Kid-friendly holiday rentals in Westport

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Westport family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Fairfield Beach
5 out of 5 average rating, 45 reviews

5 Minute Walk to Beach & Downtown Fairfield

FeliciaRating, 5 stars2 weeks ago
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!
Guest favourite
Home in West Norwalk
4.96 out of 5 average rating, 50 reviews

Modern Nature Retreat

MarkRating, 5 stars5 months ago
Beautiful house, great place for a relaxing weekend
Top guest favourite
Home in East Norwalk
4.95 out of 5 average rating, 20 reviews

Family friendly

DarrenRating, 5 stars3 days ago
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!
Guest favourite
Home in Rye
4.9 out of 5 average rating, 112 reviews

1956 House of the Year Award. Easy commute to NYC.

TinaRating, 5 stars6 days ago
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.
Superhost
Home in Rowayton
4.78 out of 5 average rating, 9 reviews

Coastal Comfort in Rowayton, CT

FawziaRating, 5 stars3 weeks ago
The house was just as described and just as the photos show. Spotlessly clean. Comfortable beds, linens and pillows. Pretty neighborhood, and peaceful.
Guest favourite
Home in Redding
4.88 out of 5 average rating, 16 reviews

Meeker Hill House - Country Escape w/ Heated Pool

RoryRating, 5 stars8 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
Guest favourite
Home in Fairfield
4.9 out of 5 average rating, 109 reviews

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking

JacksonRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Milford
4.99 out of 5 average rating, 110 reviews

The ARLO - Walk to Brewery & Restaurants

LaurieRating, 5 stars6 days ago
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

Top guest favourite
Flat in Fairfield
4.98 out of 5 average rating, 127 reviews

Sunny Fairfield Studio Apartment

MayaRating, 5 stars6 days ago
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!!
Top guest favourite
Flat in Ossining
4.96 out of 5 average rating, 438 reviews

Hudson River Peaceful Getaway, Explore from here

AlexisRating, 5 stars3 days ago
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!
Top guest favourite
Flat in Stamford
4.97 out of 5 average rating, 173 reviews

Standalone Cottage surrounded by woods

EireannRating, 5 stars6 days ago
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!
Guest favourite
Flat in Brookfield
4.92 out of 5 average rating, 280 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

BridgetRating, 5 stars2 weeks ago
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.
Guest favourite
Flat in Redding
4.94 out of 5 average rating, 484 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

JosephRating, 5 stars2 weeks ago
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.
Top guest favourite
Flat in Milford
4.98 out of 5 average rating, 104 reviews

The Pond Mill Retreat w/ 2 Bdrms & Pool

JudyRating, 5 stars1 week ago
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!
Superhost
Flat in Rocky Point
4.84 out of 5 average rating, 113 reviews

Cozy and Quiet space to Relax

KarenRating, 5 stars2 weeks ago
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!
Superhost
Flat in Newburgh
4.86 out of 5 average rating, 188 reviews

Special Nest w Private Entrance River View Porches

CynthiaRating, 5 stars2 weeks ago
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

Superhost
Apartment in Glenbrook
4.65 out of 5 average rating, 23 reviews

Clean 1 BD apt with Free Wi-Fi and parking

ConnorRating, 5 stars9 months ago
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.
Superhost
Apartment in Wooster Square
4.84 out of 5 average rating, 285 reviews

Stunning, Spacious, Spotless. Close to Yale.

TomRating, 5 stars2 weeks ago
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.
Guest favourite
Apartment in Middletown
4.94 out of 5 average rating, 154 reviews

Entire place to yourself Cromwell/Middletown Line

PamRating, 5 stars1 day ago
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.
Top guest favourite
Apartment in Highland Falls
4.96 out of 5 average rating, 107 reviews

Cozy West Point Hide Away and Cadet’s Get Away

GinaRating, 5 stars2 days ago
Great Airbnb! Great Host! Perfect for visiting West Point
Guest favourite
Apartment in Washington Heights
4.92 out of 5 average rating, 113 reviews

Private European Garden Apartment

FlorianRating, 5 stars3 weeks ago
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.
Guest favourite
Apartment in West New York
4.96 out of 5 average rating, 135 reviews

Gorgeous Brand New Condo Fully Loaded Mins to NYC

SachinRating, 5 stars1 week ago
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
Top guest favourite
Apartment in West Side
5 out of 5 average rating, 15 reviews

Comfortable, Beautiful Apartment-Close to Downtown

KarenRating, 5 stars6 days ago
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!
Guest favourite
Apartment in North Bergen
4.9 out of 5 average rating, 134 reviews

*M0DERN C0ND0 *MiNUTES TO NYC*

NatasiaRating, 5 stars1 week ago
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

Destinations to explore