location in quogue just minutes from the beach wineries and great restaurants- to make it an easy place to visit without much more than your swimsuit and sunblockRead more reviewsAmenities & Room:
the pool deck and tennis courts were in great shape and seemed brand newand the amenities including a large pool basketball court and tennis court were a huge hit with all
3. Homey rental located within a garden (from USD 1425)
The fun never ends at this inviting abode with an attractive exterior. Located within a tropical garden, its outdoor area is beautifully designed with a durable private pool bordered by a bluestone patio. Here, you can relax on the lounge chairs or simply grill food and relish it outdoors under the portico. You can also make use of the picnic table that is surrounded by rose garden which has been here for 50 years now. This rental has five bedrooms and five bathrooms, making it the ideal hideaway for ten guests.
4. Lovely rental with outdoor entertainment (from USD 1300)
If you are planning a vacation with a large family and friends, book this outstanding six-bedroom rental. A heated private pool with a pool house surrounded by loungers enables you to take a dip anytime or simply destress. Inside, you will find a kitchen with two granite islands as well as a library with built-in cabinetry and hidden doors. Additionally, you will also have access to a tennis court and golf course for outdoor fun. Other notable amenities include a movie room, gym, and play area.
Top guest reviews
Host:
heidi was a fantastic host and i would highly recommend anyone to stay at this beautiful homeheidi was a fantastic host and i would highly recommend anyone to stay at this beautiful homeduring the booking and check-in process she was incredibly responsive and helpfulduring the booking and check-in process she was incredibly responsive and helpfulheidi was very helpful and easy to communicate with throughout our stayLocation:
just an hour away from nyc is this gorgeous mansion that is a perfect place for families and friendsCleanliness:
however the place itself is stunning clean and gorgeousbeautiful spacious and clean home with a great game room huge pool and lovely outdoor spacewe had a great time staying here everything was thoroughly cleaned and the property was beautifulbeautiful house and amenities very clean easy communication convenient location from the cityRead more reviewsAmenities & Room:
almost all of the many rooms come with tv and the wifi is very goodthe heated pool was perfect for the weatherhuge kitchen with all the essentials and lots of seating
5. Waterfront haven near a dock (from USD 760)
Get ready to experience the Hampton lifestyle at this immaculate waterfront home. The outdoor area comes complete with a heated private pool and a hot tub for eight people to enjoy some rejuvenating moments. Planning to explore the waters? Well, you can then walk down to the dock where any size of boat can be moored. If you need to catch up on some work, you may do so with the dedicated workspace, computer, printer, fax, and internet connection provided.
Top guest reviews
Host:
the owner brian was very kind and let us both check in early and check out latethe owner was very helpful & accurate with the description of the entire processCleanliness:
the house was clean very comfortable and spaciousbeautiful property spacious clean close to townRead more reviewsAmenities & Room:
the back patio and grill were great but the star of the show was the poollarge rooms and comfortable for our group of ten adults and five small childrenthe outdoor yard and pool and hot tub were perfect for our needsthe eclectic decor kept us entertained for hours and the hot tub and pool were beyond expectation
6. Cozy hideaway with private beach access (from USD 350)
This charming house is located three minutes away from the private beach. The wineries in North Fork can be accessed within a short drive, while Manhattan is a 90-minute drive away. A king bed, a queen bed, and a queen-sized sofa bed are available to offer restful nights for six guests. When you are not visiting the beach, you can take a cool dip in the private pool nestled within the garden. If you wish to spend your day indoors, there is ping pong, board games, and books.
Top guest reviews
Host:
the owners are very responsive to questionsshawn was especially helpful with any questions we hadshawn was very helpful and accessible and a most gracious hostthe owner was very responsive informative and accommodatingthe owner shawn was very nice and responsive when he needed to speak with himLocation:
the location is greatexcellent location close to groceries/supermarketthe house is close to town and in a very cute neighborhoodthe grounds are spacious and beautiful and love lane is just a short walk awaymy friends and i enjoyed the location of this propertyCleanliness:
it's clean spacious and beautifully decoratedthe house was very clean and the master bed was extra large and so comfortableproperty was clean and very cute and the pictures online were exactly what we gotRead more reviewsAmenities & Room:
we all enjoyed the gorgeous outdoor area with pool and grill enjoying the fresh airthe pool and patio turned out to be our favorite place to relax together as a familythe house was equipped with everything we needed for cooking and relaxing by the poolwe played ping-pong in the (giant) pool house and ate a grilled dinner every night on the deckthe house is beautiful perfect for a comfortable and relaxing stay with the whole family
7. Pleasant cottage for a small family (from USD 760)
This 100-year-old barn-turned cottage guarantees guests a quiet and fun holiday. For relaxation, you can swim in the gunite private pool with mineral saltwater or soak in the hot tub to soothe the stressed body. If you are lucky, you can catch the sunset view from the pool. The yard is neatly manicured and includes a seating area with a wood-burning fire pit. A king bed, two queen-sized sofa beds, and two sleeper sofas can sleep up to six people.
Top guest reviews
Host:
we had the greatest time amazing host and amazing propertythe owner was easy to communicate with and very responsive with any of our needsandrew was friendly and accommodatingandrew was very pleasant and informativeLocation:
the location was perfect for what we wanted to dothe hot tub was a great bonus and the location is close to everything on the north forkit was a great location to easily get around and loved the amenities offeredCleanliness:
everything was very clean and organizedthe pool and hottub were clean and beautifuleverything was clean and ready for our stayRead more reviewsAmenities & Room:
spent a lovely weekend with a few friends and thoroughly enjoyed the pool and other amenitiesthe pool hot tub and fire place were great
8. Quaint farmhouse near a beach (from USD 860)
Set in Remsenburg, this impeccable property allows you to have a blissful vacation with your family and friends. It is located 5 minutes from Westhampton Village, 10 minutes from the white sandy beach, and 15 minutes from North Fork wineries. The gazebo with a dining table is the center of attraction in this house. You will be amazed to dive into the heated private pool in which the shallow side is suitable even for kids. There is a fire pit with sofas for your chilly nights.
9. Stylish house with bay views (from USD 850)
This enchanting house has a lot of space to accommodate 10 guests with its 4 bedrooms and 3 bathrooms. There is a private beach with fishing, paddle boarding, and boating options nearby. Since it is located near the sea, you get to wake up to unparalleled water views. You can also enjoy a game of foosball and air hockey within the property. During your leisure time, you can go for a swim in the heated pool overlooking the hedges or simply relax on the deck.
Top guest reviews
Host:
this home was perfect owners were extraordinarily accommodatingowners were awesome provided us a very detailed welcome packet with recommendations to their favorite placesthe owner were super responsive and everything was easyshe was incredibly responsive throughout and also very flexibletara was super helpful and quick to respond to all my questionsLocation:
awesome water views quiet neighborhood in easy driving distance to some great restaurants vineyards and beacheseasy to get to from nyc and plenty of places to eat and shop nearbyCleanliness:
everything was super clean upon arrival and we were very comfortable the whole timethe beds and pillows were comfy with clean white sheetshouse is clean and actually nicer in person than the photosRead more reviewsAmenities & Room:
both living rooms are equipped with comfortable furniturethe view from the balcony every morning was just perfect the house was super clean & cozythe saltwater pool is stunning we spent most of our days in itthe pool is great and it’s a relaxed place to let the world go byour group loved the house we loved the indoor-outdoor living by the pool and enjoyed meals on the porch
Have a fun-filled holiday in Long Island
With a combination of nature and history, Long Island is truly a tourist paradise. Every part of the island is replete with unrivaled attractions or an amazing array of activities. Book from one of our top vacation rentals in this area and enjoy your holiday like never before.
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