
Holiday rentals with a pool in Hampton Bays
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Hampton Bays
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Hampton Bays rentals with a pool
House rentals with a pool

North Fork paradise between beaches and vineyards
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!

Chic Hamptons Hideaway: Beach Bungalow w/ Pool
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!

East Hampton Oasis - Pool and Hot Tub
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!!

Cozy Modern 3-Bedroom
Chloe has such a beautiful home! Really a wonderful find! Highly recommend :)

Exclusive Sag Harbor Compound
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.

Large heated pool, games room, near private beach
A beautiful house to always spend time with important people.

Summer Out East
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.

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

Second Floor Corner Unit Overlooking the Ocean
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

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

Seaside Summer Escape: 2BR Waterfront Condo w/Pool
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.

Montauk Waterfront Condo w/ Sunset Views
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

Waterfront Elevated Bungalow - Spectacular Views
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.

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath
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+

1856 Trading House close to water
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.

Beachside Waterview 2Br Condo w/ Pool in Greenport
We had a great stay! Instructions were clear and the home had everything we needed.
Home rentals with a private pool
Walk to Water. Stunning Home with Gorgeous Pool & Grounds.
House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.
East Hampton Ranch with Access to Clearwater Private Beach
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.

Explore the Water & Woods at a Relaxing Retreat
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!
Enchanting Home with Large Decks and Heated Pool
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!!
Perfect Getaway at Sunny Modern Shampton Lake House
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!
Saltbox with Separate Poolhouse in Northwest Woods
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
Destinations to explore
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Boston Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Apartment rentals Hampton Bays
- Family-friendly rentals Hampton Bays
- Rentals with a kayak Hampton Bays
- Pet-friendly rentals Hampton Bays
- Rentals with breakfast Hampton Bays
- Beach house rentals Hampton Bays
- Waterfront rentals Hampton Bays
- Rentals with lake access Hampton Bays
- Beachfront rentals Hampton Bays
- Rentals with a fireplace Hampton Bays
- House rentals Hampton Bays
- Rentals with a fire pit Hampton Bays
- Rentals with a washing machine and dryer Hampton Bays
- Fitness-friendly rentals Hampton Bays
- Rentals with a patio Hampton Bays
- Kid-friendly rentals Hampton Bays
- Rentals with a hot tub Hampton Bays
- Cottage rentals Hampton Bays
- Rentals with outdoor seating Hampton Bays
- Condo rentals Hampton Bays
- Rentals with beach access Hampton Bays
- Rentals with an EV charger Hampton Bays
- Rentals with pools Suffolk County
- Rentals with pools New York
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Gilgo Beach
- Cooper's Beach, Southampton
- Napeague Beach
- Robert Moses State Park
- Shinnecock Hills Golf Club
- Walnut Public Beach
- Ocean Beach Park
- Dunewood
- Bethpage State Park
- Woodmont Beach
- Amagansett Beach
- Amityville Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Quotonset Beach
- Robert Moses State Park Field 2
- Heckscher State Park
- Sunken Meadow State Park
- Calf Pasture Beach