Vacation rentals with a pool in Long Island Sound

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Long Island Sound rentals with a pool

House rentals with a pool

Guest favorite
A saltwater pool features a vibrant blue surface and is surrounded by a spacious terrace. Sun loungers are positioned along the poolside, and a fenced area provides safety. Lush greenery creates a serene backdrop, enhancing the outdoor space for relaxation.
Home in Woodbury
4.94 out of 5 average rating, 18 reviews

2 homes in one (in-law design) w/salt water pool

ChristineRating, 5 stars7 months ago
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!
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!
Top guest favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
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.
Guest favorite
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh
4.83 out of 5 average rating, 81 reviews

Entire Home (private pool), Event Friendly

ChannyRating, 5 stars2 weeks ago
Faisal was extremely responsive throughout our stay. we loved the indoor pool and the game tables. there was a nice selection. The rooms were nice. It was great that the bedrooms were on the same floor as the living room, dining room and kitchen. We came with an elderly person and they were able to make their way around the house. my son asked if he can use the fire pit out in back and he was able to. he collected wood from the side of the house. nice location. we really enjoyed our stay.
Guest favorite
An outdoor swimming pool is surrounded by a spacious stone patio, featuring six lounge chairs in vibrant colors. Lush greenery and trees border the area, creating a private setting. The pool reflects the clear sky above, inviting for a refreshing swim.
Home in Kingston
4.83 out of 5 average rating, 70 reviews

Beaver | Pool, Firepit, Secluded, 10 acres

GraemeRating, 5 stars2 months ago
We had an absolutely wonderful stay at Hava’s Airbnb! From the moment we booked, Hava was an incredible host—warm, welcoming, and unbelievably reachable. She responded to every question we had almost instantly, whether it was about check-in details or local recommendations, making the entire experience seamless and stress-free. The place itself was spotless, cozy, and exactly as described, with thoughtful touches that made us feel right at home. Hava’s communication stood out—she checked in to ensure everything was perfect without ever being intrusive. Her suggestions for nearby spots were spot-on, and it’s clear she genuinely cares about her guests’ comfort. We couldn’t have asked for a better host, and we’d love to stay here again. Highly recommend Hava to anyone looking for a fantastic Airbnb experience!
Top guest favorite
A single-story house is depicted, featuring a light exterior complemented by solar panels on the roof. The front yard showcases well-maintained greenery, with blooming shrubs adding bursts of color. A clear blue sky serves as a backdrop, enhancing the home's inviting appearance.
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 Manorville
4.98 out of 5 average rating, 252 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

JennineRating, 5 stars1 week ago
Our family had an amazing stay at this location. Loved that all the switches were clearly labeled as we have had trouble figuring out lighting in other locations. What a great touch! Wonderful yard and the basement was fun for all ages. This location was perfect for us as we have family all over the island. Lots of stores locally for anything you need. Highly recommend!
Superhost
Home in Southampton
4.91 out of 5 average rating, 45 reviews

New Southampton mega home with heated gunite pool!

SamuelRating, 5 stars3 months ago
Great place to stay and great host !

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
The vibrant exterior of The Appalachian building is showcased, featuring colorful wooden siding and multiple balconies. A sparkling outdoor pool is visible in the foreground, surrounded by lounge chairs and shaded by umbrellas. Lush greenery lines the area, contributing to a welcoming environment.
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
A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.
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
A large outdoor swimming pool is surrounded by lounge chairs and several umbrellas. The water is clear and appears inviting, reflecting sunlight. A portion of the condo building with multiple levels is visible in the background, framed by trees.
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
The exterior of The Appalachian Lodge is displayed, showcasing a multi-story building with a combination of warm colors and architectural details. A heated outdoor pool and lounging area are visible in the foreground, surrounded by landscaped grounds and comfortable seating options.
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
A tranquil outdoor pool area is surrounded by a spacious deck featuring lounge chairs. A white pergola is positioned nearby, with shaded seating available. The clear water of the pool reflects the serene landscaping and blue sky, creating a relaxing environment.
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
The image showcases a multi-story condo building set amidst neatly trimmed hedges. Sun loungers and patio umbrellas are positioned around a seasonal pool, which can be seen in the foreground. The design features white balconies and large windows, contributing to a light and airy appearance.
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
The studio features a queen-sized bed adorned with a floral-patterned blanket. A comfortable sofa and armchair are positioned nearby, along with a small table. Natural light filters through a nearby door, illuminating the warm wood flooring.
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

Top guest favorite
An outdoor seating area features a cozy sectional sofa with decorative cushions, a fire pit table at the center, and a large umbrella offering shade. Lush ferns are positioned around the space, while the surrounding trees create a natural backdrop.
Home in Rhinebeck
5 out of 5 average rating, 71 reviews

Rhinebeck Country Living with a Modern Twist

YetundeRating, 5 stars4 months ago
Beto and Scott are amazing host! From the complimentary wine to ensuring that we were comfortable by checking in, I couldn't ask for more. My family and I are truly appreciative to have experienced our stay in their home during the holidays. If you're considering renting this, please do (especially in the summer). No complaints!
Top guest favorite
A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.
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!
Superhost
A spacious deck features a swim spa surrounded by potted plants and outdoor furniture. The farmhouse with white siding is visible in the background, alongside a scenic view of hills and greenery under a clear blue sky.
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviews

Private Catskills Retreat | Hot Tub, Sauna & Tipi

ChrisRating, 5 stars16 months ago
We had a lovely time at Healing Waters Farm. Great location close to Belleayre Mountain. The place itself has everything you need, well stocked kitchen, and lovely clean bathrooms. The property has a calming stream, large swimming hot tub and sauna which we our family enjoyed. Recommend highly for a peaceful getaway.
Guest favorite
The heated in-ground swimming pool is surrounded by lush flowering landscaping, featuring vibrant blue hydrangeas. On the pool deck, several chaises and a shaded seating area offer a space for relaxation, complemented by the tranquility of the private, wooded surroundings.
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!!
Guest favorite
A quaint stone structure is surrounded by lush greenery and manicured shrubs. Climbing vines cover part of the exterior, contributing to a natural aesthetic. Soft grass and ornamental plants create a serene outdoor setting, inviting exploration and interaction with nature.
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.

Destinations to explore