Holiday rentals with a pool in Greenport West

Find and book unique homes with a pool on Airbnb

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Popular amenities for Greenport West rentals with a pool

House rentals with a pool

Top guest favourite
Home in North Fork
4.97 out of 5 average rating, 206 reviews

Private Oasis W/Stunning Vinyard and Pool Views

RebeccaRating, 5 stars1 month ago
We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!
Superhost
Home in Hampton Bays
4.94 out of 5 average rating, 131 reviews

Peaceful Retreat in Immaculate Architect’s House

JessikahRating, 5 stars1 month ago
Michael’s place was amazing, means a few friends stayed this weekend for my birthday. He was always willing to help and very accommodating! The house itself is so beautiful and had everything we needed! It was our first time in The Hamptons and he gave us tons of recommendations!
Superhost
Home in East Hampton
4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

MariaRating, 5 stars1 month ago
Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.
Guest favourite
Home in North Fork
4.9 out of 5 average rating, 41 reviews

Gorgeous home with saltwater pool. Steps to beach!

michelleRating, 5 stars3 weeks ago
An amazing stay overall. It was comfortable for 6 adults. Spencer was extremely helpful throughout our stay — I had lots of questions and Spencer was quickly responsive. The house itself is beautiful and has that eastern Long Island charm. The backyard had lots of space and is well maintained alongside the pool. We also enjoyed a sunset evening at the beach which is just a few steps away. It was a wonderful weekend and I am certainly looking forward to staying here in the future!
Guest favourite
Home in Hampton Bays
4.97 out of 5 average rating, 60 reviews

4 BR Hamptons Oasis w/ Pool,Jacuzzi & Beach Access

MatthewRating, 5 stars1 month ago
Gorgeous house and property that is even better than the photos. Like other reviews have mentioned, the highway noise in the backyard is definitely present, but easy enough to ignore. Really enjoyed our stay and communication was great!
Top guest favourite
Home in Madison
5 out of 5 average rating, 37 reviews

Waterfront Beach House with pool

Andrew & HeatherRating, 5 stars1 week ago
Meaghan was a wonderful host who was very prompt, kind, and respectful of privacy. The house itself was stylish, comfortable, and modern while being kid friendly which is a tough thing to achieve in any home let alone an Airbnb. The view from the house was an absolute highlight! We had a great time!
Guest favourite
Home in Southampton
4.98 out of 5 average rating, 42 reviews

Renovated Southampton Home+Pool

GhitaRating, 5 stars3 weeks ago
We had a wonderful stay with my family! Everything went smoothly from start to finish. The check-in process was easy and communication was clear and prompt. Anisha and Rob are great host, very friendly and responsive. The space was exactly as described—clean, comfortable, and well-equipped with everything I needed for a relaxing stay. The house is spacious. I really appreciated how well the place was maintained. I would definitely stay here again and highly recommend it to anyone visiting Southampton!
Guest favourite
Home in East Hampton
4.84 out of 5 average rating, 32 reviews

Private East Hampton Estate

CloeRating, 5 stars2 weeks ago
We had a great time at Mark’s place! The backyard was quiet and beautiful - it was the perfect relaxing weekend for our group. We’d love to stay here again!

Apartment rentals with a pool

Superhost
Apartment in Montauk
4.94 out of 5 average rating, 17 reviews

Second Floor Corner Unit Overlooking the Ocean

LaurenRating, 5 stars1 week ago
The Beach Plumb was lovely! Everything was as advertised. The distance to town and the beach, the spacious layout, and the amenities are among the things that made our stay great
Guest favourite
Apartment in Montauk
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 favourite
Apartment in Montauk
5 out of 5 average rating, 229 reviews

Montauk Waterfront Condo w/ Sunset Views

RachelRating, 5 stars2 weeks ago
We loved Montauk - low key, wild and upmarket at the same time. This apartment was perfect, super quiet yet near everything and loved seeing wild deer from the terrace
Superhost
Apartment in Hampton Bays
4.78 out of 5 average rating, 23 reviews

Waterfront Elevated Bungalow - Spectacular Views

SteveRating, 5 stars57 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
Apartment in Old Saybrook Center
4.89 out of 5 average rating, 74 reviews

Seashore getaway - CT shoreline

RussellRating, 5 stars2 weeks ago
Lisa and I enjoyed our stay at Laurens place. Felt right at home. Very clean, open space. We had the best time and did not want to leave. We will be back for sure.
Superhost
Apartment in Bridgehampton
4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

StaceyRating, 5 stars9 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 favourite
Apartment 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.
Top guest favourite
Apartment in Montauk
4.95 out of 5 average rating, 120 reviews

Deluxe Studio Apt@The Montauk Manor

ChristinRating, 5 stars8 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 favourite
Bungalow in East Hampton
4.93 out of 5 average rating, 108 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 favourite
Home in East Hampton
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 favourite
Home in East Hampton
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 favourite
Home in Southampton
4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

ScottRating, 5 stars9 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 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 holiday rentals with a pool in Greenport West

  • Total rentals

    90 properties

  • Nightly prices starting at

    ₹10,388 before taxes and fees

  • Total number of reviews

    2.4K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

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