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Kid-friendly holiday rentals in Westport

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Westport kid-friendly rentals

Child-friendly house rentals

Guest favourite
Home in 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 Norwalk
4.95 out of 5 average rating, 20 reviews

Family friendly

DarrenRating, 5 stars5 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 stars1 week 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.
Superhost
Home in Fairfield
4.81 out of 5 average rating, 126 reviews

Southport Shoreline Charm: Elegant Coastal Escape

KaraRating, 5 stars1 month ago
Perfect for SHU graduation. 10 mins from Amphitheatre and close enough to the college. Drew was very responsive answered my inquiries within minutes. House was spacious, comfortable and had everything we needed for a long weekend. As others have noted it is very close to the highway. The first night we notice the noise when going to bed but soon it was white noise and the remaining nights we did not even notice it. Best part of the long weekend was our dog got to join us.
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
4.98 out of 5 average rating, 50 reviews

Luxury Beach House | 3 Bd-King | Chef Kitchen |4 TV

ChristinaRating, 5 stars1 week ago
We had the best time at the beach house! We have two toddlers and the location of the house was perfect! Easy walk to the beach. They played in low, medium and high tide and loved them all equally. Sunsets from the deck are breathtaking. Morning walks on the quiet block and along the beach were so peaceful. The surrounding town is adorable with some great restaurants. Kids had a blast at dockside brewery. House was super clean, host always responsive and neighbors were kind. We can’t wait to come back!

Kid-Friendly apartment rentals

Top Guest favourite
Apartment in Milford
4.95 out of 5 average rating, 161 reviews

The Boathouse, private downtown Harborside suite

ZoeRating, 5 stars5 days ago
⭐️⭐️⭐️⭐️⭐️ Clean, Comfortable, and Thoughtfully Prepared! We had a great stay! The place was spotless, quiet, and exactly what we needed for a few nights of good sleep and hot showers. It was clear that the host put thought into making guests feel welcome—there was a mini chocolate bar and a bottle of water waiting for each of us when we arrived, which was such a kind touch after a long day of travel. Check-in was smooth, the bed was comfortable, and everything worked perfectly. While we didn’t spend much time there beyond resting, it was the perfect place to recharge. Highly recommend for anyone looking for a clean, convenient, and cozy spot!
Top Guest favourite
Apartment in Fairfield
4.98 out of 5 average rating, 128 reviews

Sunny Fairfield Studio Apartment

MayaRating, 5 stars1 week 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
Apartment in Stamford
4.97 out of 5 average rating, 174 reviews

Standalone Cottage surrounded by woods

EireannRating, 5 stars1 week 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
Apartment in Port Jefferson Station
4.9 out of 5 average rating, 116 reviews

The Elite Enclave

SarmadRating, 5 stars1 week ago
Great place , nice people , very commucative, place has everything you need , clean , and felt home , definitely will come back again for great experience
Guest favourite
Apartment in Brookfield
4.92 out of 5 average rating, 281 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Jose CarlosRating, 5 stars2 weeks ago
The place was really nice and the host was great! Don’t get discouraged if the power goes out during your stay cause apparently that’ll happen 2-4 times a year according to the host. Other than that I highly recommend
Guest favourite
Apartment 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
Apartment 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
Apartment 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!

Child-Friendly Holiday Condos

Superhost
Condo in Upper West Side
4.93 out of 5 average rating, 122 reviews

Best of the west! Sunny,quiet&huge! Ideal location

SergiiRating, 5 stars2 months ago
Location Location Location! Very hard to find a neat place to stay on UWS. This apartment has great restaurant selection right at the door step. Either for a cozy dinner or kids crazy morning routine. Keep in mind this is NYC so not elevator access if you need but it was ok for us even with stroller. Overall recommend this place if you budget allows.
Superhost
Condo in Downtown New Haven
4.84 out of 5 average rating, 285 reviews

Stunning, Spacious, Spotless. Close to Yale.

TomRating, 5 stars3 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.
Superhost
Condo in Middletown
4.94 out of 5 average rating, 154 reviews

Entire place to yourself Cromwell/Middletown Line

PamRating, 5 stars3 days 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.
Superhost
Condo in Highland Falls
4.96 out of 5 average rating, 107 reviews

Cozy West Point Hide Away and Cadet’s Get Away

GinaRating, 5 stars4 days ago
Great Airbnb! Great Host! Perfect for visiting West Point
Superhost
Condo in Downtown Stamford
4.98 out of 5 average rating, 42 reviews

Downtown Living w/ parking, W/D & Wi-Fi+!

RajkumarRating, 5 stars1 week ago
Very nice location, quiet, yet central . House was well stocked and Aaron was prompt with communication. I had to modify my itinerary and Aaron was very accommodating.
Superhost
Condo 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
Superhost
Condo in Stamford
5 out of 5 average rating, 15 reviews

Comfortable, Beautiful Apartment-Close to Downtown

KarenRating, 5 stars1 week 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!
Superhost
Condo 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

    $150 NZD 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