
Holiday rentals with a pool in Southampton
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Southampton
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Popular amenities for Southampton rentals with a pool
House rentals with a pool

North Fork paradise between beaches and vineyards
Spent a long weekend here with one other couple and had an amazing first trip to the North Fork. Karine's home was beautiful and close to everything we wanted to see, and her recommendations were excellent and super helpful! I hope to come back soon and would absolutely recommend this place to others. Thank you Karine!

Designer Home w/ Heated, Salt-Water Pool
Great spot. Easy to get to places. Comfortable. Great backyard + pool. We had a good time, zero complaints here. We are a family of 3 and found everything convenient.

Modern East Hampton Home w/ Heated Saltwater Pool
Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.

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!

Wooded Oasis and Guest House in Hamptons!
We enjoyed a lovely stay in the beautiful home. Josh was easy to reach and flexible with our requests.

Secluded Farmhouse - Studio Apartment Style Unit
This is a beautiful farmhouse setting with gorgeous gardens, chickens, a nice screened in private porch, and a very friendly and adorable kitty. Jessica was a great host and provided some delicious homemade yogurt with milk and fruit, and plenty of coffee and tea. We brought our dog and he was comfortable there, we had plenty of space to walk him around.

Beach House Feel - newly renovated backyard Oasis
Christine's place was nice and clean! We especially loved the fire pit and the pool. Upon arrival of the AirBNB Christine was waiting to meet us and show us around. This was something that was new to me in my AirBNB experience, but it was honestly so nice and so was she! Christine let me know that I could communicate with her for anything that was needed and asked for recommendations to make her place better. This place was so well-equipped, close to everything and it comfortably fit me and my 6 other friends! I would definitely book again with Christine.
Apartment 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+

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!
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
Jessica’s home was absolutely beautiful! We had an amazing, relaxing weekend and felt right at home :) Jessica is an amazing host - absolutely recommend staying here!!!!
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 Southampton
Total rentals
370 properties
Nightly prices starting at
₹864 before taxes and fees
Total number of reviews
5K reviews
Family-friendly rentals
320 properties are a good fit for families
Pet-friendly rentals
170 properties allow pets
Rentals with dedicated workspaces
220 properties have a dedicated workspace
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- Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- Robert Moses State Park
- Shinnecock Hills Golf Club
- Walnut Public Beach
- Ocean Beach Park
- Dunewood
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Seaside Beach
- Jennings Beach
- Silver Sands Beach
- Quotonset Beach
- Robert Moses State Park Field 2
- Heckscher State Park
- Sunken Meadow State Park
- Outer Beach at Smith Point County Park
- Groton Long Point South Beach