Vacation rentals with a pool in Wainscott

Find and book unique homes with a pool on Airbnb

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Popular amenities for Wainscott rentals with a pool

House rentals with a pool

Superhost

Home in Hampton Bays

4.78 out of 5 average rating, 99 reviews

Jacuzzi & pool. Fenced in property.

SarahRating, 5 stars4 weeks ago
A great place to stay! Very enjoyable!
Guest favorite

Home in East Hampton

4.87 out of 5 average rating, 103 reviews

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

KathrynRating, 5 stars2 weeks ago
I stayed at Ashton's place by myself on a visit to see my parents, who also live in Springs. It was everything I could have hoped for. So peaceful, and such a beautiful space. Amazing high ceilings and natural light. The yard is gorgeous, so I can only imagine how lovely it is when the weather is warm. Ashton himself is very responsive and accommodating. I was sad to leave!
Guest favorite

Home in East Hampton

4.87 out of 5 average rating, 38 reviews

Clearwater Beach Oasis -4 Bds 3 Bth & Pool

BridgetRating, 5 stars6 months ago
My group of 4 loved this house in EH Springs. We were out east for a long weekend for a wedding, 4 adults. The pool is huge, the backyard had plenty of room to spread out, and there were plenty of supplies for outside (cushions, towels, etc). The bedrooms were comfortable and spotless, as were the bathrooms and kitchen. Dariusz and Patricia left us a really nice welcome gift (wine, snacks, a cake!) and a handwritten card. We felt very welcome - every detail was thought of - the house was fully stocked with coffee, condiments, lots to get us started when we arrived. We agree with other reviewers - while the pictures here are accurate, they don't do the house justice!! I really hope to come back :)
Superhost

Home in Southampton

4.72 out of 5 average rating, 36 reviews

Renovated Southampton Mega Home w pool and Jacuzzi

JessicaRating, 5 stars2 months ago
Ronnie was such an amazing and attentive host. The house was gorgeous and beyond our expectations. We had a wonderful time and are super grateful for Ronnie’s home and hospitality for our family get together.
Superhost

Home in East Hampton

4.83 out of 5 average rating, 92 reviews

East Hampton Oasis - Pool and Hot Tub

DavidRating, 5 stars3 months ago
Tim was a great host! My brother came into town earlier than expected and Tim let him put his luggage in the back of the house until check in. During the first day of our stay, our toilet wasnt functioning correctly and Tim had a plumber within the hour after I told him about the issue. Also, my niece left her jacket in the house after we checked out and I asked Tim if he could ship the jacket and I would pay for shipping. Tim not only shipped the jacket but he insisted on paying for the shipping and sent me the tracking info. If I am in the Hamptons again, I would definitely stay at Tim's again! It's a shame that it was off season and the pool was closed because it looked like it could be a lot of fun! I highly recommend this Airbnb if your planning on staying in East Hampton!
Guest favorite

Home in Montauk

5 out of 5 average rating, 20 reviews

MTK Designer House with huge fireplaces!

MineRating, 5 stars2 months ago
We had an amazing stay at Alissa and Danny’s house! The location is perfect—convenient to everything we needed, yet peaceful and relaxing. The house is carefully designed with families in mind, especially with kids. It has everything you could possibly need for young children, from toys to safety features, making it so easy to enjoy our time there. We were so impressed that we’ve already booked again for our next trip! Highly recommend for any family looking for a comfortable, family-friendly! Mine Gur
Guest favorite

Home in East Hampton

4.86 out of 5 average rating, 49 reviews

Spacious Village Fringe East Hampton Home W/ Pool

AprilRating, 5 stars4 months ago
Amazing host and great property! Had an amazing time - thank you Daniel!!
Guest favorite

Home in Bridgehampton

4.76 out of 5 average rating, 37 reviews

Cheerful 3 bed-3bath beach cottage home with pool

DianaRating, 5 stars1 month ago
Dang was a fabulous host and incredibly responsive. The home is lovely, spotless, bright, comfortable and located on a quiet street. Thank you, Dang!

Condo rentals with a pool

Guest favorite

Condo in Montauk

4.92 out of 5 average rating, 26 reviews

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

MarielRating, 5 stars4 weeks 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!
Superhost

Condo in North Fork

4.83 out of 5 average rating, 125 reviews

Seaside Escape w Pool, Private Beach + Patio

ShirleyRating, 5 stars2 months ago
Lovely stay in greenport! Short drive from major north fork activities. Can imagine its even better during the busy season!
Guest favorite

Condo in Montauk

5 out of 5 average rating, 217 reviews

Montauk Waterfront Condo w/ Sunset Views

ErinRating, 5 stars1 month ago
This place was perfect! It looks exactly like the pictures and was perfectly clean inside. Doug was always responsive for any questions we had. We couldn’t have asked for a better place to spend the weekend. Would definitely come back and stay again
Superhost

Condo in Hampton Bays

4.78 out of 5 average rating, 23 reviews

Waterfront Elevated Bungalow - Spectacular Views

SteveRating, 5 stars52 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

Condo in Montauk

4.89 out of 5 average rating, 9 reviews

Endless Summer Studio Condo w Balcony Bayview

StephenRating, 5 stars17 months ago
We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.
Guest favorite

Condo in North Fork

5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

KaitlinRating, 5 stars5 months ago
Overall relaxing stay and trip to Greenport. Sherri is very communicative and her instructions and listing is clear and accurate. The condo is well decorated and clean and has everything you need for a nice weekend. One thing to note- we were aware check in is between 3 and 5 pm based on the listing (wound up being around 4) but it would be nice for it to be earlier. Still 5 stars though!
Superhost

Condo in Hampton Bays

4.95 out of 5 average rating, 42 reviews

A Unique Piece of Paradise, Water Front pool

ElysiaRating, 5 stars5 months ago
We really enjoyed our stay. The unit was just enough space for my husband and I and our two daughters. Having a kitchen to prepare quick breakfasts in the morning before heading out for the day and having the pool and beach in the late afternoons gave us everything we needed to start and end busy days at the Hamptons Classic or visiting family. We are hopeful to visit again!
Guest favorite

Condo in Montauk

4.95 out of 5 average rating, 119 reviews

Deluxe Studio Apt@The Montauk Manor

ChristinRating, 5 stars4 months ago
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

Guest favorite

Home in East Hampton

4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

JulianaRating, 5 stars4 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!

Home in East Hampton

4.77 out of 5 average rating, 74 reviews

5br / 5ba; Bike to town and beach; Heated Pool

HillaryRating, 5 stars9 months ago
My family and I had the most perfect time. My daughter was over the moon with the kids play area in the basement and the toys! The entire house was gorgeous. Everything we were looking for. Everett was extremely responsive and allowed us to check out an hour later and check in an hour earlier. The pool was just perfect for us too! We definitely would stay here again!!
Guest favorite

Home in Water Mill

4.92 out of 5 average rating, 125 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

BillRating, 5 stars1 month ago
Lovely place, great for having friends and family for a home cooked meal
Guest favorite

Home in Southampton

5 out of 5 average rating, 81 reviews

Best of Country and Beach Living

DavidRating, 5 stars5 months ago
My family had a great stay. Mary Ann was sweet and helpful. Very comfortable home with tons of amenities that we enjoyed. The kids really liked helping to feed the chickens and all the natural wild life at the property. Highly recommend for family or groups.
Guest favorite

Home in East Hampton

4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

LynnRating, 5 stars3 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

Home in Southampton

4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars4 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!

Home in East Hampton

5 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

KatieRating, 5 stars31 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.
Guest favorite

Home in Sag Harbor

4.99 out of 5 average rating, 75 reviews

Luxurious All-Season Oasis close to Sag Harbor Village

NicholasRating, 5 stars1 month ago
This home was exceptional for our family trip. Lots of space, well equipped kitchen, a fantastic back yard, and every amenity you could want. The proximity to Sag Harbor is also great- it's an easy walk, which we made multiple times per day. Would absolutely stay here again someday.

Quick stats about vacation rentals with a pool in Wainscott

  • Total rentals

    250 properties

  • Nightly prices starting at

    ﺩ.ﺇ588 before taxes and fees

  • Total number of reviews

    2.8K reviews

  • Family-friendly rentals

    230 properties are a good fit for families

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

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