Montauk is known for its laidback vibe. It may be a small portion of Long Island, but it offers plenty of attractions worth seeing. At Montauk Point State Park, you will find the state’s oldest lighthouse. If you want to do more than admire the scenic lighthouse views, you can hit the hiking and skiing trails, or have fun at one of the local surf fishing sites. Another famous attraction for fishing enthusiasts is Lake Montauk. Currently, it serves as a tiny port for fishing boats. You can spend a fine day on a chartered fishing boat. If the purpose of your trip is to recharge, you should stay at one of the best vacation rentals with private pool in Montauk, New York. Check them out below.
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 27, 2025.
1. Luxury home with easy lake access (from USD 2294)
This luxury house is your ideal base camp for a leisurely holiday in Montauk. It has a spacious backyard where the kids can have fun in the sun. While the young ones play, you can grill meat and prepare home-cooked meals. After eating, you can head to the nearby lake. The host provides kayaks and paddleboards for guests’ use.
If you do not feel like going out, you can admire the stunning views from the infinity pool. This pool is open between Memorial Day weekend and October 1.
Montauk, New York, United States
Top guest reviews
Host:
property manager was very responsivehome owner was immediately responsive when we had a questiontabitha and erin were both so kind and helpfulLocation:
location is perfect on the lake close to town and lots of hiking all aroundclose enough to yummy food coffee and the beach without being anywhere near traffic and crowdsnice and quiet in the off seasonCleanliness:
clean rooms amazing views infinity pool and ample parking for my party of 12Read more reviewsAmenities & Room:
beautiful property fantastic views super comfortable beds well-equipped kitchenthe house fit 15 of us comfortable and exceeded expectationsliving space/kitchen is large and has an amazing viewthe rooms were large and neatly keptit's spotless comfortable and the view is superb
2. Charming sanctuary with a covered front porch (from USD 694)
Set at the heart of a 0.2-hectare (0.5-acre) property on the end of a private road in Montauk, this charming house ensures a quiet holiday. It features a rear cedar deck tailored for outdoor lounging. When you get up in the morning, you can enjoy the fresh air on the covered front porch while having your tea or coffee.
This rental also offers a private swimming pool so that you can have a refreshing soak. Lounge chairs surround the pool area, so feel free to sunbathe and get that tan.
Montauk, New York, United States
Top guest reviews
Host:
property management company very responsiveall appliances in the kitchen worked and both owner and property manager were very responsivethe caretaker chris was friendly and helpfulRead more reviewsLocation:
great location for all that montauk has to offerperfect location to ride a bicycle to the beach
3. House with a private outdoor shower
This house provides 222.97 sq m (2,400 sq ft) of living space suitable for huge families. It guarantees you a leisurely stay, giving you many options for entertainment.
On the spacious deck, you can have a fun family barbecue. After eating, you can enjoy a decent nap in the climate-controlled pool house. You can take a dip in the heated swimming pool when you get up. This swimming pool is accessible between May and October. Before entering the property from the beach, ensure that you rinse off using the private outdoor shower.
Montauk, New York, United States
Top guest reviews
Host:
carter is the best host you can ask forcarter was a great host attentive to what we neededvery nice and helpful ownerthank you so much carter and kate for hosting usthe home was toddler friendly and our family was quite comfortable during our stayLocation:
great location to town and beachabsolutely beautiful house with perfect location for montauk’s beach and townloved this property perfect location and setting for a girls getawaythe beach is a quick walk away easy for multiple visits every dayRead more reviewsAmenities & Room:
great property with a private fenced backyard and a beautiful pool and hot tub
4. Delightful retreat with water views
Are you seeking a rejuvenating retreat in Montauk? This house surrounded by scenic views is perfect for you. It features a large deck, an ideal spot for watching the sunrise while having your coffee. At night, you can hang out on the second-level wraparound deck and enjoy the calming ocean breeze. This rental also offers a swimming pool that’s open seasonally between Memorial Day and Labor Day.
Montauk, New York, United States
Top guest reviews
Host:
she was attentive and kindshe was available helpful and accommodatingshe was extremely responsive to any questions i had from pre-booking right through the end of our stayCleanliness:
her house was so clean and comfortable as well as spaciouscomfortable and clean and so close to everything montauk loved our stayRead more reviewsAmenities & Room:
the house was well laid out and the backyard allowed for relaxing afternoons by the poolbeautiful home w great yard and pool areaand the yard was great we used the pool every day
5. Contemporary home with a fire pit (from USD 18332)
An ideal holiday destination for families, this contemporary home offers many recreational facilities. It has an outdoor fire pit that’s accessible every summer. If you wish to go out, you can use the kayaks and standup paddleboards that are provided and hit the waters. A secluded beach is only a five-minute walk away. Alternatively, you can splash around the heated swimming pool. It even comes with a slide that your kids will enjoy.
Montauk, New York, United StatesSuperhost
Accommodates: 10
Top guest reviews
Host:
the home was very clean and the hosts were responsive to questions during our stayLocation:
great house in a great locationbeautiful location and inside is all modern updatedkitchen is gorgeous so close to beautiful beach and quiet neighborhood we truly enjoyed the staythe house was beautiful sunsets were magnificent perfect location close enough to town and beautiful viewsCleanliness:
home very clean and cozythe house itself is well laid out tastefully decorated and cleanRead more reviewsAmenities & Room:
the pool was awesome and the view was unbelievablethe pool was beautiful and the kitchen modern
6. Multi-level beach retreat (from USD 5777)
Catering to families visiting Montauk for vacation, this vibrant home offers three main living areas. It has a gourmet kitchen with many high-end appliances, making it easy for you to prepare meals for the whole family. Meanwhile, the outdoor space features a deck, patio, and lounge with a TV.
If you want to relax further, you can dip in the swimming pool. Note that this swimming pool is open between mid-May and mid-October. After swimming, you can wash your wet clothes immediately because two laundry rooms are at your disposal.
Montauk, New York, United StatesAccommodates: 10
Top guest reviews
Host:
tabitha was a wonderful and attentive hostLocation:
beautiful new home with amazing location close to easy beach accessgreat location quick drive from town on a quiet streetamenities and location were outstandingthe house is beautiful very close to the beach and everything you could want for a beach vacationRead more reviewsCleanliness:
the house was clean and well maintainedhouse itself has all the bells and whistles relaxing pool area and is very cleanthis home is magnificent it was sparkling clean spacious and nicely decorated
7. Unique property with private beach access (from USD 2051)
This beach-inspired home boasts an inviting indoor living space, allowing you to laze around and relax all day. You can spend quality time in the family room and enjoy meals in the huge dining room. Nonetheless, this property is only a three-minute walk from Culloden Point. You’ll have private beach access, so you can easily head out to get sun-kissed.
On the other hand, you may also spend worry-free hours in the heated swimming pool. It is accessible seasonally between Memorial Day and September 30.
Montauk, New York, United StatesAccommodates: 6
Top guest reviews
Host:
lilliana is a great hostlilliana was very quick and responsive to any questions we hadthe host is extremely responsive and helpfultabitha was extremely professional and most importantly she was super attentiveLocation:
best parts: locationcharming house great location attentive hostesslocation was great a 2 minute walk to a private beach and just a short drive into townthis is house is such a great find in a great locationlilliana’s house was beautiful and in a great location—just a quick walk to the beachCleanliness:
the house itself was really great and was very clean lovely and comfortablea great home lovely decor clean open layout great lightthe montauk home was clean and beautiful and the photos depicted it very accuratelyRead more reviewsAmenities & Room:
backyard pool which was terrific for an afternoon swim after the beach
8. Serene four-bedroom home (from USD 1350)
Are you planning a much-needed family vacation in Montauk? This home in a friendly neighborhood is worth considering, especially if you have the budget. It has a well-equipped kitchen that you may use to cook food for your loved ones at any time. After sharing a meal, you can head out to the pool area and enjoy a refreshing swim. Thanks to the washer and dryer provided, you can easily wash and dry your swimwear.
Montauk, New York, United StatesAccommodates: 8
Top guest reviews
Host:
super responsive and communicative hostLocation:
beautiful property and great locationgreat location and sushil was highly responsivealso great location and hostRead more reviewsCleanliness:
lovely clean and comfortable home nestled in a residential community a 5 minute car drive to town
9. Exquisite oceanview gem
This home is a paradise because of its serene setting surrounded by panoramic ocean views. It has a 204.39 sq m (2,200 sq ft) mahogany deck, giving you plenty of space to gaze at the sea and enjoy the calming fresh air.
To kick it up a notch, pamper yourself with a soak in the sunken hot tub. The infinity pool is also a great space to hang out and admire the spectacular views. This swimming pool is heated for your comfort.
Accommodates: 10
Top guest reviews
Location:
amazing location across the street from gurney’sgreat property with excellent facilities in a great locationgreat place for friends and family tripRead more reviewsAmenities & Room:
gorgeous views from the home and pool deckbeautiful ocean views 5 minute walk to the beach nice hot tub / pool / deck clean housewe had a group of 5 adults stay there and we were very comfortable
10. High-end beach house
This stylish house offers family-friendly accommodation in Montauk. It has 371.61 sq m (4,000 sq ft) of living space with many child-friendly amenities. In the gourmet kitchen, you can enjoy preparing home-cooked meals. While you are busy cooking, the kids can enjoy playing in the backyard, especially on the swing set.
Stair gates are provided, and the swimming pool is fenced, so you need not worry about the safety of the young guests. If you are staying between Memorial Day weekend and October 1, you are welcome to use the swimming pool.
Accommodates: 8
Minimum Nights: 7
Refund Policy :
Top guest reviews
Host:
tabitha was extra helpfulit's mostly homeowners on the beach so we got to know some neighbors and everyone is friendlyplayground for kids and the house is very kids friendlyLocation:
the location was greatin any case the location is awesomethe house design and features including the close proximity to the beach make this house a perfect vacation spotRead more reviewsCleanliness:
the place is clean and perfect for four couplesvery clean plenty of space in a great locationthis space was extremely clean and i will definitely be back next seasonthe hot tub was fantastic and clean
Take a break and visit Montauk
Having a place to call home in Montauk is a huge deal, especially if you are coming for vacation. Indulge yourself and check out these vacation rentals with a private pool in Montauk, New York!
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