Vacation rentals with a pool in Westchester County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Westchester County rentals with a pool

House rentals with a pool

Superhost

Home in Port Chester

5 out of 5 average rating, 10 reviews

Labrador Manor: Westchester County Home with Pool

DianeRating, 5 stars4 months ago
The Labrador Manor was impeccable. Air conditioned and beautifully decorated The pool was magnificent with lots of sun beds and seating. Completely enclosed for privacy. 10 out of 10👏👏
Guest favorite

Home in Wilton

5 out of 5 average rating, 19 reviews

Historic 3 Acre Estate | Pool+HotTub | Firepit+BBQ

ElizabethRating, 5 stars1 month ago
We were blown away with the history and charm of this home. With all updated amenities, the owners were able to keep the history flowing through every room. Just 7 minutes from downtown Ridgefield it was the perfect location to stay with extended family and still be part of all the fun Ridgefield has to offer.
Guest favorite

Home in Stamford

4.98 out of 5 average rating, 51 reviews

Gameroom, backyard + pool! 7m to train + downtown

TammieRating, 5 stars2 months ago
Diego and Ya went above and beyond during our stay. They were very attentive and responsive and helped make our stay comfortable. We highly recommend their property. They are wonderful hosts!
Superhost

Home in Yonkers

5 out of 5 average rating, 7 reviews

Classic Luxury Home in Prime Location!

ChikkuRating, 5 stars2 months ago
Great house in a quite neighborhood. House is beautiful and had plenty of space for our group. Backyard is really nice with sitting areas, hot tub and play area for kids. Has a great mix for adults and kids. The 3 bedroom and 3 full bath upstairs was really nice. The extra bedroom and full bath downstairs was very useful. Kitchen has some basic pots and pans for any small cooking needs. Overall great place and would recommend for others!

Home in Katonah

4.8 out of 5 average rating, 5 reviews

Luxury 4 bedroom Modern Barn with Pool

ThomasRating, 5 stars4 months ago
Our stay at this unique home was fantastic! The 5 acres of beautiful land provided a perfect backdrop for relaxation and fun. The kids especially loved the pool and spent hours playing in it. The downstairs play area with a ping pong table was a big hit too. The open layout of the house was perfect for family time, and the large deck was ideal for outdoor meals and cozy evenings. The bedrooms were comfortable, and the extra sleeping spaces were a great addition. A highlight of our stay was the chickens. The kids had a blast collecting fresh eggs every morning. Overall, this home exceeded our expectations and provided an great experience.

Home in Pound Ridge

5 out of 5 average rating, 4 reviews

Secluded Modern Getaway-Seasonal heated pool

LucindaRating, 5 stars3 months ago
I can’t say enough good things about our stay in Pound Ridge! The house is truly stunning — like something out of the Hollywood Hills set in nature, and so private. It was a thrill to pull up in the driveway alone. The pool was spotless and warm; the floor to ceiling window views were divine to wake up to every morning. All of the furniture and kitchen/bathroom items were so thoughtfully chosen and well-appointed—I ended up purchasing replicas for my own home! We hadn’t expected the house to be as convenient as it was…a very quick drive to town, and less than 20 minutes to New Canaan where there was plenty to do in town. Great camps and activities for kids/families. All of the food was shockingly good. My family feels quite fortunate to have found such a treasure online for our summer stay. Sushma could not be more responsive, friendly, and went above and beyond. Her lovely housekeeper takes such pride in keeping her guests comfortable and right at home. Highly recommend!
Guest favorite

Home in Carmel Hamlet

4.93 out of 5 average rating, 71 reviews

Country getaway with hot tub on 9 acres

JoelRating, 5 stars4 months ago
Calum’s home was super clean and comfortable. The host was responsive and helpful. The AC worked great and the house temperature was comfortable. I paid to have the pool heated and it was a nice temperature. It was an overall very good experience and I recommend Calum’s place.

Home in Waccabuc

5 out of 5 average rating, 3 reviews

Lakefront home with multiple bedrooms, indoor and outdoor entertaining areas.

DanielRating, 5 stars16 months ago
We really enjoyed our stay at Beth's! It was so peaceful and wonderful to be right on the lake but also to have a pool! Our family is nearby, so we will def book again when we visit!

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