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Holiday rentals with a pool in Hampton Bays

Find and book unique homes with a pool on Airbnb

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Popular amenities for Hampton Bays rentals with a pool

House rentals with a pool

Guest favourite
Home in North Fork
5 out of 5 average rating, 35 reviews

North Fork paradise between beaches and vineyards

AndrewRating, 5 stars5 months ago
We had a lovely stay at Karine’s cute house! The kitchen was very nicely outfitted, beds were super comfortable, and the big wood-burning fireplace was excellent! We appreciated all the cool artwork around the house, and Karine’s wonderful photography book! We got to enjoy lots of bird life, and we were lucky to have a bit of snow. What a beautiful and peaceful spot. We can’t wait to come back in warmer weather to enjoy the pool and lovely big deck and yard!
Guest favourite
Home in Hampton Bays
4.93 out of 5 average rating, 14 reviews

Chic Hamptons Hideaway: Beach Bungalow w/ Pool

SuzanneRating, 5 stars1 month ago
Alexander’s place was the perfect jumping off point for a week of adventuring through the Hamptons! The house is gorgeous and well equipped, and communication with the host was excellent. We had a complete blast! Most of all we enjoyed the local food! We especially loved several neighborhood restaurants—Rumba, Out of the Blue, Black Sheep bagels and Cowfish were all big hits with our crew. We’ll be back!
Superhost
Home in East Hampton
4.84 out of 5 average rating, 100 reviews

East Hampton Oasis - Pool and Hot Tub

MaryRating, 5 stars1 week ago
We had the most beautiful weekend stay at Tim’s home! Everything is accurately described and the pool and hot tub were amazing!! All the beds were very comfortable. Was perfect for a 5 girl weekend getaway!! Tim was incredibly communicative and checking in was a breeze. The location is PERFECT in East Hampton!! So many amazing restaurants and bars nearby. 100% will stay here again for my next Hamptons trip. Thank you so much Tim!!
Guest favourite
Home in Hampton Bays
4.95 out of 5 average rating, 21 reviews

Cozy Modern 3-Bedroom

LauraRating, 5 stars10 months ago
Chloe has such a beautiful home! Really a wonderful find! Highly recommend :)
Guest favourite
Home in Sag Harbor
4.86 out of 5 average rating, 268 reviews

Exclusive Sag Harbor Compound

Amy RoseRating, 5 stars2 weeks ago
Ben is a super host. His home is absolutely beautiful and well managed. His thoughtful recommendations and well timed check ins and reminders were the height of polished professionalism. We felt right at home, down to the bins of toys in the living room that our toddler and baby played with every day.
Guest favourite
Home in East Hampton
4.93 out of 5 average rating, 153 reviews

Large heated pool, games room, near private beach

KarlaRating, 5 stars2 weeks ago
A beautiful house to always spend time with important people.
Guest favourite
Home in Eastport
5 out of 5 average rating, 11 reviews

Summer Out East

JoshuaRating, 5 stars5 months ago
My family and I had the most amazing time celebrating two birthdays as well as New Year’s. The pictures do not do this house justice. This house was so amazing for our family of nine. The beds were so comfortable, the rooms were very spacious, the two sunroom rooms were perfect (my family would hang out in the tiny sunroom with the bar in it every single morning. It was everyone’s favorite room.). One thing that was the best bonus was the built-in speaker system throughout the house on the main level. My brother-in-law is a DJ and knew how to use the system, which was amazing because we would have dance parties. The only thing I would ask Constantine to do is to possibly give instructions on how to use it because it is a definite bonus. We even had a bonfire one night as well as a BBQ. Even though we came during winter this place was perfect.
Superhost
Home in Hampton Bays
5 out of 5 average rating, 5 reviews

Bay Beach House: *New Pool, Hot Tub + Bikes

TomRating, 5 stars7 months ago
This is a beautiful small house . . . a real architectural gem, with its sunken main floor living and bedrooms on the wings. The hot tub is right out the sliding door from the dining area and guest bedroom, so it's smoothly reached in all weather, and the back patio and yard are a lovely private space. You're just off the peninsula from Southampton but it is easy to go to town without getting on Route 27, so you get the Hamptons lifestyle without the insane prices. Great value for a couple, a small family, or two couples who are close-knit.

Condo rentals with a pool

Superhost
Condo in Montauk
4.94 out of 5 average rating, 17 reviews

Second Floor Corner Unit Overlooking the Ocean

LaurenRating, 5 stars1 week ago
The Beach Plumb was lovely! Everything was as advertised. The distance to town and the beach, the spacious layout, and the amenities are among the things that made our stay great
Guest favourite
Condo in Montauk
4.89 out of 5 average rating, 28 reviews

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

MarielRating, 5 stars5 months ago
Mark's place was exactly what I was looking for to ring in the New Year in style, comfort and complete relaxation! I was able to start each day with a quiet cup of coffee and then head directly to the beach for a long morning walk (just a short drive away). Montauk Manor is an absolute hidden gem for a winter break and the indoor pool and hot tub are a rare find in the Hamptons. Check-in/out could not have been any easier and the Manor staff are wonderfully welcoming and friendly. There were still a good number of local shops open, including Left Hand Coffee. 100% recommend for all seasons and will eagerly book again!
Superhost
Condo in North Fork
4.85 out of 5 average rating, 136 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

SeanRating, 5 stars3 weeks ago
We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.
Top Guest favourite
Condo in Montauk
5 out of 5 average rating, 229 reviews

Montauk Waterfront Condo w/ Sunset Views

RachelRating, 5 stars1 week ago
We loved Montauk - low key, wild and upmarket at the same time. This apartment was perfect, super quiet yet near everything and loved seeing wild deer from the terrace
Superhost
Condo in Hampton Bays
4.78 out of 5 average rating, 23 reviews

Waterfront Elevated Bungalow - Spectacular Views

SteveRating, 5 stars56 months ago
If we don't give a good review, can we keep this to ourselves?! Patti was a perfect host; the views were fantastic, whether from the outdoor porch or inside through the French doors looking out on the water. Access to the small beach and pool were excellent and we were close to several good restaurants (many of which Patti suggested, including some on the water) for take-out during the pandemic. Wifi was great and everything was very clean and as advertised. We generally fly for vacations and long weekends but had to stay closer to home this year and this was a perfect choice.
Superhost
Condo in Bridgehampton
4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

StaceyRating, 5 stars9 months ago
Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+
Guest favourite
Condo in Mount Sinai
5 out of 5 average rating, 34 reviews

1856 Trading House close to water

JohnRating, 5 stars5 months ago
Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.
Guest favourite
Condo in North Fork
4.92 out of 5 average rating, 139 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

MorganRating, 5 stars3 weeks ago
We had a great stay! Instructions were clear and the home had everything we needed.

Home rentals with a private pool

Superhost
Home in East Hampton
4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

LarryRating, 5 stars48 months ago
House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.
Guest favourite
Bungalow in East Hampton
4.93 out of 5 average rating, 108 reviews

East Hampton Ranch with Access to Clearwater Private Beach

KateRating, 5 stars8 months ago
We had a wonderful stay at Peter's home. It was beautifully decorated, very comfortable and a quick drive to Springs. Access to the private clearwater beach was a plus! Thank you for sharing your beautiful home with us.
Top Guest favourite
Home in East Hampton
4.98 out of 5 average rating, 130 reviews

Explore the Water & Woods at a Relaxing Retreat

LaelRating, 5 stars1 month ago
Absolutely beautiful home and wonderful experience!! The host was quick to respond and the amenities were excellent. There was zero lack! Would definitely return for another stay!
Guest favourite
Home in East Hampton
4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

LynnRating, 5 stars8 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 favourite
Home in Southampton
4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars8 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 stars35 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.

Quick stats about holiday rentals with a pool in Hampton Bays

  • Total rentals

    320 properties

  • Nightly prices starting at

    $201 AUD before taxes and fees

  • Total number of reviews

    5.5K reviews

  • Family-friendly rentals

    280 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

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