Holiday 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 favourite

Home in Fairfield

4.92 out of 5 average rating, 13 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 Clinton

4.91 out of 5 average rating, 11 reviews

Clinton Beach House & Cottage w/ Pool, Near Shore

HannahRating, 5 stars3 weeks ago
We had a group of 8 adults and 7 kids (5 and under) and the space was great for a large group! There was plenty of room for the kids to run around downstairs and the large yard was fantastic. We were there in the winter so couldn’t take advantage of the pool but we did make a trip to the local beach (5 min drive) and use the fire pit. I definitely recommend Gregory’s place for both larger groups and families! We would love to return!
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 favourite

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 favourite

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.
Guest favourite

Home in Roxbury

4.89 out of 5 average rating, 19 reviews

Zoom Map 5* Town Roxbury! "SentryHill" PoshPadsCT

BrittRating, 5 stars2 months ago
Beautiful property and well equipped home in a quiet neighborhood. Great for a relaxing getaway with friends or family. The yard has additional amenities for kids to enjoy outside time. The house has great WiFi but would be helpful to know that cell service is limited.
Guest favourite

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!

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