Top 10 Vacation Rentals With Private Pool In Long Island, New York

vacation rentals with private pool long island

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.

1. Elegant rental with panoramic views of the ocean (from USD 2736)

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.

Luxury Oceanfront House! pool+Jacuzzi facing the ocean Call for Spring Getaway!
Westhampton Beach, NY, US
6 Bedrooms 5 Bathrooms

2. Beautiful abode for 14 guests (from USD 975)

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.

Luxury Hamptons Vacation Home With Heated Pool, Hot Tub & Brand New Tennis Court
43 reviews
House 6 Bedrooms 6 Bathrooms
Top guest reviews
Amenities & Room:
the pool deck and tennis courts were in great shape and seemed brand new
and the amenities including a large pool basketball court and tennis court were a huge hit with all
and it was clean
the property itself is super spacious clean and well taken care of
dustin was a great host
the owner was quickly responsive for any questions that came up during our stay
the owner was super responsive to all of our needs and all of the information provided was clear
everything we needed was there and the owner was super responsive to questions
dustin the host was so great to work with
the location is also great close to town and the beaches
the house is in an excellent location close to a lot of the best wineries on long island
the location is great visited the quogue wildlife refuge and lots of shopping at tangier
this 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 sunblock
Read more reviews

3. Homey rental located within a garden (from USD 1500)

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.

Mint 5-BR Gem in Southampton Village, Heated Gunite Pool, walk to beach and town
Southampton, NY, US
5 Bedrooms 5 Bathrooms

4. Stylish house with bay views (from USD 846)

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.

4 BR/3 Bath with beautiful bay views and private heated pool (seasonal)
40 reviews
House 4 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
both living rooms are equipped with comfortable furniture
the view from the balcony every morning was just perfect the house was super clean & cozy
the saltwater pool is stunning we spent most of our days in it
the pool is great and it’s a relaxed place to let the world go by
our group loved the house we loved the indoor-outdoor living by the pool and enjoyed meals on the porch
everything was super clean upon arrival and we were very comfortable the whole time
the beds and pillows were comfy with clean white sheets
house is clean and actually nicer in person than the photos
this home was perfect owners were extraordinarily accommodating
owners were awesome provided us a very detailed welcome packet with recommendations to their favorite places
the owner were super responsive and everything was easy
she was incredibly responsive throughout and also very flexible
tara was super helpful and quick to respond to all my questions
awesome water views quiet neighborhood in easy driving distance to some great restaurants vineyards and beaches
easy to get to from nyc and plenty of places to eat and shop nearby
Read more reviews

5. Lovely rental with outdoor entertainment (from USD 1492)

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.

Pure Luxury living In This 12,000 SF Estate
33 reviews
House 6 Bedrooms 9 Bathrooms
Top guest reviews
Amenities & Room:
almost all of the many rooms come with tv and the wifi is very good
the heated pool was perfect for the weather
huge kitchen with all the essentials and lots of seating
however the place itself is stunning clean and gorgeous
beautiful spacious and clean home with a great game room huge pool and lovely outdoor space
we had a great time staying here everything was thoroughly cleaned and the property was beautiful
beautiful house and amenities very clean easy communication convenient location from the city
heidi was a fantastic host and i would highly recommend anyone to stay at this beautiful home
heidi was a fantastic host and i would highly recommend anyone to stay at this beautiful home
during the booking and check-in process she was incredibly responsive and helpful
during the booking and check-in process she was incredibly responsive and helpful
heidi was very helpful and easy to communicate with throughout our stay
just an hour away from nyc is this gorgeous mansion that is a perfect place for families and friends
Read more reviews

6. Waterfront haven near a dock (from USD 775)

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.

Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub
Westhampton, NY, US
35 reviews
House 6 Bedrooms 4 Bathrooms
Top guest reviews
Amenities & Room:
the back patio and grill were great but the star of the show was the pool
large rooms and comfortable for our group of ten adults and five small children
the outdoor yard and pool and hot tub were perfect for our needs
the eclectic decor kept us entertained for hours and the hot tub and pool were beyond expectation
the house was clean very comfortable and spacious
beautiful property spacious clean close to town
the owner brian was very kind and let us both check in early and check out late
the owner was very helpful & accurate with the description of the entire process
Read more reviews

7. Secluded estate for 12 guests (from USD 899)

This Victorian-style estate guarantees guests a quiet stay as it is in a tranquil area. North Fork is just 20 minutes away, so venturing out is easy. A 20x40 inground private pool charms you with its gorgeous waterfall and lush greenery surroundings. The loungers in the pool area let you relax and enjoy the sun. There is a basketball court, pool table, ping pong table, and video games for amusement. The kitchen is fully functional and comes with a stove, oven, microwave, coffee maker, toaster, grill, fridge, and dishwasher.

Estate setting at the gateway to the Hamptons.
59 reviews
House 5 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
the backyard is exceptional with bbq fire pit playground for young kids and a beautiful heated pool
the back yard and pool are amazing and will make you never want to leave there
the house is gorgeous spacious clean and fully stocked
my friends and i were amazed at how beautiful clean and comfortable is property was
sebastian was an amazing host and the house was beautiful super clean and comfortable
seb was very helpful and very lenient
thank you for allowing us the opportunity to enjoy your home and being such a gracious host
the host was incredibly welcoming and was available for any questions we had
the owner was very responsive and very helpful
sebastian was a wonderful host for our family vacation
the house is in a great quiet location
Read more reviews

8. Cozy hideaway with private beach access (from USD 625)

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.

Beach, Pool, Wine, Shopping!
36 reviews
House 2 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
we all enjoyed the gorgeous outdoor area with pool and grill enjoying the fresh air
the pool and patio turned out to be our favorite place to relax together as a family
the house was equipped with everything we needed for cooking and relaxing by the pool
we played ping-pong in the (giant) pool house and ate a grilled dinner every night on the deck
the house is beautiful perfect for a comfortable and relaxing stay with the whole family
it's clean spacious and beautifully decorated
the house was very clean and the master bed was extra large and so comfortable
property was clean and very cute and the pictures online were exactly what we got
the owners are very responsive to questions
shawn was especially helpful with any questions we had
shawn was very helpful and accessible and a most gracious host
the owner was very responsive informative and accommodating
the owner shawn was very nice and responsive when he needed to speak with him
the location is great
excellent location close to groceries/supermarket
the house is close to town and in a very cute neighborhood
the grounds are spacious and beautiful and love lane is just a short walk away
my friends and i enjoyed the location of this property
Read more reviews

9. Pleasant cottage for a small family (from USD 479)

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.

82 reviews
cottage 2 Bedrooms 2 Bathrooms
Top guest reviews
everything was very clean and andrew was a great host
the home was clean and comfortable
the property manager was super nice and helpful
the host was a fantastic communicator
lovely area and property wonderful host
very friendly and helpful host who has everything laid out ready for guests
great house host was super sweet and accommodating
it was the perfection location for wineries exploring north fork fun
Read more reviews

10. Quaint farmhouse near a beach (from USD 1000)

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.

Cozy Farm House Retreat in The Quaint Hamlet of Remsenburg With Heated Pool
Remsenburg-Speonk, NY, US
3 Bedrooms 2 Bathrooms

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.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

Get Trip101 in your inbox

Unsubscribe in one click. See our privacy policy for more information on how we use your data

I am a travel writer and obviously love to travel. Traveling is a spiritual experience and I am crazy about it. I explore the wonders of the world through my writing.

 Want to contribute as a Local Expert?
Explore Long Island
Good things are meant to be shared!