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
4.95 out of 5 average rating, 19 reviews

Once a Pond - time and stress slow down.

KerrinRating, 5 stars3 weeks ago
We stayed here for a weekend while visiting our daughter at Fairfield University. The location was perfect! The house was beautiful- it reminded me of a modernized cottage. Everything was spotless - made you feel instantly at home! We will absolutely be back! We tried for upcoming parents weekend in October 2025 and she's already sold out!! Definitely book - you won't be disappointed!
Superhost
Home in Milford
4.84 out of 5 average rating, 82 reviews

Spacious 4 bedroom, oasis with ocean views galore

BrianRating, 5 stars1 week ago
Classic charming beach house, updated with all the amenities. great views of the water and unbeatable sunrises. 2nd floor deck was very enjoyable for morning coffee made at the coffee bar owner was very responsive when a smoke detector needed a battery as extras were on site and she responded very quickly to a message for help. Family room was the hub of our activity with a generous dining table and views from the open kitchen. Heat/AC kept us comfortable on the chilly mornings. House is on quiet street a few houses from the Restaurants start a few blocks away and a short drive.
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 months 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 stars7 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!
Home in West Haven
4.81 out of 5 average rating, 184 reviews

Beautiful Modern house By the Bay w out door Spa

JeanRating, 5 stars2 weeks ago
Sim was great and very responsive. The house was missing a few utensils when we got there. I texted Sim and a few hours later, they arrived at our doorstep! When I didn't know how to start the fireplace, she immediately sent me a video showing me how. Worked perfectly. This was a big birthday for me and a gathering of all my close friends. The house was perfect for this. A big shout out to Sim!
Guest favourite
Home in Milford
5 out of 5 average rating, 9 reviews

Huge Family House w/Waterviews

LynnRating, 5 stars5 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 stars6 months ago
Great home and host. Responsive to inquiries. Would recommend!
Guest favourite
Home in Wallingford
4.94 out of 5 average rating, 47 reviews

Family Oasis 4bd/2ba Private Home & Yard

AnitaRating, 5 stars1 month ago
Jill’s place was perfect for our family of 6 with 2 kids (ages: 6&2). There was plenty of space and beds and bedrooms. Jill had very useful and clear instructions around the house. There were also toys for the kids to play with so that was a very fun surprise. It was well heated while we were there and there were extra comfy blankets anyways. Jill gave many good restaurant suggestions! Would recommend!

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