
Vacation rentals with a pool in Southold
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Southold
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Southold rentals with a pool
House rentals with a pool

Private pool/walk to beach; farms/vineyards abound
Staying at Amy's place was perfect for my friends and I while we're out on the North Fork for a wedding. Amy was very responsive with any questions we had. We were all very comfortable in the main living area as well as our bedrooms. The house was conveniently located to the wedding venue and my friends were also very happy that it was located near some pickleball courts. Thank you Amy for a wonderful stay.

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna
The house and gardens are beautiful. We enjoyed the outdoor deck with grill and pool, as well as the outdoor seating at a table with gas heating on it. Inside is wonderful, as well. Well equipped kitchen. Nicholas was very responsive and addressed our needs quickly.

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!

Ultimate House with Heated Pool, Hot Tub and Sauna
This Home was Amazing!! Anastasia is Phenomenal, I could see why they are Super Hosts. Their home is Beautiful and very clean. It’s filled with amenities! all that are in the description. So much so we didn’t even get a chance to take advantage of them all. We were only there for two days. Next time it’ll be much longer. I love this place!

Curated Artist Home with New Pool
I do not even know where to begin.We had a last minute change from our other booking and was completely stressed but Harris came in and saved the day with making it so easy for us to book his house last minute.From the minute we arrived to the personalized note with fresh flowers to having every product we needed in the bathrooms .The home was beautiful and very homey and enough space for all of our guests .The location was fantastic and we can’t wait to come back .Harris was the best host and my daughter had the best week .If you are looking for a fabulous house with a great location look no further .Harris ,we can’t thank you enough.We will definitely be back .

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!

Southampton Stunner: Pool, Beach & more!
This is the second time we've stayed at Veva's home and it will not be the last. The home is nestled beautifully in a quiet neighborhood. Sitting outside is tranquil and relaxing. The home is beautifully furnished and extremely clean & well maintained. It is private with ample space to park. In a matter of minutes, you can be in Sag Harbor for dinner, at the beach, or take a short drive to Montauk. The location is perfect for anyone looking to get away from the hustle and bustle of everyday life but still close enough to all the great locations and activities the Hamptons have to offer. We will be coming back for many years to come.

Renovated Southampton Home+Pool
We had a wonderful stay with my family! Everything went smoothly from start to finish. The check-in process was easy and communication was clear and prompt. Anisha and Rob are great host, very friendly and responsive. The space was exactly as described—clean, comfortable, and well-equipped with everything I needed for a relaxing stay. The house is spacious. I really appreciated how well the place was maintained. I would definitely stay here again and highly recommend it to anyone visiting Southampton!
Condo rentals with a pool

Cliffside Resort Poolside Condo A204
Very clean apartment! Easy check in/check out. Had a nice stay!

Water front, sunsets, sail boats, Wi-fi, birds
John and Cathy are amazing hosts. This was our second consecutive summer stay in their condo and it does not disappoint. The place and the amenities they provide are amazing and they are a wonderful couple who respects your privacy but are there for anything you need. I recommend anyone to stay here and know they would want to return. Thank you John and Cathy for making our second summer with you a fantastic vacation!

Bright and Airy One Bedroom Apartment in the Dunes
A fantastic place to stay in the Hamptons, a special gem of a place located in the Dunes of Amagansett, will be back every year!

Beautiful condo on Long Islands Northfolk
We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!

Beautiful Waterview Condo on the North Fork of LI
Great retreat for a long weekend. Enough space for family of four. Easy access to everything in the Greenport area. Mia was very responsive, and the place was great. We would stay here again!

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!
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 vacation rentals with a pool in Southold
Total rentals
90 properties
Nightly prices starting at
G$25,105 GYD before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 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
- TPC River Highlands
- Ocean Beach Park
- Dunewood
- Woodmont Beach
- Amagansett Beach
- Blue Shutters Beach
- Seaside Beach
- Jennings Beach
- Silver Sands Beach
- Quotonset Beach
- Heckscher State Park
- Ninigret Beach
- Sunken Meadow State Park
- Outer Beach at Smith Point County Park