
Holiday rentals with a pool in Amagansett
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Top-rated rentals with a pool in Amagansett
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Popular amenities for Amagansett rentals with a pool
House rentals with a pool

Close to Everything! Family Friendly
Upon seeing her home on the website, I contacted Amy several months prior to my travel days. She responded right away, answered what questions I had, and the booking was set. About a month prior to my check in date I asked to come a day early and she easily accommodated me. I received check in instruction a day or two prior to my arrival. On check in day after a long flight and drive from the airport I contacted Amy from the car asking for any suggestions for dinner prior to reaching her home. She got back to me immediately with a couple of places. It's a beautiful home, lush surroundings and a large pool. There was a notebook with information about the home and check out instructions. I can't give a high enough recommendation!

Gorgeous East Hampton Getaway
Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.

Stylish+Modern Cape w/Saltwater Pool-5min to Beach
Great spot in Hampton Bays! The house was as described and in a very cute and walkable neighborhood. Super close drive to the beach and a couple of local restaurants and eateries. Loved how private the spot felt too! David’s done a wonderful job with the backyard, so you get the comfort of having close neighbors without the intrusiveness. Pool was awesome. We definitely enjoyed it!

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!

Spacious Village Fringe East Hampton Home W/ Pool
Perfect house, exactly what we needed and so close to everything. Will definitely come again! Also Dan was an amazing host and super responsive and helpful!

Walk to East Hampton Village & Ocean Beaches
Ed was a great, communicative host, and the place was cozy for four of us during a week-long work trip!

Bright & Modern E Hampton Getaway w/ Pool & Spa
Our stay at the property was truly exceptional!! Rob was highly accommodating, ensuring that every aspect of our visit was seamless from check-in to check-out. The hot tub and the fire place were definitely our favorite. Highly recommend!

Beautiful House
I felt Welcomed! The place was warm and beautiful. Clean and had everything and more in the kitchen!!! Extremely responsive and caring for all and any needs or requests I had. I highly recommend this place. Great location and very accommodating. Loved staying there!! I cannot express my gratitude enough!!
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

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+

Beachside Waterview 2Br Condo w/ Pool in Greenport
We had a great stay! Instructions were clear and the home had everything we needed.

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
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!!
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.
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 Amagansett
Total rentals
230 properties
Nightly prices starting at
$232 AUD before taxes and fees
Total number of reviews
2.7K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with dedicated workspaces
120 properties have a dedicated workspace
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- Beach
- Charlestown Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- Shinnecock Hills Golf Club
- Point Judith Country Club
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Silver Sands Beach
- Quotonset Beach
- Ninigret Beach
- Outer Beach at Smith Point County Park
- Groton Long Point South Beach
- Cedar Beach
- South Jamesport Beach
- Groton Long Point Main Beach
- Clinton Town Beach
- Mystic Seaport Museum
- Bayview Beach