Long Island, the longest and largest island in the contiguous USA, is a summer retreat for the upper crust. Some of the mansions of bygone eras are now museums that you can visit. It is a place where your taste buds tingle with a feast of good wine and delectable oysters. Long Island’s Atlantic front has sandbars and little islands with stunning beaches. Spend time swimming, surfing, fishing, and taking lessons in beachside trapeze. Make time for crossing Great South Bay embayment to Fire Island. There, behold the wondrous Sunken Forest, a rare assemblage of trees and plants. Long Island’s top-echelon vacation rentals offer a warm welcome home wherever your travels take you. But are you looking for a place with a pool? If so, then find out the best Airbnbs with pool in Long Island, New York.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 11, 2024.
1. Family friendly country home with outdoor pool (from USD 750)
This farmhouse in Riverhead offers stylish quarters and 1.00 acre (0.40 hectare) of manicured grounds. Guests have exclusive use of essential amenities along with a travel crib, children’s dinnerware, and an assortment of toys. After putting your bags down, you can head to the deck and check out the open space.
The glittering pool water beckons from the neat and sunny yard. Guests booked from May 1 to October will be able to use this amenity. The Olympic-sized pool is available for swimming and pool games 24/7. Make it a centerpiece of relaxing days and nights spent on Long Island.
Top guest reviews
Amenities & Room:
annie’s place was perfect the pool and yard were the ultimate vacation relaxationthe pool was a hit for our family- so beautiful and the perfect temperaturebeautiful home and setting gorgeous pool and backyardthe pool and backyard were amazing and very relaxingCleanliness:
the house was clean and well stockedthe house was beautiful and very cleanthe house was clean and welcoming and felt very secluded even on a residential streetHost:
annie was an excellent hostannie was an excellent hostshe is a great host and very responsiveannie was helpful and communicative tooannie- thank you again for being a great hostRead more reviewsLocation:
the location is great because it is close to so many great activitiesthis house does not disappoint the location is perfect if you are seeking privacy and relaxationthe location is also central to wine country and easily accessible to south hampton/montauk activitiesannie’s house was wonderful - very well decorated comfortable and in a great locationgood location with quick access to both north and south shores
Superhost
2. The Good Vibez House (from USD 628)
Spend your time in a ranch-style smart home with an eye-catching mural. It is a unique and modern property with cozy nooks, a dedicated workstation, and fast Internet. This is a year-round getaway in the heart of Long Island.
The spacious poolside is an oasis with a firepit, four hammocks, and a lounge area with a TV set. You can use the five-burner barbecue grill and spread a feast on the outdoor dining table. You may use the fire pit for a gooey dessert of roasted marshmallows. The host provides the firewood and s'more kits to get you started.
Top guest reviews
Cleanliness:
it was clean and so well designedthe living room is so clean and well equippedwe had a great stay - the place was spotless and everything was very comfortablethe pool is wide and cleanthis airbnb was a 10/10 would definitely recommend quiet area clean house & very welcomingHost:
great house really nice hostduane and eva are super hostgreat place with great hostduane is a great host with excellent host as very responsive understanding and accommodatingseriously these hosts thought of everything the smart home features were so coolRead more reviewsLocation:
quiet neighborhood and very comfortable house
3. Charming guest suite with pool and garden deck (from USD 165)
This air-conditioned accommodation is spread out on two levels. Cooks will be stationed in the first-floor kitchen. The living room, dining area, and laundry facilities are on the first floor as well. Bedrooms are upstairs along with the full bath. If you are dressing up for dinner, there is an iron and iron board on hand.
This Airbnb is a secondary unit attached to the main building - a private suite where guests have access to a pool and furnished deck. The pool area is surrounded by greenery and is an ideal spot to unwind and take Instagrammable selfies.
Top guest reviews
Amenities & Room:
the backyard is beautiful we often sat outside to enjoy the view while we ate breakfastbeautiful home with all the amenities gorgeous back yard area with pool off street parking highly recommendwe took advantage of the pool a lot and enjoyed having breakfast on the patioCleanliness:
felt like a clean and safe staya great staycation spot clean spacious and privatethe entire place was clean (which made us feel safe given the times right now)Read more reviewsLocation:
the neighborhood was fairly quiet and felt very safethis place is the perfect spot if you are visiting the huntington/woodbury area
4. Bohemian sanctuary next door to a restaurant
Here is a retreat like no other in Long Island. You find everything in order plus bonus features to level up your holiday. The indoor pool and hot tub are yours to enjoy day and night. The indoor pool can be heated for a surcharge per night. Guests are also welcome to use the sauna.
The interiors of this Airbnb are colorful but no less relaxing. You can make savory and sweet treats in the updated and stocked kitchen. You can hang the apron on some days and enjoy the offerings of the next-door restaurant, Sag Harbor which is a local landmark.
Sag Harbor, New York, United States
33.45 km (20.8 mi) from Splish Splash Water ParkAccommodates: 5
Top guest reviews
Amenities & Room:
the yard is fully fenced and huge so our dog had plenty of room to runCleanliness:
the house was very clean upon arrivalHost:
her care takers were also great taking care of everything even leaving us fresh eggs every morningnicole is a wonderful hostnicole was a great hostone of the kindest airbnb hosts out there and the house is stunningthe fully fenced spacious yard and dog-friendly property was the bonus that sealed the dealRead more reviewsLocation:
the home is central to many great restaurants and shopping
5. Classic beauty at the waterfont (from USD 1000)
What is the ideal getaway for a second honeymoon? How about a lovely home from the 1930s? This luxurious Airbnb has a roomy and verdant backyard. The structure and design epitomize grace and class. It is the only brick home in the community. To one side of the property are the waters of Patchogue Bay.
Incredible views make it worthwhile to stay on the upper deck. You can also enjoy romantic sunsets by the poolside on the front part of the house. The pool is closed in the wintertime but is back in business when spring comes. If you wish for the pool to be heated, inform the host in advance and settle the additional charge.
Top guest reviews
Amenities & Room:
the beds and furniture are comfortablethe amenities are great and we definitely love the pool and balconyevery bedroom and bathroom are decorated beautifully with top knotch amenities (baths showers etc)even on a hot day the fans make it incredibly comfortablethe rooms had splendid views and the house was exceedingly comfortableCleanliness:
everything was very clean and beautifully decoratedplace was very clean and kitchen was stockedit was spotlessly clean beautifully decorated and well stocked with everything we neededthis house is amazing it is very clean and has plenty of space and securityall of the bedrooms kitchen and bathrooms were impeccably cleanHost:
she is an excellent hostthe host was excellent and very responsive to all of our questionsthe host responds quickly and is very niceelizabeth is a great host who resonds quickly if you have any questions or issuesyou can certainly tell she takes pride in her home as well as being a hostRead more reviewsLocation:
beautiful house in a stunning location on the waterthis would be a great location for a family tripperfection this place is perfectthe location was terrific as we were only 3 miles from the beautiful little town of bellportelizabeth’s place was a great location to spend the weekend
6. Charming family nook in the Hamptons (from USD 900)
This renovated ranch is garbed beautifully in nautical themes. It is a stocked and furnished vacation retreat with a spacious green lawn. The rest of the fenced yard is occupied by a wood-burning fire pit and swimming pool.
The wood-burning fire pit is surrounded by sturdy chairs. A few steps from the fire pit are a line of sun loungers and a well-maintained pool. The pool is open from Memorial Day onward. If your idea of a getaway is munching on grilled favorites and suntanning on the poolside, then book this place in the Hamptons today.
Top guest reviews
Amenities & Room:
the pool and lounge chairs offered hours of funthe pool and outdoor space was both tranquil and fun for the entire familythe backyard space was perfect with beautiful landscaping a large pool and a firepitit’s a huge back yard and a great table to eat out with an umbrellawe really enjoyed the pool grilling and the firepitCleanliness:
modern homey comfy clean great communication from hostessthe house is very clean and well stockedthe pool is amazing clean and well-maintainedwe found the house to be very clean and comfortablethe house was clean modern spacious and well equippedHost:
she was beyond helpfulgreat host and propertybut the owners were even bettershe was very responsive and welcoming into her homethe host was very responsive and friendlyRead more reviewsLocation:
a lovely place in a great locationthe neighborhood is quiet and prettygreat location near many good restaurants and west of the worst of the hamptons trafficwe enjoyed our stay at christine’s placethe pebble beach close by was also a fun excursion
7. Pet-friendly basement apartment (from USD 90)
This pet-friendly basement apartment boasts a full-sized home theater with surround sound. If you are not much of a film aficionado, you can spend time in the expansive garden instead.
The back patio of this Airbnb is a quiet place to hang out. There is an outdoor grill ready to be fired up for a steak lunch. Best of all, there is a shared pool and sun loungers. The pool area is bordered by greenery as the property is in a wooded area. You may inquire during booking if the pool is available during your stay.
Top guest reviews
Amenities & Room:
the best part was having access to the outdoor grill and the pool spacevery comfortable space with a ton of little touches (ie: take out menus coffee tea muffins extra toothbrushes etc)the room was clean the bed comfortable outstanding big screen tv with roku netflix hbo go cablethe bed and linens were super the pillows wonderfulthe tv is huge and they provide cable netflix and other streamingCleanliness:
the space was very cleansuper clean and very comfortableeverything was super clean and organizedspacious warm very clean and tidygaby's place was very clean and well keptHost:
great host who cares about the guestoutstanding host and a lovely apartmentthe host gaby was kind and welcomingwhat a charming studio apartment and friendly hosts made me feel right at homeboth are really friendly peopleRead more reviewsLocation:
lovely location and settinggreat location and close to food and other storesfantastic location right in the heart of stony brookdowntown stony brook is walking distance and very cutegreat stay in three village area close to stony brook
8. Hamptons home with heated outdoor pool (from USD 1191)
Here is a resort-like designer home with landscaped grounds and a seasonal, heated pool. After sunning on the poolside or swimming a few laps, you can saunter in the shade of crepe myrtles and among French lavender blooms. This stylish Airbnb boasts natural hardwood flooring and French doors. Your family pet is welcome to the house and grounds once approved by the host.
The pool is available from May 15th to September 15th. Heating cost is courtesy of the host from Memorial Day to Labor Day only. If the swimming pool is is available and you prefer the water heated outside of that period, then be ready to shell out 250 USD per day for it.
Top guest reviews
Amenities & Room:
great outdoor space and comfortable bedsi look forward to returning in the warmer months to take advantage of the poolthe pool house offered two bedrooms and bath so it was like having two houses on the same propertythe place was fabulously from the indoor gym to the great jacuzzi type tubs to its pristine kitchenthe design makes every corner a treat to notice-truly the bed was extremely comfortableCleanliness:
clean and well decoratedhe keeps his property clean and well appointedvery clean place very beautiful homewell appointed clean and very comfortablechris's place was great clean stylish and comfortableHost:
the owner is also highly responsivechris lives up to his super host statusgorgeous home host was extremely helpful and accommodations were comfortablehe was a great host thanks chrishost very responsive to textsRead more reviewsLocation:
awesome location close to everythingit is also perfectly located very close to sag harborbeautiful home great location to beach wineries and quaint little town square for shopping and great foodbed is very comfortable close to vineyard3 minute drive from wolffer close to town of bridgehampton great weekend destination
9. Charming cottage with seasonal pool (from USD 425)
This Airbnb offers guests a seasonal above-ground swimming pool, one side of which abuts a wooden deck with sun loungers. The pool occupies one part of the spacious yard. When the pool is closed, guests can still worship the sun on the Adirondack deck chairs and hammock.
Instead of bringing a car to Long Island, bring a boat instead. The marina is only two houses away from this property. A stock of tents, beach chairs, and umbrellas is available for guests to use. There are also beach bikes on the property. Moreover, the host can help you find a jet ski, kayak, and paddleboard rental outfit nearby.
Top guest reviews
Amenities & Room:
there were even amenities in the bathrooms like shampoo soap and conditionerin the back yard there are several nice chairs to visit on and an above ground poolthe pool is very nice and the outdoor area with the grill was wonderful for having a cookoutthe pool and pool deck was an added bonus for usbeds were comfortable the kitchen well stocked with all the pots pans dishware etc that you’d needCleanliness:
everything was clean and beds were comfortableclean and spacious space with fabulous outdoor seatingspace was clean and it was easy to find everythinghouse was very cleanwe enjoyed this modest yet clean and comfortable homeHost:
joan was a great host and communicatorjoan was a lovely host and very quick to respond to our questions as we planned our tripowner was honest and helpful in her communicationthe pool is perfect hosts are very friendly and responsivejoan was an excellent host from start to finish always responsive and accommodatingRead more reviewsLocation:
great location and charming areaperfect location re hampton beachesa great place to relax close to beach and close to winerieswe loved the convenience of the location on a quiet streetit’s about 18-25 mins to southamptons so it’s pretty close to where everything is
10. Summerfield (from USD 332)
Take a short ferry ride from New York to Shelter Island and spend a grand holiday in this palatial getaway. This Airbnb is not a typical vacation home. It has not one but three ensuite master bedrooms. It also has a movie theater. You won’t run out of diversions in the game room. The grounds are gorgeous to behold from every deck in the property.
The different wings of the house are connected by walkways. It may take a day or two to master the layout. You’d be happy to extend your vacation because this great house also has a hot tub and a heated gunite outdoor pool. The pool is exclusive to guests. Start making plans for poolside games and your favorite version of water volleyball.
Top guest reviews
Amenities & Room:
we loved the view from the living room that looked out onto the deckgorgeous home with incredible backyard filled with gorgeous pool hot tub deck putting green and large grass-filled yardmy family loved the large dining tables that allowed us all to sit together for mealsi'm sure the huge pool would be a treat in the summerthe room is so large and most couples enjoy the extra spaceCleanliness:
very clean and responsive host communicationhouse was very clean and spaciousit was spotless and even more gorgeous in personthe home was exactly as advertised and was very cleanincredibly beautiful & clean home perfectly laid out for large families and lots of different common areas to hangHost:
puja was a lovely hostshe was a great host overall and made sure our group enjoyed all aspects of our staypuja is an amazing hostpuja was an excellent host and was quick to respond to any questions during our staypuja was responsive and an amazing hostRead more reviewsLocation:
we preferred it due to the easy access to the kitchen and being close to the fireplacelastly great location close to beaches the supermarket and the state parkshelter island is a great destination and this house is within close reach of it allpuja’ place was a perfect hide-away on shelter island
Spend a deluxe holiday in Long Island
Long Island is synonymous with opulent summer retreats and remarkable coastal attractions. Make your next holiday a time to splurge, relax, and visit Long Island’s tourist hotspots. Better yet, make your next holiday a time spent with loved ones in a top resort-style Airbnb in Long Island.
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