Vacation rentals with a pool in Long Island

Find and book unique homes with a pool on Airbnb

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Popular amenities for Long Island rentals with a pool

House rentals with a pool

Guest favorite
Home in East Hampton
4.88 out of 5 average rating, 107 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

IanRating, 5 stars1 month ago
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.
Top guest favorite
Home in Warwick
4.98 out of 5 average rating, 61 reviews

4 bedroom house with pool (Kids & Dog Friendly)

MichelleRating, 5 stars4 days ago
Betty was so quick to help when our original location to stay was cancelled. I am so thankful her property was available and how easy she made the process after what we went through!
Superhost
Home in East Hampton
4.88 out of 5 average rating, 109 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

BrittanyRating, 5 stars8 months ago
The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!
Top guest favorite
Home in Cheshire
5 out of 5 average rating, 133 reviews

Pool House

EllenRating, 5 stars2 weeks ago
Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.
Superhost
Home in East Hampton
4.83 out of 5 average rating, 95 reviews

East Hampton Oasis - Pool and Hot Tub

KevynRating, 5 stars1 month ago
Tim is hands down the most responsive host we’ve ever dealt with through Airbnb. He was communicative, helpful and caring. We loved our experience and will be back!!!
Top guest favorite
Home in Shirley
5 out of 5 average rating, 16 reviews

Hope Haven

HilarioRating, 5 stars8 months ago
I was in Dion’s place with my family we really enjoyed the time we spent there,everything was perfect the pool was something that my kids enjoyed a lot, and hopefully we will come back again, for sure I totally recommend his house if you want to go and have a couple days of fun and relax thank you again Dion.
Guest favorite
Home in Bridgehampton
4.76 out of 5 average rating, 38 reviews

Cheerful 3 bed-3bath beach cottage home with pool

JillRating, 5 stars3 months ago
Had a great weekend. We felt right at home and comfortable. Close to town and winery’s.
Superhost
Home in Rocky Point
4.96 out of 5 average rating, 100 reviews

Luxury modern farmhouse with heated pool & hot tub

StephanieRating, 5 stars1 month ago
Kerry’s place was absolutely STUNNING! I mean truly breathtaking. The place was squeaky clean and had plenty of room for my group of 6. You can tell that Kerry put a lot of love and thought into everything. Although we didn’t have kids on this trip, I soooo appreciate that there were kid plates, a crib and even baby detergent; how thoughtful!! Do not hesitate to stay here; you will truly feel at home!!!! Kerry, you rock!

Condo rentals with a pool

Superhost
Condo in Vernon Township
4.79 out of 5 average rating, 123 reviews

Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

JasonRating, 5 stars1 week ago
Henry’s place was exactly as described . The place was clean and perfect for 2 people. I would recommend staying there again.
Top guest favorite
Condo in Vernon Township
4.96 out of 5 average rating, 165 reviews

One bedroom condo at Mountain Creek Resort

MelissaRating, 5 stars2 months ago
We really enjoyed our stay! The condo was VERY clean, full stocked with all of the needed essentials and in a great location right by the ski slope. Both the bed and pull-out coach were SUPER comfortable. All instructions were super clear, and the recommendations were perfect. Thank you for letting us stay at your place, we love Mountain Creek!
Superhost
Condo in Greenport
4.84 out of 5 average rating, 129 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

DanielleRating, 5 stars3 weeks ago
We had an amazing stay! We stayed off peak season, although alot was closed we felt right at home and were more than happy to spend family time at this condo! The views were stunning, and the condo was immaculate. We were close to everything and was still within very reasonable driving distance to the surrounding towns. Julie was a pleasure to work with and was always very responsive and accomadating throughout the process. Hoping to stay again next year!
Top guest favorite
Condo in Montauk
5 out of 5 average rating, 222 reviews

Montauk Waterfront Condo w/ Sunset Views

MollyRating, 5 stars1 week ago
Absolutely wonderful stay and host. I've stayed at dozens of Airbnbs and this is one of my favorites! Doug's place is even better in person than the photos. We were a little nervous taking our first trip away with our baby, but it was extremely clean and comfortable, and Doug was so kind and responsive. The condo complex has a lovely boardwalk for taking walks, and the deck furniture was so comfortable to lounge in and take in the beautiful view. We hope to be back!
Guest favorite
Condo in Vernon Township
4.94 out of 5 average rating, 837 reviews

Appalachian Lodge Top Floor w/views

Jahari LeeRating, 5 stars1 week ago
My children and I had a wonderful time! The unit was immaculate, the views were lovely, and there was plenty to do at the hotel. Paul was the best host! We had a car issue and had to extend our stay. He was polite, quick to respond, accommodating, and he took excellent care of us whenever we had any questions or concerns. We are looking forward to visiting again!
Top guest favorite
Condo in Norwich
4.98 out of 5 average rating, 135 reviews

The Vacay Villa

JamieRating, 5 stars1 week ago
Krista place is very clean and welcoming. It had perfect personal touches. From coffee creamer for our morning coffee, to shower essentials. I find the small personal touches so nice and it is welcoming. Christa offered east check in and extended my check out time with no questions ask. This was a very nice place for a weekend trip and we will def be booking again!
Guest favorite
Condo in Greenport
4.92 out of 5 average rating, 138 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

RoxanaRating, 5 stars6 months ago
The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.
Guest favorite
Condo in Montauk
4.83 out of 5 average rating, 176 reviews

Coastline View Studio

DylanRating, 5 stars6 months ago
This was absolutely perfect for our wedding weekend in Montauk. We were so close to everything which made it very convenient. The room was perfect and loved the clothing rack perk! Everything was clean and loved the skylights in the unit and the patio overlooking the water. 10/10 woud definitely stay here again!

Home rentals with a private pool

Guest favorite
Home in East Hampton
4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

LynnRating, 5 stars6 months ago
Beautiful home worked perfect for our wedding visit. Loved sitting on the deck! Beautiful landscaping and very private! We were very confortable and able to relax between events and visit. Donna wad very flexible and allowed us to enter early so a dew of our family members could do s little remote eork. I hope to rent here again in the future! As a special surprise we saw the northern lights from the deck one night!!
Top guest favorite
Home in East Hampton
4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

JulianaRating, 5 stars7 months ago
We had an amazing time staying at this house! It was in a great location, well-stocked with everything we needed, and the host was incredibly responsive. The check-in process was seamless, making our stay even more enjoyable. My family and I had a wonderful experience, and we would definitely book again!
Guest favorite
Home in Southampton
4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars7 months ago
One could not ask for a better hosts than Christina and Phil - they are extremely communitive, proactive and helpful. Their house is beautiful - gourmet kitchen, in-ceiling speakers throughout the house, nice deck, pool and a picturesque location. The master bedroom has access to the back deck and a great shower. We had all three bedrooms full and everyone enjoyed their stay. We did not take advantage of the kitchen, but if we come back to the Hamptons we would stay here for longer and cook some meals. We are art collectors, so definitely appreciated the works Christina & Phil have amassed. The one thing I would bring to the attention of future renters is that you definitely know you are in somebody else's home - this is the first time we have unpacked only to find that every drawer was full, so we had to place stuff on top of the dresser or on the few open shelves in the closet. That said - totally worth it and would definitely recommend this Airbnb. Hope to be back soon!
Home in East Hampton
5 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

KatieRating, 5 stars34 months ago
Mike’s place made for the perfect Hamptons vacation. The location was the perfect starting point for day trips to Montauk and the harbors and we enjoyed the short walk to the beach daily… but there really is no need to leave this amazing property. Our family cannot stop raving about the amazing outdoor setup that we took full advantage of every day. Mike was very responsive and provided a detailed guide for the house and excellent recommendations for the area. We would 100% book again when we’re in the area and would recommend this place to anyone looking for an amazing Hamptons experience.

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