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

Amazing Home w. Pool + Basketball Court on 3 Acres
The house was so gorgeous and comfortable! Warm kitchen, beautiful spaces to lounge, luxurious bathrooms, and spacious bedrooms. We felt very at home. And Dylan was very responsive. We had an overly exciting exit from the house due to snowy conditions and he raced over to help salt the driveway. Highly recommend a stay at his house — I can’t wait to come back in the summer and use the pool!

4 BD w/ Heated Pool in E Hampton, Fully Furnished
We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.

Quaint Chalet w/Salt-heated Pool
Wonderful weekend stay. Charming.

Home in Bellport Village w Pool
Very clean and confortable place a few minutes from the center of the village. Both bedrooms have king beds which is always a plus! Large yard and deck

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend
Mike is a great host with helpful recommendations and plenty of advice. The house is amazing. Well located, calm, clean and so convenient. The pool is huge and very deep. Everything is perfect. Felt like at home. We will be back

Charming split level w/ heated pool & hot tub
Great place to spend time with family. Lots to do without the need to go out. The kitchen is well stocked with everything one needs to cook for the family.

East Hampton Oasis - Pool and Hot Tub
Tim is hands down the most responsive host we’ve ever dealt with through Airbnb. He was communicative, helpful and caring. We loved our experience and will be back!!!

Hope Haven
I was in Dion’s place with my family we really enjoyed the time we spent there,everything was perfect the pool was something that my kids enjoyed a lot, and hopefully we will come back again, for sure I totally recommend his house if you want to go and have a couple days of fun and relax thank you again Dion.
Condo rentals with a pool

Cherry Grove 1 bedroom condo w/heated pool!
Great place, exactly as advertised. Terrific location near ferry dock (making arrival/check-in extremely easy and fast, which was a relief after a long trip to get to Fire Island), near the little main hub of Cherry Grove… minutes or less to the general store, restaurants, bars. 5 minute walk to the beach. Although there is some bar noise at night, the unit is well sound-insulated. Hosts extremely friendly and communicative, full of info and recommendations. They take pride in their place and in being great hosts. Cozy place with very good value for Fire Island. The pool was a nice plus - salt water pool, lit at night. Met some of the other residents in the building who were extremely friendly and fun. Bed was very comfy. We slept in a lot. Wi-Fi worked perfectly. Nice desk in the bedroom for the few times work called. Roku TV. Lots of board games Bedroom has AC which worked great. Beach chairs and towels included. Coin laundry on site worked well. Great value. Would definitely return!

Cliffside Resort Poolside Condo A204
Everything was just perfect! Just what I expected. Expect the best when you book here. They're worth every penny. Will return again.

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!

Seaside Summer Escape: 2BR Waterfront Condo w/Pool
We had an amazing stay! We stayed off peak season, although alot was closed we felt right at home and were more than happy to spend family time at this condo! The views were stunning, and the condo was immaculate. We were close to everything and was still within very reasonable driving distance to the surrounding towns. Julie was a pleasure to work with and was always very responsive and accomadating throughout the process. Hoping to stay again next year!

Beautiful Waterview Condo on the North Fork of LI
Such a beautiful condo by the water! Too bad we stayed in November, we would have enjoyed the terrace way more! Mia was so responsive and helpful with my questions prior to the weekend at her place.

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
The space is adorable, and we loved the history of the rental and the community. The location was perfect for us—close to everything and secluded all at the same time. Also Jeff is an amazing host and made us feel welcome/at home. The next time we have to head to NY for a family visit we will definitely try to stay here again.
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!!

Explore the Water & Woods at a Relaxing Retreat
We had an amazing time staying at this house! It was in a great location, well-stocked with everything we needed, and the host was incredibly responsive. The check-in process was seamless, making our stay even more enjoyable. My family and I had a wonderful experience, and we would definitely book again!

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 Remsenburg-Speonk
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ551 before taxes and fees
Total number of reviews
310 reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Beach
- Yale University
- Gilgo Beach
- Ocean Beach Park
- Dunewood
- Cooper's Beach, Southampton
- Quotonset Beach
- Robert Moses State Park
- Shinnecock Hills Golf Club
- Giants Neck Beach
- Woodmont Beach
- Walnut Public Beach
- Clinton Town Beach
- Bethpage State Park
- Seaside Beach
- Jennings Beach
- Amagansett Beach
- Copiague Beach
- Marvin Beach
- Attawan Beach
- Shennecossett Beach
- Sunken Meadow State Park
- Robert Moses State Park Field 2
- Connetquot River State Park Preserve