Vacation rentals with a pool in Remsenburg-Speonk

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Popular amenities for Remsenburg-Speonk rentals with a pool

House rentals with a pool

Guest favorite
A serene outdoor area features a brand new gunite pool surrounded by a spacious bluestone patio. Several lounge chairs are positioned along the poolside, with lush green grass and trees framing the backdrop of the setting.
Home in The Hamptons
4.89 out of 5 average rating, 36 reviews

Hamptons 3/2 - New Gunite Pool &Bluestone Patio

LaurenRating, 5 stars9 months ago
My friends and I had such a great visit at Sean's and would definitely visit again!
Superhost
An aerial view captures a spacious ranch-style home surrounded by lush greenery. A heated pool is outlined by a protective fence, with two shaded pergolas nearby. The manicured lawn invites outdoor relaxation, and a playset is visible on the left side of the image.
Home in The Hamptons
4.76 out of 5 average rating, 113 reviews

Private completely fenced in property. Near beach.

RuzinRating, 5 stars1 week ago
A fenced-in slice of Hamptons heaven where both dogs and humans roamed free and happy. It’s basically a resort if your resort includes wagging tails, wine within walking distance, and a private mini movie theater for when socializing gets… exhausting. Days were spent by pool , nights were hot tub therapy. 10/10 would trade city stress for this fenced paradise again.
Top guest favorite
The spacious backyard features a heated pool surrounded by sun beds and lounge chairs. A dining table is set nearby under a shaded area. Lush greenery and privacy fencing create a serene environment, enhancing the outdoor experience.
Home in Bellport
5 out of 5 average rating, 12 reviews

Home in Bellport Village w Pool

BarbaraRating, 5 stars2 weeks ago
We were in town for a baseball tournament. The place was in a great location, convenient to restaurants and the fields. The house was very quiet and comfortable for a family of 4. The pool looked nice but we didn’t get to use it due to colder weather and our schedule. The host responded quickly to our messages. Overall would recommend.
Guest favorite
The backyard features a spacious swimming pool set against a clear blue sky, surrounded by greenery. A deck overlooks the pool and offers seating areas for relaxation. The scene captures a serene outdoor atmosphere, perfect for leisurely days in the sun.
Home in The Hamptons
4.96 out of 5 average rating, 46 reviews

Hampton Hideaway: Pool, Bay View, Mins to Beach

PeggyRating, 5 stars5 months ago
We had an unforgettable family Christmas at this wonderful home! It was spacious, beautifully decorated, and had a cozy, welcoming atmosphere perfect for the holidays. The living area was ideal for gathering and the well-equipped kitchen made preparing Christmas dinner a breeze. The large dining table comfortably fit our entire family. The bedrooms were cozy and comfortable, ensuring everyone had a great night’s sleep, and the outdoor space was perfect. The peaceful location provided a relaxing retreat while still being close to local shops and activities. The hosts were fantastic—communication was clear, and they went above and beyond to make us feel at home. We couldn’t have asked for a better place to celebrate together. Highly recommend!
Guest favorite
A well-maintained backyard features a heated saltwater pool surrounded by lush greenery. Six lounge chairs are positioned alongside the pool, creating an inviting space for relaxation. The area is illuminated by gentle lighting, with a white fence providing a sense of privacy.
Home in The Hamptons
5 out of 5 average rating, 45 reviews

Hamptons Getaway/ Backyard OASIS/Monthly available

MichaelRating, 5 stars9 months ago
Great vacation…the house and pool were very enjoyable and relaxing. The pool was always heated, the host was always responsive and the area was close to some great restaurants and beaches. Thanks again
Superhost
A spacious outdoor area features a rectangular swimming pool, surrounded by a sun deck. Stairs lead up to a large deck connected to the architecturally designed house, which is flanked by tall trees providing a natural backdrop.
Home in The Hamptons
4.9 out of 5 average rating, 30 reviews

Bright Hamptons Getaway ☀️ Pool▪︎ Beach▪︎FamilyFun

CassandraRating, 5 stars3 weeks ago
we had a quiet girls getaway to celebrate my sister getting married-upon arrival we checked out the entirety of the home…to which we were pleasantly surprised every corner we turned! exquisite home with comfortable, aesthetically pleasing furnishing and so much gorgeous natural light. the outdoor shower was a huge BONUS! heated pool had us outside moving our bodies more than we’d imagined and was such a fun way to spend time together. the living room is so cozy and a great space to have a game-night-in! i could go on and on about each detail but you should simply stay here and enjoy for yourself all this property has to offer!
Top guest favorite
The backyard features a heated inground pool illuminated by soft lighting, surrounded by lush greenery. Two Adirondack chairs are positioned on the deck, inviting relaxation. The area is designed for comfort with wooden decking that complements the tranquil atmosphere.
Home in The Hamptons
5 out of 5 average rating, 38 reviews

Scenic Stay in Sparkling Home, Heated Pool 6bds

RhiannonRating, 5 stars2 weeks ago
I booked Jennifer’s listing for a girl’s weekend getaway with my friends and she went above and beyond with her communication, recommendations, and hospitality. She was quick to answer any questions I had and her house was beautiful, remote, and peaceful. Even though we didn’t have the best weather, we still were able to enjoy the beautiful backyard and heated pool, and the house was spacious enough for all 8 of us to stay comfortably! Overall we had a lovely stay in the Hamptons and will 100% be coming back! Thank you Jennifer!
Superhost
A charming cottage-style home is set amid lush greenery, featuring a covered porch with white railings. A gravel pathway leads to the entrance, surrounded by manicured shrubs and a well-kept lawn. The exterior is finished with natural wood siding and a sloped gray roof.
Home in The Hamptons
5 out of 5 average rating, 3 reviews

Hamptons Waterview Cottage

LisaRating, 5 stars9 months ago
This place is a gem! When we arrived the home was spotless and exactly as pictured. It seemed brand new and in excellent condition. The hosts were very kind and helpful and even gave us a bottle of wine and left bottled water in the fridge. The beds were so comfortable and the home was stocked with everything we needed. Our young kids loved swimming in the beautiful pool and we enjoyed exploring the rest of the picturesque property—so cool to see the wild turkeys walking around. We had a wonderful vacation and hope to return one day!

Condo rentals with a pool

Guest favorite
An expansive hallway features arched doorways and rustic wooden beams overhead. Potted plants add greenery, while large windows dressed with floral curtains allow natural light to illuminate the stone floor. Comfy seating arrangements are positioned along the walls, creating inviting spaces for relaxation.
Condo in The Hamptons
4.89 out of 5 average rating, 28 reviews

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

MarielRating, 5 stars5 months ago
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!
Top guest favorite
A large outdoor swimming pool is surrounded by lounge chairs and several umbrellas. The water is clear and appears inviting, reflecting sunlight. A portion of the condo building with multiple levels is visible in the background, framed by trees.
Condo in The Hamptons
5 out of 5 average rating, 228 reviews

Montauk Waterfront Condo w/ Sunset Views

MarieRating, 5 stars1 week ago
we had s great time staying at the apartment! it was way more spacious than we thought from the pictures, the balcony was amazing, you‘ll have sun through the whole day. Doug was a phenomenal host! We got their by LIRR and back with the hampton jitney. We rented two bikes in Montauk and it was amazing exploring the area by bike. Cannot recommend this area and the airbnb enough!
Superhost
A cozy living area is furnished with a beige sofa, a round wooden coffee table, and stylish light blue armchairs. A large window allows natural light to fill the space. Potted plants add a touch of greenery, creating a relaxed atmosphere.
Condo in Old Saybrook
4.89 out of 5 average rating, 73 reviews

Seashore getaway - CT shoreline

ScottRating, 5 stars2 weeks ago
Lauren was great and her home was exactly as promised! Great stay and will stay again!
Superhost
A bright and airy living space is highlighted by skylights and white wooden beams. A spacious kitchenette is situated behind a dining table surrounded by light chairs. Large windows invite natural light, and a television sits on a white console between soothing tones of gray and cream.
Condo in The Hamptons
4.78 out of 5 average rating, 23 reviews

Waterfront Elevated Bungalow - Spectacular Views

SteveRating, 5 stars56 months ago
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.
Superhost
A spacious outdoor pool area is framed by lush greenery and vibrant flowers. The rectangular pool is surrounded by a paved deck, with several lounge chairs positioned around it. A corner of the property includes a poolside storage shed, providing functional space.
Condo in The Hamptons
4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

StaceyRating, 5 stars8 months ago
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+
Guest favorite
Two people are seen swimming in a calm body of water, surrounded by gentle ripples reflecting sunlight. Lush greenery lines the distant shoreline, creating a serene backdrop against the shimmering surface.
Condo in Mount Sinai
5 out of 5 average rating, 34 reviews

1856 Trading House close to water

JohnRating, 5 stars5 months ago
Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.
Superhost
A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.
Condo in North Fork
4.9 out of 5 average rating, 125 reviews

Seaside Summer Escape –2BR Waterfront Condo w/Pool

DebbieRating, 5 stars3 weeks ago
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!
Guest favorite
The image showcases a multi-story condo building set amidst neatly trimmed hedges. Sun loungers and patio umbrellas are positioned around a seasonal pool, which can be seen in the foreground. The design features white balconies and large windows, contributing to a light and airy appearance.
Condo in North Fork
4.92 out of 5 average rating, 139 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

MorganRating, 5 stars2 weeks ago
We had a great stay! Instructions were clear and the home had everything we needed.

Home rentals with a private pool

Guest favorite
The exterior of a modern wooden house features a sloping roof and a welcoming front porch. Lush green grass surrounds the structure, complemented by small shrubbery thoughtfully arranged near the entrance. Three large windows provide natural light to the interior.
Bungalow in The Hamptons
4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

KateRating, 5 stars8 months ago
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.
Top guest favorite
Four lounge chairs are arranged under large umbrellas, providing shade beside a serene pool area. The colorful cushions on the chairs complement the lush green landscaping, which features diverse foliage and natural textures, enhancing the outdoor relaxation space.
Home in The Hamptons
4.98 out of 5 average rating, 130 reviews

Explore the Water & Woods at a Relaxing Retreat

LaelRating, 5 stars1 month ago
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!
Guest favorite
An inviting heated pool is surrounded by lush greenery and flowering landscaping. Comfortable loungers are positioned along the wooden deck, accompanied by a shaded umbrella. Steps lead from the poolside to a charming surrounding garden, offering a serene environment for relaxation.
Home in The Hamptons
4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

LynnRating, 5 stars8 months ago
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!!
Guest favorite
A spacious backyard is highlighted by a bright blue swimming pool, featuring a whimsical white swan float. Surrounding the pool are several lounge chairs and umbrellas, set against lush green hedges and trees that provide privacy.
Home in The Hamptons
4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars8 months ago
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!
A spacious deck is shown surrounding a large pool, with wooden flooring and colorful umbrellas providing shade. Comfortable outdoor couches with striped throws are positioned to face the pool, creating an inviting space for relaxation amid lush greenery.
Home in The Hamptons
5 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

KatieRating, 5 stars35 months ago
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

    G$31,382 GYD 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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