Vacation rentals with a pool in New Haven County

Find and book unique homes with a pool on Airbnb

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Popular amenities for New Haven County rentals with a pool

House rentals with a pool

Guest favorite

Home in Fairfield

4.92 out of 5 average rating, 12 reviews

Once a Pond - time and stress slow down.

TameekaRating, 5 stars1 week ago
We just left yesterday and my family has already asked to go back! A beautiful, well-kept home with privacy but minutes from everything. The property looks exactly like the pictures. It’s cozy yet spacious and includes a lot of opportunities for relaxation. All of the survival touches did not go unnoticed. We appreciated every detail! Johanna was the ultimate host and was very responsive. We hope to go back when it’s a little warmer so that we can enjoy the pond and pool.
Superhost

Home in Milford

4.86 out of 5 average rating, 78 reviews

Spacious 4 bedroom, oasis with ocean views galore

LisaRating, 5 stars1 month ago
This house was absolutely perfect for my friends and I to gather together. The space was so comfortable and open which is perfect for a large group. We could all be doing something different but still close and comfortable. The location was perfect, easy parking between the driveway and street spots. The house had everything we needed, great bedroom setups. We didn’t have any kids with us but this would be a perfect place for facilities to come together. We want to come back in the summer and use the pool! Wouldn’t change a thing if we were to rent this home again. The host was super helpful and responsive and very friendly. 10/10 experience overall.
Guest favorite

Home in Middletown

4.95 out of 5 average rating, 40 reviews

Hot Tub and pool Home away from home

KristenRating, 5 stars3 weeks ago
Jan's house was a great stay with plenty of room for six adults. We loved the game room and outdoor hot tub. Instructions for the hot tub were clear and easy to follow. We'd definitely stay again!
Guest favorite

Home in Fairfield

5 out of 5 average rating, 16 reviews

4BR/2.5BA Refuge Near University, Downtown & Beach

CourtneyRating, 5 stars5 months ago
Our family visited Connecticut for a concert and we absolutely loved our weekend stay at Adam & Shelly’s! The place was clean and beautifully designed. Plus, our kiddos loved the pool! Shelly was responsive and accommodating. We couldn’t have asked for more. Would love to stay again!
Superhost

Home in Redding

4.89 out of 5 average rating, 19 reviews

5-bedroom modern farmhouse with heated gunite pool

JohnaRating, 5 stars3 months ago
The house and surrounding was beautiful. Brian and sooyun were very nice and very easy to communicate with. This was my first time getting an Airbnb, they made it very easy.
Superhost

Home in Roxbury

5 out of 5 average rating, 7 reviews

ShrinkMap to 5*Town Roxbury! Tophet 3BR PoshPadsCT

MorganRating, 5 stars23 months ago
Loved every minute! What a fantastic rental- far exceeded our expectations…jacuzzi/pool was incredible, I was so surprised how perfectly hot it was given how big it is! We had it at 104 and it was so fun to be in the pool in the winter. The house is so charming, so much character and the property is gorgeous. Great recommendations for restaurants in the book and lovely welcome treats (honey, maple syrup, wine) and gorgeous linens and bath products. Fun ping pong for the kids and lots of yard games! We will be back for sure!
Guest favorite

Home in Milford

5 out of 5 average rating, 8 reviews

Huge Family House w/Waterviews

LynnRating, 5 stars3 months ago
We had a wonderful stay! The house can accommodate large family gatherings - there were a lot of spaces for folks to spread out as well as gather. The kitchen is very well stocked. We would definitely rent again!
Superhost

Home in Fairfield

4.94 out of 5 average rating, 35 reviews

Newly-Renovated, Private, 4BR Cape w/Pool

PeterRating, 5 stars4 months ago
Great home and host. Responsive to inquiries. Would recommend!

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