
Family-friendly vacation rentals in Fairfield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Fairfield
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Fairfield family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Penthouse Minutes to Yale
Great location. Easy check in and out.

Dunes Beach House: Hot Tub and Steps to Beach
Great little spot. Nicely kept and a great spot for a get away.

Chic Beach House: Waterfront, Vineyards, Hot Tub
Our family rented for a weekend off season. Surroundings were beautiful. Home was clean and comfortable. Host was super friendly and very communicative. Any questions were answered within 5-10 minutes. Lots and lots of space for large groups. We had 6 adults, 2 children and a dog in our trip. Literally open the back door and you’re right on the beautiful beach!

The Mission House Sanctuary
The house was lovely and very clean and Piotr was an excellent host and even met us at check in to show us around. There are 4 bedrooms and each bedroom has its own bathroom which was very convenient for us. The kitchen was well stocked and It was very comfortable stay for my family of 7 adults and two babies and two dogs. One bedroom is on the main floor and two bedrooms are on the walkout lower level and one bedroom is on the upper floor. To get to the upper floor there is a steep winding staircase that wasn’t an issue for us, but I would not recommended it for small children or toddlers. The outdoor hot tub was a nice addition.

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC
My family was in town for a funeral, and we were able to book Victoria's home and save versus booking multiple hotel rooms. The location is minutes of I-95, so the home gave us a nice, central home base with a kitchen to get to everything and feed the kiddos between events. While we weren't looking for a beach trip - we were able to walk to the local beach and enjoy it with our young kids for a few hours over the weekend. The home was clean, comfortable, and worked perfectly for us. Communicating with Victoria was very easy, and check in/out was a piece of cake as there is a lock box on the house. If I need to bring the family back to the Stamford area, we'll definitely want to stay at Victoria's home again! Thanks!

Lake Life in beautiful updated Lake House
My parents and I really enjoyed our stay at Mark’s. His house was beautifully situated right on Lake Mahopac with plenty to do in town and in the surrounding area. Everything was as described and met all of our needs. Mark was extremely accommodating with our length of stay (~ 6 weeks) and allowing us to bring our animals (2 dachshunds, 1 cat). Check-in was easy and upon arrival we were greeted with a gift basket and a binder with all sorts of info (emergency, food, fun activities). The backyard was beautiful, completely fenced in, and super convenient for the pups. When we had questions, all we had to do was send off a quick text and Mark responded in a timely manner. I can’t recommend Mark’s place enough!

1ST FLR APT Your private resort, now FAMILY-ized!
It was great. Everything was the complete opposite of what I expected

Ensuite with private entrance
Had a wonderful stay and the host was extremely accommodating. This is the place to be!
Family- and pet-friendly home rentals

Quaint duplex + pvt yard. Walk to town & beach!
I had an amazing stay at this Airbnb! Henri was incredibly responsive and made sure all of my questions were answered promptly, which made the whole process seamless and stress-free. The home itself was spotless, well-maintained, and had everything we needed for a comfortable stay. It was spacious and thoughtfully stocked with all the essentials, from kitchen items to fresh linens. I felt right at home from the moment I arrived. Highly recommend this place if you're looking for a welcoming, comfortable, and well-equipped spot to stay!

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven
This is a lovely little beach cottage! We were very comfortable and had a great time! It was wonderful to have our dog with us! The location is beautiful and private, with access to a very special stretch of beach.

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
Johnny and Amy were amazing hosts. The instructions to park, enter and get in were very well written out before our arrival and check-in was seamless. And once we were there, the place was beautiful, cozy and exactly as described. Our kids loved running around outside in the grass and exploring the outdoor fire-pit. If you want peaceful mornings, laying in bed, watching the wind rustle the trees and listening to the birds sing their morning songs, this is a place for you.

The Farmhouse Estate Apartment
It was Very Great, calm, quiet. In our stay, the guests upstairs were very friendly, even during after hours. The vast land in the backyard was very enlightening , came across a couple of the friendly and nosy neighbors (The Deer😂 🦌). Overall it was very clean & i loved every minute of it.

Lakefront Country Oasis
Margie’s place is an amazing hidden gem. The inside is very clean and comfortable. The outside is an experience of its own. The lake will drop your blood pressure immediately. Gorgeous surroundings. The dogs are friendly and lovable. We will be back! 👍🏼

The Red Cottage Circa 1936
Jennifer's place was adorable, so many nice personal touches on the place. Exactly as described and the fish tank was a nice touch, very relaxing. Would highly recommend and will stay again next time im in town. Thank you for everything.

Cozy Cottage by the pond
Perfect stay in the coziest cottage! Rose & Jamie were amazing and super helpful and made us feel right at home.

Beachfront, Dog Friendly
Thank you for a wonderful stay and accommodating an extra night.
Family-friendly home rentals with a pool

Poolside apartment with private tennis court.
We had a wonderful stay at Todd's place! Todd greeted us warmly and was very responsive. The pool was fantastic and surrounded by beautiful nature, making it a serene spot to relax. We stayed in the pool apartment, which looked out at the pool and stunning backyard. It was well-equipped with a kitchen, pool towels, a TV, couches, and a dining table. Wendy, Todd's wife, welcomed us with cookies, and they provided milk, orange juice, eggs, yogurt, and fruits. There was also a grill available. We stayed for three nights and enjoyed the pool a lot. Despite being a shared pool, there was plenty of space and time for everyone. We also used the tennis court and played some basketball at the basketball rink there. Todd and Wendy made our stay very comfortable and enjoyable. We highly recommend their place!

Escape to a Restored New England Antique Milk Barn
When my plumbing went rogue and turned my floor into a squishy disaster zone, I needed a place to crash that wasn’t half underwater. Enter Sally’s place—a true oasis in my time of crisis. First off, this place is so nice that I briefly wondered if my house was even worth saving. It’s cozy, beautifully decorated, and so clean. The bedroom and bathroom are upstairs, making me feel like I was living the high life—literally. The bed? Like sleeping on a cloud. The view? So peaceful I considered writing poetry. Bottom line: If you need a place to stay, stop scrolling. Just book it. But be warned—you may never want to leave.

Private Hudson Valley Country Retreat
Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back

Pool House
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.

Garden Level Suite with Beautiful Pool
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Guesthouse & private pool, historic 24-acre estate
This place really is a gem. The bedroom and bathroom and spacious and have everything you need. The kitchen is small and can be challenging to work in, but the outdoor grill and dining space make up for that. We spent most of our time outside by the private pool relaxing. James and Margie were great hosts. They greeted us upon arrival and were so friendly and warm. They even brought fresh-bakes cookies. We had a great time!

1856 Trading House close to water
The space is adorable, and we loved the history of the rental and the community. The location was perfect for us—close to everything and secluded all at the same time. Also Jeff is an amazing host and made us feel welcome/at home. The next time we have to head to NY for a family visit we will definitely try to stay here again.

Newly-Renovated, Private, 4BR Cape w/Pool
Great home and host. Responsive to inquiries. Would recommend!
Quick stats about vacation rentals that are family-friendly in Fairfield
Total rentals
210 properties
Nightly prices starting at
$70 CAD before taxes and fees
Total number of reviews
4.2K reviews
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
130 properties have a dedicated workspace
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- Radio City Music Hall
- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Tenement Museum
- Riverside Park
- Comedy Cellar
- Yale University
- Apollo Theater
- Gilgo Beach
- St. Nicholas Park
- Yankee Stadium
- Citi Field
- Inwood Hill Park
- MetLife Stadium
- Bronx Zoo
- Astoria Park
- Rockefeller Center
- Dunewood
- United Nations Headquarters