
Vacation rentals with a pool in New Haven County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in New Haven County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for New Haven County rentals with a pool
House rentals with a pool
Guest favorite

Home in Fairfield
4.95 out of 5 average rating, 19 reviewsOnce 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 reviewsSpacious 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 favorite

Home in Middletown
4.95 out of 5 average rating, 40 reviewsHot 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 favorite

Home in Fairfield
5 out of 5 average rating, 16 reviews4BR/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 reviewsBeautiful 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 favorite

Home in Milford
5 out of 5 average rating, 9 reviewsHuge 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 reviewsNewly-Renovated, Private, 4BR Cape w/Pool
PeterRating, 5 stars6 months ago
Great home and host. Responsive to inquiries. Would recommend!
Guest favorite

Home in Wallingford
4.94 out of 5 average rating, 47 reviewsFamily 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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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Quotonset Beach
- Giants Neck Beach
- Clinton Town Beach
- Shennecossett Beach
- Thunder Ridge Ski Area
- Cooper's Beach, Southampton
- Woodmont Beach
- Marvin Beach
- Horton Lane Beach
- Mystic Seaport Museum
- South Pine Creek Beach
- Belmont Lake State Park
- Connetquot River State Park Preserve
- Lloyd Beach
- Steer's Beach
- Wildemere Beach
- Morningside Beach
- Anchor Beach
- Sasco Hill Beach
- Mohawk Mountain Ski Area
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