
Vacation rentals with a pool in Water Mill
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Top-rated rentals with a pool in Water Mill
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Popular amenities for Water Mill rentals with a pool
House rentals with a pool

Spectacular Southampton Retreat!
Daniel’s home was absolutely wonderful. Myself and my guests felt right at home, and we enjoyed every amenity of the home. His communication was great, and we would be happy to stay again with him/his property!

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna
We rented Nick’s place for a long overdue weekend of friends getting together from different bits of the world. The house is conveniently 1hr45mins from JFK and an easy drive from the city. The house was very spacious and perfect for a long weekend. Nick was very responsive and truly went above and beyond trying to get the pool working off season for us. The property is about a 10min car ride from the Southampton Main Street with loads of good restaurants. We also really enjoyed the sauna. Thank you Nick!

4 BR Hamptons Oasis w/ Pool,Jacuzzi & Beach Access
Gorgeous house and property that is even better than the photos. Like other reviews have mentioned, the highway noise in the backyard is definitely present, but easy enough to ignore. Really enjoyed our stay and communication was great!

Renovated Southampton Shores pool, tennis, beach
Lovely place for a long weekend with family! The house was pristine, up to date, charming, and all the linens were fresh and clean. It was very well stocked with kitchen essentials and books and toys for kids. Location also prime with a private beach a 10 min walk away. The only minor issue we had was an issue with the pool heating (it being the 1st pool weekend of the year) but this was sorted out promptly. Would happily stay there again!

Beach House | Hot Tub & Fire Place | Sag Harbor
We had an amazing stay at this property. Everything was exactly as noted in the listing. Rooms were extremely spacious. The house was beautifully decorated. The yard is great for just relaxing with some friends. I would definitely love to stay here again and would recommend it to anyone looking to stay in Sag Harbor.

Charming Village home in the heart of Southampton
An ideal location in Southampton, Lori’s house is clean, cozy and peaceful; we thoroughly enjoyed spending our New Years there!

Secluded Luxury: New Gunite Pool, Walk to Bay
Dewey’s place is such a dream! Everything is freshly renovated and just feels so crisp, clean, and stylish. You can tell so much love went into the design it’s the perfect mix of modern and cozy. We felt right at home the second we walked in. The kitchen is gorgeous, the bathrooms are spa-like, and every little detail was just so well thought out. Dewey was the sweetest host super responsive and made everything totally seamless. The location is amazing too quiet and peaceful, but still close to all the fun spots (beach, town, restaurants). We didn’t want to leave! Already planning our next trip back. If you’re thinking about booking, do it you’ll love it just as much as we did!

Private East Hampton Estate
We had a great time at Mark’s place! The backyard was quiet and beautiful - it was the perfect relaxing weekend for our group. We’d love to stay here again!
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!

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+

Seaside Summer Escape –2BR Waterfront Condo w/Pool
We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!

Deluxe Studio Apt@The Montauk Manor
Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!

Beautiful Condo on the Ocean Bluffs
You can not beat this location - quiet private beach right across the street, nice pool and about a 20 minute walk to town or super short car ride. The place is clean, as pictured and John was great to deal with. Will definitely be back!
Home rentals with a private pool
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 vacation rentals with a pool in Water Mill
Total rentals
210 properties
Nightly prices starting at
ﺩ.ﺇ698 before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with dedicated workspaces
140 properties have a dedicated workspace
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- Shinnecock Hills Golf Club
- Walnut Public Beach
- Ocean Beach Park
- Dunewood
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Quotonset Beach
- Heckscher State Park
- Ninigret Beach
- Sunken Meadow State Park
- Outer Beach at Smith Point County Park
- Groton Long Point South Beach