Vacation rentals with a pool in Remsenburg-Speonk

Find and book unique homes with a pool on Airbnb

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Popular amenities for Remsenburg-Speonk rentals with a pool

House rentals with a pool

Guest favorite
Home in Weston
4.93 out of 5 average rating, 15 reviews

Amazing Home w. Pool + Basketball Court on 3 Acres

EmmaRating, 5 stars3 months ago
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!
Guest favorite
A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.
Home in East Hampton
4.88 out of 5 average rating, 107 reviews

4 BD w/ Heated Pool in E Hampton, Fully Furnished

IanRating, 5 stars4 weeks ago
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.
Guest favorite
A heated saltwater pool is surrounded by a stone patio, featuring lounge chairs and sun umbrellas. Lush greenery and landscaping enhance the serene atmosphere. Pool floats are visible in the water, inviting relaxation and leisure.
Home in North Fork
4.89 out of 5 average rating, 9 reviews

Quaint Chalet w/Salt-heated Pool

VaughnRating, 5 stars6 months ago
Wonderful weekend stay. Charming.
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, 11 reviews

Home in Bellport Village w Pool

GuillaumeRating, 5 stars1 week ago
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
Superhost
Home in East Hampton
4.74 out of 5 average rating, 89 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

AntoineRating, 5 stars7 months ago
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
Superhost
A relaxing outdoor space features a heated in-ground pool surrounded by brick patio. Lounge chairs are positioned along the edge, while a shaded area is provided by an umbrella. Lush greenery and decorative fencing frame the area, creating a serene environment.
Home in Hampton Bays
4.83 out of 5 average rating, 36 reviews

Charming split level w/ heated pool & hot tub

MarciaRating, 5 stars7 months ago
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.
Superhost
An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.
Home in East Hampton
4.83 out of 5 average rating, 95 reviews

East Hampton Oasis - Pool and Hot Tub

KevynRating, 5 stars1 month ago
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!!!
Top guest favorite
A single-story house is depicted, featuring a light exterior complemented by solar panels on the roof. The front yard showcases well-maintained greenery, with blooming shrubs adding bursts of color. A clear blue sky serves as a backdrop, enhancing the home's inviting appearance.
Home in Shirley
5 out of 5 average rating, 16 reviews

Hope Haven

HilarioRating, 5 stars8 months ago
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

A shared heated pool is framed by a wooden deck, with two stories of accommodations visible in the background. Flower pots hang from the balcony, and several chairs are positioned around the pool area, creating a welcoming outdoor space.
Condo in Cherry Grove
5 out of 5 average rating, 3 reviews

Cherry Grove 1 bedroom condo w/heated pool!

RobertRating, 5 stars8 months ago
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!
A heated swimming pool is surrounded by lounge chairs and umbrellas, with multiple access steps leading into the inviting, clear blue water. In the background, a two-story building features private balconies overlooking the pool area.
Condo in North Fork
4.94 out of 5 average rating, 16 reviews

Cliffside Resort Poolside Condo A204

JoyRating, 5 stars9 months ago
Everything was just perfect! Just what I expected. Expect the best when you book here. They're worth every penny. Will return again.
Guest favorite
A well-maintained heated pool is surrounded by lounge chairs and shaded tables. Umbrellas provide shelter over the seating areas. A club house is visible in the background, complementing the inviting outdoor space designed for relaxation.
Condo in North Fork
4.84 out of 5 average rating, 106 reviews

Beautiful condo on Long Islands Northfolk

LauraRating, 5 stars2 days ago
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!
Superhost
A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.
Condo in North Fork
4.84 out of 5 average rating, 129 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

DanielleRating, 5 stars3 weeks ago
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!
Guest favorite
A well-maintained heated pool is surrounded by lounge chairs arranged on a paved deck. The pool reflects the evening sky, while nearby tables and grilling areas invite relaxation. The condominium buildings, featuring multiple balconies, are positioned in the background.
Condo in North Fork
4.89 out of 5 average rating, 149 reviews

Beautiful Waterview Condo on the North Fork of LI

AnnaRating, 5 stars5 months ago
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.
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 Hampton Bays
4.78 out of 5 average rating, 23 reviews

Waterfront Elevated Bungalow - Spectacular Views

SteveRating, 5 stars55 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 Bridgehampton
4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

StaceyRating, 5 stars7 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, 33 reviews

1856 Trading House close to water

JulieRating, 5 stars4 months ago
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

Guest favorite
A wooden bench with blue cushions is situated beside a heated pool, surrounded by colorful flowering plants in blue pots. Lush greenery forms a natural backdrop, enhancing the outdoor space.
Home in East Hampton
4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

LynnRating, 5 stars6 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!!
Top guest favorite
A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.
Home in East Hampton
4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

JulianaRating, 5 stars7 months ago
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!
Guest favorite
A serene freshwater lake is surrounded by lush greenery, reflecting clear blue skies and clouds above. A wooden dock extends into the water, providing a space for relaxation and enjoyment of the tranquil setting.
Home in Southampton
4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars7 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 bright and airy living space is enhanced by large windows allowing natural light to flood in. A comfortable sectional sofa and accent chairs provide seating, while a stylish coffee table with books sits in the center. A dining area is visible in the background.
Home in East Hampton
5 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

KatieRating, 5 stars33 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

    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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