Vacation rentals with a pool in Shirley

Find and book unique homes with a pool on Airbnb

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Popular amenities for Shirley rentals with a pool

House rentals with a pool

Guest favorite
Home in Westhampton Beach
4.97 out of 5 average rating, 76 reviews

Brand new house with an all year round hot tub.

JessicaRating, 5 stars4 weeks ago
Paula was great! The house was beautiful! Stayed here for my cousins wedding and we really enjoyed our stay!
Guest favorite
Home in Stamford
4.96 out of 5 average rating, 251 reviews

Midcentury Modern ZenHouse Sculptor Studio

EamonRating, 5 stars1 week ago
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.
Top guest favorite
Home in Manorville
4.93 out of 5 average rating, 29 reviews

Woodsy Retreat- Fireplace, HotTub, Private & Comfy

NicoleRating, 5 stars3 weeks ago
We love this house, this is our second time staying there & it holds a special place in our families heart, we had a house fire & this house made us feel at home, it is so homey & has everything you could possibly need & the hosts are amazing & dog lovers which we love! We hope to come back but to actually vacation and enjoy all the amenities of the beautiful pool, sauna and hot tub!
Guest favorite
Home in Bellport
5 out of 5 average rating, 27 reviews

Bellport Village Ranch, Saltwater Pool & Hot Tub

DanielleRating, 5 stars8 months ago
Paul is a great host. This is our 2nd time staying at Paul's home and it was just as wonderful as the first time. Clean, beautiful and in a lovely town. Paul is easy to communicate with and was thoughtful throughout the whole stay. We look forward to staying at Paul's home again in the future. Thanks Paul, for helping us with a wonderful weekend out east
Guest favorite
Home in North Fork
4.92 out of 5 average rating, 88 reviews

Modern farmhouse w/ pool, beach, horses and winery

XiuRating, 5 stars2 weeks ago
I had a wonderful stay! The place was exactly as described—clean, cozy, and well-equipped. The host was friendly and responsive, making check-in and check-out super easy. The neighborhood was quiet and convenient, perfect for relaxing after a day out. I would definitely stay here again and highly recommend it to anyone visiting the area!
Top guest favorite
Home in Hampton Bays
4.98 out of 5 average rating, 129 reviews

Beach House Feel - newly renovated backyard Oasis

JessRating, 5 stars1 week ago
Christine's place was nice and clean! We especially loved the fire pit and the pool. Upon arrival of the AirBNB Christine was waiting to meet us and show us around. This was something that was new to me in my AirBNB experience, but it was honestly so nice and so was she! Christine let me know that I could communicate with her for anything that was needed and asked for recommendations to make her place better. This place was so well-equipped, close to everything and it comfortably fit me and my 6 other friends! I would definitely book again with Christine.
Guest favorite
Home in East Hampton
5 out of 5 average rating, 23 reviews

Secluded Luxury: New Gunite Pool, Walk to Bay

KelliRating, 5 stars1 week ago
Dewey’s place is such a dream! Everything is freshly renovated and just feels so crisp, clean, and stylish. You can tell so much love went into the design it’s the perfect mix of modern and cozy. We felt right at home the second we walked in. The kitchen is gorgeous, the bathrooms are spa-like, and every little detail was just so well thought out. Dewey was the sweetest host super responsive and made everything totally seamless. The location is amazing too quiet and peaceful, but still close to all the fun spots (beach, town, restaurants). We didn’t want to leave! Already planning our next trip back. If you’re thinking about booking, do it you’ll love it just as much as we did!
Top guest favorite
Home in Hampton Bays
4.99 out of 5 average rating, 70 reviews

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

EmilyRating, 5 stars1 day ago
The most perfect place! It was a girls trip of 10 girls and the house was the perfect amount of space for us all and the house was spotless. There are restaurants, bars, and a coffee shop within walking distance which was a plus! Would definitely recommend!!

Condo rentals with a pool

Condo in North Fork
4.94 out of 5 average rating, 17 reviews

Cliffside Resort Poolside Condo A204

MichelleRating, 5 stars2 months ago
Very clean apartment! Easy check in/check out. Had a nice stay!
Condo in North Fork
5 out of 5 average rating, 6 reviews

Water front, sunsets, sail boats, Wi-fi, birds

CharlesRating, 5 stars9 months ago
John and Cathy are amazing hosts. This was our second consecutive summer stay in their condo and it does not disappoint. The place and the amenities they provide are amazing and they are a wonderful couple who respects your privacy but are there for anything you need. I recommend anyone to stay here and know they would want to return. Thank you John and Cathy for making our second summer with you a fantastic vacation!
Guest favorite
Condo in North Fork
4.84 out of 5 average rating, 106 reviews

Beautiful condo on Long Islands Northfolk

LauraRating, 5 stars1 month 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!
Guest favorite
Condo in North Fork
4.89 out of 5 average rating, 153 reviews

Beautiful Waterview Condo on the North Fork of LI

JeffreyRating, 5 stars4 weeks ago
Great retreat for a long weekend. Enough space for family of four. Easy access to everything in the Greenport area. Mia was very responsive, and the place was great. We would stay here again!
Superhost
Condo 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
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 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 favorite
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.
Condo in Hampton Bays
4.95 out of 5 average rating, 43 reviews

A Unique Piece of Paradise, Water Front pool

RoseRating, 5 stars4 weeks ago
This was my second time at Susan’s. The location on the bay with the beautiful views and sparkling clean pool will bring me back again. The house is always extremely clean and comfortable. Great location to walkable Rumba’s Restaurant. Susan is very reachable and a pleasure to rent from. I highly recommend it.

Home rentals with a private pool

Superhost
Home in East Hampton
4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

LarryRating, 5 stars48 months ago
House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.
Guest favorite
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 favorite
Home in East Hampton
4.98 out of 5 average rating, 131 reviews

Explore the Water & Woods at a Relaxing Retreat

DevonRating, 5 stars1 month ago
Jessica’s home was absolutely beautiful! We had an amazing, relaxing weekend and felt right at home :) Jessica is an amazing host - absolutely recommend staying here!!!!
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 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
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 vacation rentals with a pool in Shirley

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    840 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

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