Vacation rentals with a pool in Wainscott

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Popular amenities for Wainscott rentals with a pool

House rentals with a pool

Superhost
Home in Hampton Bays
4.79 out of 5 average rating, 103 reviews

Private completely fenced in property. Near beach.

KarenRating, 5 stars2 weeks ago
This is a beautifully furnished large home with lots of extras, including very well outfitted gym, hot tub and pool (although the pool was not open yet during our visit). The backyard is huge and our dogs loved it. All of the bedroom are spacious and well appointed. It is a great entertaining house or a family with kids. We loved and in fact have already re-booked it for another visit!
Guest favorite
Home in East Hampton
4.88 out of 5 average rating, 106 reviews

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

IanRating, 5 stars2 days 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.
Top 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 stars8 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 East Hampton
4.83 out of 5 average rating, 94 reviews

East Hampton Oasis - Pool and Hot Tub

JocelynRating, 5 stars1 month ago
Tim’s place was great. The space was exactly as described and depicted. Peaceful location where I felt secluded, but was still located very close to the outside world. Tim was always responsive, provided clear instructions and stayed in touch without being intrusive. would definitely recommend! :)
Top guest favorite
Home in Shirley
5 out of 5 average rating, 16 reviews

Hope Haven

HilarioRating, 5 stars7 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.
Top guest favorite
Home in Montauk
5 out of 5 average rating, 20 reviews

MTK Designer House with huge fireplaces!

MineRating, 5 stars4 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 stars6 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, 38 reviews

Cheerful 3 bed-3bath beach cottage home with pool

JillRating, 5 stars2 months ago
Had a great weekend. We felt right at home and comfortable. Close to town and winery’s.

Condo rentals with a pool

Superhost
Condo in Montauk
5 out of 5 average rating, 12 reviews

Second Floor Corner Unit Overlooking the Ocean

VishnuRating, 5 stars5 months ago
A brief stay but a great stay. It was offseason but we got lucky with sunny October weather. The stay was less than a 5 minute drive from the main village with tons of shops, cafes, etc.. the room itself had a beautiful ocean view and was very clean and comfy. Nice shower, comfy beds, plenty of linens and towels provided. Parking included. Overall a very nice stay.
Guest favorite
Condo in Montauk
4.93 out of 5 average rating, 27 reviews

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

MarielRating, 5 stars3 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!
Superhost
Condo in North Fork
4.83 out of 5 average rating, 126 reviews

Oceanfront Condo – Incredible Spring Rates!

ShirleyRating, 5 stars4 months ago
Lovely stay in greenport! Short drive from major north fork activities. Can imagine its even better during the busy season!
Top guest favorite
Condo in Montauk
5 out of 5 average rating, 221 reviews

Montauk Waterfront Condo w/ Sunset Views

PatriciaRating, 5 stars6 days ago
Comfy, clean and peaceful. Would definitely go back.
Top guest favorite
Condo in North Fork
5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

KaitlinRating, 5 stars7 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!
Condo in Hampton Bays
4.95 out of 5 average rating, 42 reviews

A Unique Piece of Paradise, Water Front pool

ElysiaRating, 5 stars7 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 North Fork
4.92 out of 5 average rating, 137 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

MariaRating, 5 stars5 months ago
Irinas place was exactly as she described. She answered all inquiries in a timely manner. We will definitely be back.
Top guest favorite
Condo in Montauk
4.95 out of 5 average rating, 119 reviews

Deluxe Studio Apt@The Montauk Manor

ChristinRating, 5 stars6 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
4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

LynnRating, 5 stars5 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
Home in East Hampton
4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

JulianaRating, 5 stars6 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
Home in Southampton
4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars6 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 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 Wainscott

  • Total rentals

    240 properties

  • Nightly prices starting at

    ﺩ.ﺇ624 before taxes and fees

  • Total number of reviews

    2.7K 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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