
Holiday rentals with a pool in New Haven
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in New Haven
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for New Haven rentals with a pool
House rentals with a pool
Guest favourite

Home in North Fork
4.98 out of 5 average rating, 43 reviewsPrivate pool/walk to beach; farms/vineyards abound
SuzanneRating, 5 stars6 months ago
Staying at Amy's place was perfect for my friends and I while we're out on the North Fork for a wedding. Amy was very responsive with any questions we had. We were all very comfortable in the main living area as well as our bedrooms. The house was conveniently located to the wedding venue and my friends were also very happy that it was located near some pickleball courts. Thank you Amy for a wonderful stay.
Superhost

Home in Clinton
4.91 out of 5 average rating, 11 reviewsClinton Beach House & Cottage w/ Pool, Near Shore
HannahRating, 5 stars3 months 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!
Guest favourite

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 favourite

Home in Fairfield
4.95 out of 5 average rating, 20 reviewsOld Post Road w/Pool and Cottage, walk to Beach
SophiaRating, 5 stars7 months ago
We had a great stay at Rose and Tom’s place and can’t wait to go back. From the start, Rose’s communication was super timely and clear. Tom met us at check in to show us the property and answer any questions, and remained available the rest of the weekend in case we needed anything. The house is extremely comfortable, clean, spacious. All the bedrooms were comfortable with plenty of towels and linens. The house has plenty locations to work from home as well. The location is a perfect 5 minute walk to town. We didn’t get to go to the beach, but it was very close and the house also had beach chairs/ towels in case we needed them. The pool house was an extra great and comfortable space to watch sports on the big TV with our group. The yard is perfectly manicured and the pool was heated, making our September stay even better. It was truly a great stay and wish we could have stayed longer.
Top Guest favourite

Home in Roxbury
5 out of 5 average rating, 16 reviewsBright Mid-Century Modern Retreat-90 min from NYC
SidRating, 5 stars2 months ago
My family and I had a wonderful weekend at the house. The house is beautiful and was extremely clean when we arrived. Luiz kindly left a sled for my kids to use in the yard. There is plenty of outdoor space and the yard has a good deal of privacy. There are two bedrooms and a den/office with a TV. The kitchen has everything we needed. Luiz was very easy to communicate with.
Guest favourite

Home in Redding
4.87 out of 5 average rating, 15 reviewsMeeker Hill House - Country Escape w/ Heated Pool
RoryRating, 5 stars6 months ago
Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend
Superhost

Home in Roxbury
5 out of 5 average rating, 7 reviewsShrinkMap to 5*Town Roxbury! Tophet 3BR PoshPadsCT
MorganRating, 5 stars26 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 favourite

Home in Woodmont
5 out of 5 average rating, 9 reviewsHuge Family House w/Waterviews
LynnRating, 5 stars6 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!
Quick stats about holiday rentals with a pool in New Haven
Total rentals
20 properties
Nightly prices starting at
$31 AUD before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
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- Beach
- Yale University
- Ocean Beach Park
- Dunewood
- Quotonset Beach
- Giants Neck Beach
- Cooper's Beach, Southampton
- Clinton Town Beach
- Woodmont Beach
- Shennecossett Beach
- Thunder Ridge Ski Area
- Rye Town Beach
- Marvin Beach
- Bethpage State Park
- Connetquot River State Park Preserve
- Shinnecock Hills Golf Club
- Weed Beach
- Oakland Beach
- Lloyd Beach
- Seaside Beach
- Walnut Public Beach
- Shoreham Beach
- Horton Lane Beach
- South Pine Creek Beach