
Kid-friendly holiday rentals in Westport
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Westport
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
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Popular amenities for Westport family-friendly rentals
Kid-friendly house rentals

5 Minute Walk to Beach & Downtown Fairfield
We had an amazing long weekend at Peter’s house. The house is great - close to the beach, and to an amazing playground if you have little kids like we do! He was so easy to work with, very responsive and flexible. Would definitely stay here again if we are ever back in this area!

Modern Nature Retreat
Beautiful house, great place for a relaxing weekend

Family friendly
Really enjoyed this stay. The property was very clean and the decor was superb. Would highly recommend this Airbnb for future reference. Communication was fast and sufficient!

1956 House of the Year Award. Easy commute to NYC.
A unique architectural home built 1955 that’s set on 2 plus acres surrounded by mature hardwoods. Set in a lovely neighborhood. Lots of interesting Art and Literature available to enjoy.I had wanted to stay on several visits but this location wasn’t available. I lucked out for 3 nights and so glad I had the opportunity to. I will definitely book again. Gloria was a responsive host. Instructions were clear and detailed. Lots of closet space in the 3 bedrooms and plenty space, multiple sitting areas. Thank you Gloria.

Coastal Comfort in Rowayton, CT
The house was just as described and just as the photos show. Spotlessly clean. Comfortable beds, linens and pillows. Pretty neighborhood, and peaceful.

Meeker Hill House - Country Escape w/ Heated Pool
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

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking
John and Crystal's place is in a safe and comfortable part of town. The space was well kept and well described. The bathroom and bedroom(s) were comfortable and definitely worth my time in Fairfield!

The ARLO - Walk to Brewery & Restaurants
The ARLO was super cute and very clean. It had ALL the amenities we needed. Outstanding communication with the hosts. Great welcome guide full of info. that answers all your questions. Looking forward to coming back 💕
Family-friendly apartment rentals

Sunny Fairfield Studio Apartment
Amazing place to stay if you are in the area! It’s at a great location, very peaceful neighborhood and lots to do. I will definitely be back if I am in the area again!!

Hudson River Peaceful Getaway, Explore from here
Dan & Jill’s home was beyond beautiful and comfy. It was very easy to find, private and felt safe. The inside of the home was more spacious than expected and extremely clean. The panoramic views from all windows was truly a treat. The hosts were very thoughtful and sweet. If you forgot to pack something, they most likely had it. Check in was smooth, stores/supermarket was a 3 min drive. 0 complaints and cannot wait to stay again!

Standalone Cottage surrounded by woods
This place was very cozy and clean. I enjoyed how peaceful and quiet the location was and wish we could've stayed longer to enjoy the backyard with our son. It was a perfect place to stay the night for our trip to a Yankees game!

Peaceful apartment on 3.5 acres w/ Artist studio.
We had to cut our stay short due to changes in travel plans, which was a pity because it was a really lovely and very comfortable place. I would strongly recommend it and hope to stay longer next time.

Huckleberry Quarters, the Cozy Redding Retreat.
The hosts were incredibly responsive and accommodating. The property and the space were gorgeous. The amenities were top notch and the kitchen ( which we took full advantage of ) had everything we needed. Would stay again in a heartbeat and would recommend it to anyone in need of a peaceful private getaway.

The Pond Mill Retreat w/ 2 Bdrms & Pool
Dawn and Bob’s place is one of the top Airbnb’s we have stayed in! Top notch in every way. It was spotless, comfortable and had everything we needed. And on top of that Dawn and Bob were the most friendly hosts we have met! I would recommend this Airbnb without reservation and will be back whenever we are back in CT!

Cozy and Quiet space to Relax
We really enjoyed staying at Patrick’s place. It was private, quiet & close to our family. He had thoughtfully supplied many kitchen supplies, dishes & everything we needed for our stay. Very organized & had many spaces to keep our things . Very comfortable apartment & smelled clean & fresh. Even had a small vacuum we could use to clean up tracked in leaves & dirt. We were there for a week & enjoyed having a stress free place to unwind!

Special Nest w Private Entrance River View Porches
The place was nice and roomy. Very accommodating. Sarah was fantastic at responding to getting us a coffee pot of which the place did not have one. That was so much appreciated. I hope her future guess will appreciate that also.
Family-friendly apartment rentals

Clean 1 BD apt with Free Wi-Fi and parking
My friend and I stayed for a short trip at Maria's location and it was exactly what we needed, a place to stay for our trip that was well kept, had amenities, and fresh linen available. Parking spot was small, but is to be expected in an attached parking garage.

Stunning, Spacious, Spotless. Close to Yale.
Over $500 a night was very high, much higher than west Coast pricing for two bedrooms near a major university. Convenient to Yale but know that poverty has always been evident a few feet from Yale borders and much of the foot traffic consists of the homeless. Also some noise at night from passing traffic. On the plus side there’s an excellent Italian bakery/gelato cafe across the street run by a husband wife team that makes everything they serve.

Entire place to yourself Cromwell/Middletown Line
Will definitely be repeat customers when we come back to CT to see friends and family. The place is exactly as described, spotless and was a home away from home. Elizabeth answered any questions quickly. Thank you for making our first experience with Air Bnb a positive one.

Cozy West Point Hide Away and Cadet’s Get Away
Great Airbnb! Great Host! Perfect for visiting West Point

Private European Garden Apartment
Beautiful place, functional. clear and efficiently laid out. Easy to access with Subway and buses, many shop and restaurants within a short walking distance. Ann was very responsive and helpful before, and during the stay. Only challenge was to find a nearby parking stop when arriving late at night but this is to be expected in NYC.

Gorgeous Brand New Condo Fully Loaded Mins to NYC
Olga is an excellent and friendly host, I have experienced so far. The apartment was awesome, precious and unexpected amenities. Host was highly responsive and reachable

Comfortable, Beautiful Apartment-Close to Downtown
I am new to the Stamford / Greenwich area and needed a place to stay while I looked for a permanent residence. I stayed at Juan's place for about 3.5 months. It was very convenient to Greenwich (where I work) and to downtown Stamford (restaurants and shops) and the Stamford train station, which has great express trains to NYC. It is also very close to a grocery store and several gyms (I chose Orange Theory, only a few blocks away). I chose Juan's place for the location and king size bed. The bed was very comfortable, the towels were great and the overall unit worked really well for myself and my husband - it has wifi and we connected to our Netflix & other apps thru the smart TV. It fits two people comfortably and has a pull out sofa for guests (my college-age children visited a few times). The kitchen has what you need, including a dishwasher. There is one permanent parking space available and several guest spots. Juan was very responsive and a great host. Highly recommend!

*M0DERN C0ND0 *MiNUTES TO NYC*
We had a very comfortable and enjoyable stay. Your place was clean, well-equipped, and felt like a home away from home. We really appreciated your hospitality and the smooth communication throughout.
Quick stats about holiday rentals that are kid-friendly in Westport
Total rentals
40 properties
Nightly prices starting at
₹7,707 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Gilgo Beach
- United Nations Headquarters
- Rye Playland Beach
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Bronx Zoo
- Central Park Zoo
- Radio City Music Hall
- The Metropolitan Museum of Art