
Holiday rentals with a pool in New Haven
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Top-rated rentals with a pool in New Haven
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House rentals with a pool

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

Private Oasis W/Stunning Vinyard and Pool Views
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!

The Perfect North Fork Escape
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.

Stylish Beach Getaway: pool & walking location
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.

Clinton Beach House & Cottage w/ Pool, Near Shore
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!

Hot Tub and pool Home away from home
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!

Restored Farmhouse + Pool in Heart of Wine Country
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.

Modern farmhouse w/ pool, beach, horses and winery
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

Cliffside Resort Poolside Condo A204
Very clean apartment! Easy check in/check out. Had a nice stay!

Charming Bayfront Condo
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.

Beautiful condo on Long Islands Northfolk
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!

Seaside Summer Escape: 2BR Waterfront Condo w/Pool
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.

Beautiful Waterview Condo on the North Fork of LI
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!

1856 Trading House close to water
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.

Beautiful 2 Bedroom 2 Bathroom Pool-Side Condo
Stay was great and the place was very clean

Waterfront Condo C-204 at The Cliffside Resort
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
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- Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Rye Beach
- Rye Playland Beach
- Cooper's Beach, Southampton
- Dunewood
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Thunder Ridge Ski Area
- Bethpage State Park
- Woodmont Beach
- Amagansett Beach
- Ocean Beach Park
- Quotonset Beach
- Rye Town Beach
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- Jennings Beach
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- Silver Sands Beach
- Sunken Meadow State Park
- Calf Pasture Beach