Holiday rentals with a pool in New Haven

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for New Haven rentals with a pool

House rentals with a pool

Superhost
Home in Woodbury
4.95 out of 5 average rating, 19 reviews

2 homes in one (in-law design) w/salt water pool

ChristineRating, 5 stars8 months ago
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!
Top guest favourite
Home in North Fork
4.97 out of 5 average rating, 205 reviews

Private Oasis W/Stunning Vinyard and Pool Views

RebeccaRating, 5 stars3 weeks ago
We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!
Guest favourite
Home in North Fork
4.87 out of 5 average rating, 126 reviews

The Perfect North Fork Escape

RenataRating, 5 stars1 month ago
Laurie’s home was the perfect size for our girls weekend to celebrate the bride. The patio was extensive and comfortably fit all of us for a hibachi chef and dinner. It was a quick drive from the house to the wineries, which was fantastic.
Top guest favourite
Home in North Fork
5 out of 5 average rating, 13 reviews

Stylish Beach Getaway: pool & walking location

JenniferRating, 5 stars4 days ago
Maher’s home is so elegant and mid —such great taste. He was such a kind host and so very easy to communicate with. The pool was lovely and the garden and back so pretty. We had a brilliant time! Thank you.
Superhost
Home in Clinton
4.92 out of 5 average rating, 12 reviews

Clinton Beach House & Cottage w/ Pool, Near Shore

HannahRating, 5 stars5 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, 41 reviews

Hot Tub and pool Home away from home

KristenRating, 5 stars5 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 North Fork
5 out of 5 average rating, 37 reviews

Restored Farmhouse + Pool in Heart of Wine Country

KymberleeRating, 5 stars9 months ago
Absolutely loved our time on the farm. As someone who grew up out on the North Fork it was a return home with the most beautiful surroundings. Post Labor Day, the pool was still open (and warm)! The sun was shining during our bike rides to the incredibly close beach, and we had fresh veggies from the farm stand, right out front, every day. Such a treat, cannot wait to stay again and make some more great memories with family and friends.
Guest favourite
Home in North Fork
4.92 out of 5 average rating, 87 reviews

Modern farmhouse w/ pool, beach, horses and winery

SteveRating, 5 stars3 weeks ago
Travis and Morgan’s home is exactly like the photos. It’s spacious, well maintained and has most everything you’ll need for your stay. They are quick to respond to questions. Great central location for heading to downtown Riverhead for the aquarium or lunch, a quick 5 minute ride to Harbes and 10 to the north fork Waterdrinker location and 20-ish minutes to Greenport for a nice day trip. The kitchen is well equipped with plenty of cookware, dishes, utensils and a variety of spices. There’s room to spread out between the 3 bedrooms and the two living areas and the heated pool is a great bonus especially with kids in the mix. The yard is well kept and great for a well behaved pup to run around. Our only really issue with the home was the lack of dark blinds or curtains in the bedrooms. It got pretty bright once the sun rose each morning aka early mornings The en-suite bath is pretty tight for us tall folks. We had a great time and will definitely consider staying there again.

Apartment rentals with a pool

Apartment in North Fork
4.94 out of 5 average rating, 17 reviews

Cliffside Resort Poolside Condo A204

MichelleRating, 5 stars1 month ago
Very clean apartment! Easy check in/check out. Had a nice stay!
Apartment in Southampton

Charming Bayfront Condo

SaraRating, 5 stars8 months ago
Stop whatever you’re doing in the area and take 10 minutes to walk across the street to enjoy the sunset. I guarantee it’s addictive. Spent a post-Labor Day weekend with some friends and had an amazing time. The condo is centrally located between downtown Southampton, Bridgehampton and Sag Harbor and all that those areas have to offer. Several beaches, both bay-side and ocean-side, are also close by, but we mostly ended up lounging by the pool. The condo itself is spacious which is only further amplified by the amount of natural light reflecting off the bright interiors that let you know you’re near the beach. There are plenty of towels—both bath and beach—and there is ample beach equipment that you can use. The kitchen is fully stocked for cooking/dining at home, and there’s an outdoor patio equipped with a grill and dining furniture. Hostess could not have been nicer or more responsive, so I will definitely want to stay here again.
Guest favourite
Apartment in North Fork
4.84 out of 5 average rating, 106 reviews

Beautiful condo on Long Islands Northfolk

LauraRating, 5 stars1 month ago
We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!
Superhost
Apartment in North Fork
4.84 out of 5 average rating, 135 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

SeanRating, 5 stars2 weeks ago
We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.
Apartment in North Fork
4.89 out of 5 average rating, 152 reviews

Beautiful Waterview Condo on the North Fork of LI

SarahRating, 5 stars4 weeks ago
Mia’s place is excellent. Exactly what the listing describes and more — Mia is a great host and super attentive despite us being a last minute booking, she even helped us through a tough time late in the day when I thought my daughter’s stuffie had been picked up by the maid service. Above and beyond!
Guest favourite
Apartment in Mount Sinai
5 out of 5 average rating, 34 reviews

1856 Trading House close to water

JohnRating, 5 stars5 months ago
Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.
Apartment in North Fork
4.8 out of 5 average rating, 5 reviews

Beautiful 2 Bedroom 2 Bathroom Pool-Side Condo

JoshuaRating, 5 stars5 months ago
Stay was great and the place was very clean
Top guest favourite
Apartment in North Fork
4.88 out of 5 average rating, 98 reviews

Waterfront Condo C-204 at The Cliffside Resort

JennaRating, 5 stars5 days ago
Had an amazing stay in Greenport. The condo was exactly as listed, extremely clean and has a ton of amenities. Tom communicated from when the reservation was booked until the end, he was readily available, answered quickly and gave tons of informations. The location is ideal with the private beach and pool and a quick 5 minute drive into town. The condo offers a great little kitchen, a wonderful balcony with a water view and an unbeatable sunset and all the amenities you need for your stay. Pool towels are provided, plenty of bathroom towels, there’s a coffee machine, 3 tvs, a variety of dishware and there’s coin operated laundry in the basement. The staff that works the grounds and property are also super friendly. The town of Greenport and other surrounding towns are all close, you have endless options for vineyards in close vicinity and there’s tons of amazing restaurants within a 5-15 minute car ride. I highly recommend booking this property, I will definitely be rebooking! (If yo

Quick stats about holiday rentals with a pool in New Haven

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹1,714 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

  • Wifi availability

    20 properties include access to wifi

Destinations to explore