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Kid-friendly vacation rentals in Gloucester

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Gloucester kid-friendly rentals

Kid-friendly house rentals

Superhost
Home in Lakeside Marblehead
4.75 out of 5 average rating, 166 reviews

Walk to Everything Great about Marblehead!

RoryRating, 5 stars5 months ago
We loved our stay at this property. The house is much more historic and lived in, if you are after a pristine and modern stay, this might not be the place for you. But the house more than made up for it in character and cozy vibes, and it fit in perfectly in the charming historic neighborhood in Marblehead. The area has a lot of wonderful spots you can walk to, and the host provided historical information about the area and the house as well! We were so grateful for John’s proactive communication, we didn’t have any issues but I’m confident if we had he would have quickly resolved them! Overall my family had a wonderful weekend and we spent the drive home saying home much we’d love to make another trip in the summer to enjoy the ocean more!! Thanks John for a memorable weekend!
Top guest favorite
The exterior of the cottage is visible, featuring light gray siding and multiple windows with white trim. A vibrant display of pink flowers is situated in the foreground, providing a colorful contrast to the structure.
Home in Hampton Beach
4.96 out of 5 average rating, 272 reviews

2 Bedroom Beach Bungalow, Steps from the Beach!

ZaynaRating, 5 stars1 week ago
Out of the Airbnbs I’ve stayed at, this one has been my favorite! Sharon was very accommodating, left the best personal touches, and was so friendly and welcoming. Highly recommend this place for you & your loved ones
Guest favorite
A spacious backyard features a grassy area dotted with fallen leaves. In the background, a swing set is visible beside a wooden structure. The surrounding trees provide shade to the space, enhancing the outdoor environment for relaxation and play.
Home in Hyde Park
4.91 out of 5 average rating, 335 reviews

~*30min to Downtown*~ THE COSMOPOLITAN

NicholasRating, 5 stars4 days ago
Great place with great access to the city!
Guest favorite
A modern two-story house is surrounded by a spacious yard, featuring a well-maintained lawn and trimmed evergreen shrubs. A gravel driveway leads to the property, while trees provide a natural backdrop. The clear blue sky and gentle cloud formations add to the outdoor atmosphere.
Home in Reading
4.95 out of 5 average rating, 60 reviews

Charming Home in Reading with a Large Yard

JeffRating, 5 stars1 month ago
I recently stayed at Peter's place, and it was exactly as described in the posting. The pictures were accurate, and I was pleased to find the space clean and well-maintained upon arrival. The location is fantastic, as I grew up in the area. I truly couldn't have asked for a better experience. I wouldn’t hesitate to book again in the future. Highly recommend!
Superhost
A charming ranch-style home is showcased with a blue front door and classic window shutters. Two light-colored chairs are placed on the manicured lawn, surrounded by vibrant pink flowers. The entrance is framed by white railings and a well-maintained pathway.
Home in Seabrook Beach
4.76 out of 5 average rating, 82 reviews

Beach Bums' House - Perfect for Families & Friends

HollyRating, 5 stars5 months ago
This is an older ranch with a spacious kitchen and super comfortable beds. A beautiful beach is steps down the road. It is the first house off the highway, so you may hear traffic noise. There is a dehumidifier, which you will need to turn to the highest setting. The host is friendly and very responsive.
Superhost
A tranquil bedroom features a spacious bed with floral-patterned bedding. Two nightstands with matching lamps are positioned on either side. Natural light filters through sheer curtains, complementing the soft wall color and enhancing the serene ambiance of the room.
Home in Canton
4.83 out of 5 average rating, 168 reviews

3 bedroom impeccable private home, quiet street

KenRating, 5 stars2 weeks ago
Super nice house. Location is great and extremely quiet. Parking was no issue. Would stay again.
Top guest favorite
A backyard playset is anchored on a grassy area, featuring a blue slide, yellow swings, and pink swing seat. A wooden frame surrounds the playset, and a wooden fence encloses the area, offering privacy. Tall trees provide shade in the background.
Home in Billerica
4.98 out of 5 average rating, 209 reviews

Residential home ▪ Billerica ▪ quiet, clean & cozy

JanetRating, 5 stars1 week ago
We will definitely be visiting our family again and now are thrilled to know we have a wonderful Airbnb to stay at while visiting. It has all the amenities you might need and more, as well as entertainment, such as games, TV, and children’s outdoor and indoor activities. We will be back to visit before long. This will be our home away from home. Thank you Barry!
Top guest favorite
A spacious fenced backyard features a swing set and slide on rubber mulch, surrounded by greenery. The open lawn provides ample space for outdoor activities, while neighboring homes are visible beyond the fence, under a clear blue sky.
Home in Norwood
4.95 out of 5 average rating, 39 reviews

The Cozy Colonial - 4 BDRM house with parking

CalebRating, 5 stars2 weeks ago
What an absolutely lovely home that our family was thrilled to stay at! Very clean, quiet, and comfortable. Close to everything!! Certainly a 5 star stay!

Kid-friendly apartment rentals

Top guest favorite
A bright living area features a vibrant pink sofa with decorative pillows, complemented by a dark coffee table. Large windows allow natural light to fill the room, highlighting the hardwood floors. A simple chair and side lamp contribute to the inviting space.
Apartment in Cambridge
4.87 out of 5 average rating, 657 reviews

Lovely East Cambridge Apartment

HannahRating, 5 stars2 days ago
This place was cozy with everything you might need, even toys if you have small children. Jimmy was a very accommodating host; going above and beyond! We were so lucky to have this space for a very reasonable price. We all agreed the beds were comfy too, and it’s not easy to get approval from 4 different adults.
Superhost
A cozy living space features a gray sofa adorned with patterned cushions and a black coffee table. A vibrant yellow wall adds brightness to the room, while natural light filters through a window covered by sheer curtains. A spiral staircase leads to additional living areas.
Apartment in Charlestown
4.88 out of 5 average rating, 600 reviews

3 bed apt next to T- fast wifi-off street parking

ValerieRating, 5 stars1 day ago
We were extremely satisfied with Jurak’s place. We were thankful for timely responses and the flexibility to use entryway space for our luggage as we had many hours in the city without a place for our luggage. Three very comfortable beds with great linens. Lots of comfortable space for three friends to catch up and have access to the city. We would definitely come to this space again!
Guest favorite
A living area features exposed brick walls and wooden beams overhead. A large sectional sofa is positioned next to a low coffee table, with a television on a wooden media console across from it. Natural light filters in through windows, complemented by decorative wall art.
Apartment in East Boston
4.97 out of 5 average rating, 123 reviews

Quiet brownstone close to city

MeganRating, 5 stars2 weeks ago
Perfect location! Walked everywhere!!! Fabulous hosts! Loved our stay! We had the BEST time!
Top guest favorite
Apartment in Newburyport
4.97 out of 5 average rating, 195 reviews

City Loft | Group Getaway | King Downtown Location

AmandaRating, 5 stars1 week ago
The hosts were so friendly and accommodating. The condo was beautiful and cozy. Highly recommend.
Superhost
An open kitchen area features a wooden countertop with two tall chairs. Pendant lights hang above, illuminating the space. In the background, a dining table surrounded by four wooden chairs is visible, alongside kitchen appliances and a decorative plant.
Apartment in Malden
4.81 out of 5 average rating, 191 reviews

ENTIRE APARTMENT 3 BEDROOM CLOSE TO BOSTON

DouglasRating, 5 stars3 months ago
Great place, the house is wonderful, we like it a lot... the house was very clean, the kitchen is very well equipped, the street is very quiet to park the car... Tesfaye very helpful, friendly,.. I would definitely go back to rent this house ..
Guest favorite
Apartment in Jamaica Plain
4.85 out of 5 average rating, 193 reviews

1st Flr 2BR unit with parking + steps from train

KadenRating, 5 stars2 weeks ago
This was a great stay. Clean and exactly what it looks like in the photos. It was such a relief to find a place that could accommodate our family of 4, my need to telework while I was there, and also be clean and relaxing and close to family in Roxbury. Oh, and having off street parking is so incredibly valuable. Grateful we found this place & we'll definitely be back. There was a little technical difficulty that was no one's fault that delayed our ability to get in. George was responsive, apologetic, and addressed it immediately to our satisfaction. I'm delighted.
Guest favorite
Apartment in Cambridge
4.87 out of 5 average rating, 438 reviews

Cambridge Getaway @ Harvard & MIT

LindaRating, 5 stars1 month ago
This is an authentic Cambridge home that has been owned by the host's family for multiple generations. Kevin is accommodating, and he generously left some snacks and drinks in the full kitchen for us. Well-stocked kitchen was super convenient for eating breakfasts. Note: there are significant stairs to get into the unit. Once there it's quite spacious. And I love the operable bathroom window. :) Thanks for a lovely stay in a convenient, walkable neighborhood!
Guest favorite
The living room is furnished with a beige leather sofa and a dark brown armchair, complemented by warm wood flooring. A ceiling fan is mounted above, and natural light filters through two windows adorned with sheer curtains. A flat-screen TV and a coffee table are also visible.
Apartment in East Boston
4.97 out of 5 average rating, 200 reviews

Apartment w/Parking, minutes to airport / Downtown

KatieRating, 5 stars1 week ago
My family, including two young kids, found everything we needed here. We appreciated the kids' books and toys, snacks, etc. Joseph was very easy to communicate with and we felt right at home. Great to having on-site parking. It is a bit noisy because of the airplanes, but the kids had sound machines and were fine. Keep in mind that it's a bit of a drive if you want to do anything in Boston, although the nearby T is probably great for those with older kids. Overall a great stay and we would visit again!

Kid-friendly condo rentals

Guest favorite
A studio condo is showcased, featuring a queen size Murphy bed integrated into cabinetry. A large window provides natural light and views of the estuary. A comfortable seating area and stylish desk are visible along with a flat-screen TV mounted on the wall.
Condo in Seabrook Beach
4.84 out of 5 average rating, 107 reviews

Welcome to Marsh-Mellow! Seabrook Beach, NH

AmeliaRating, 5 stars8 months ago
My stay at the Marsh-Mellow, hosted by MaryJane, was phenomenal. From check-in to check-out, the process was simple as MaryJane had clear, detailed instructions on how to enter as well as great recommendations on what to do in the area. I have no hesitation when I recommend this space as your next getaway trip. You will not be disappointed!
Guest favorite
A well-lit hallway is visible, featuring beige walls and a light wood floor. To the left, an in-unit laundry area is equipped with a stacked washer and dryer. A door leads to the outside, and decorative wall art is displayed on the right.
Condo in Hampton Beach
5 out of 5 average rating, 10 reviews

Oceanfront 1 bed room condo with free parking

MelissaRating, 5 stars9 months ago
We had such a fantastic time, the only complaint is that it went by too quickly! Arun provided thorough instructions and was very responsive and friendly in communications. We were so appreciative that a special request was very kindly granted for a disabled family member. The place was just as pictured and had everything we needed. It was very clean and comfortable. The location could not be better, right in the heart of the Hampton boardwalk. Our favorite thing was sitting out on the balcony watching the waves roll in and enjoying observing all of the activity going on below us. We were lucky enough to be there on a night the fireworks went off and could not have had a better view right from that balcony! We would definitely recommend a stay here and hope to be able to return soon!
Superhost
A charming bedroom features a spacious bed with a colorful seashell-patterned duvet and decorative pillows. Light wood shiplap accent walls are complemented by soft peach paint. A ceiling fan and wall-mounted lamps provide illumination, while a small plant adds a touch of greenery.
Condo in Hampton Beach
4.84 out of 5 average rating, 128 reviews

Surfers' Paradise| 2 BD| Heart of HB| Sleeps 5

EmilyRating, 5 stars4 months ago
Very clean and spacious, the host was very helpful and always responded quickly. Very close to the beach which was beautiful. Stay was great!
Superhost
An open living area is visible, featuring a gray sofa, a patterned yellow armchair, and a dining table with six chairs. Large sliding glass doors provide access to a balcony, offering views of the outdoors. A kitchen counter and a coffee machine are also present.
Condo in Hampton
4.81 out of 5 average rating, 16 reviews

Serenity by the Sea

JamesRating, 5 stars7 months ago
Great place to stay with an awesome view of the beach right from the balcony. This is where every morning we would have our coffee to plan out our day and every evening sit back with a glass of wine and watch the moon rise over the ocean. The accommodations were good, the place was clean and had all the things to make our stay enjoyable. We would stay here again as well as recommend it to friends and family.
Top guest favorite
A bright game room is highlighted by a billiard table, foosball table, and a wall-mounted TV. A bar table with three stools is situated against a blue wall adorned with colorful artwork. Natural light filters through large windows covered by curtains.
Condo in Hampton Beach
4.89 out of 5 average rating, 158 reviews

Fun Game Room | Steps to Beach | 2 Level Lux Condo

MelissaRating, 5 stars1 week ago
What a fabulous week in Hampton Beach, even with the April weather! Really a great place to spread out and keep the teens AND adults entertained 😌 Sean was an amazing host and super responsive to questions and requests. Changed the water filter on the fridge, setup flowers for my daughter’s birthday! We will definitely be back here but next time in the summer!😁
Guest favorite
A stylish living area features a dark leather sofa positioned near a modern glass coffee table. A flat-screen television sits on a black media unit. Two windows provide natural light and a dining table is set for four, enhancing the open and functional layout.
Condo in Dracut
4.85 out of 5 average rating, 116 reviews

Cozy Entire Unit Condo close to UMASS Lowell

GiselleRating, 5 stars1 month ago
Amir’s condo was perfect for what I was looking for. It had all the kitchen essentials for my month-long stay, and the place was neat, tidy, and perfect for studying or working during the day with little to no noise from outside. Parking was right out front with easy in/out. Amir was proactive whenever I had any questions, and he resolved things right away. I’d recommend it to anyone looking for a nice, quiet place in the area.
Guest favorite
The image captures a view of the Atlantic Ocean, featuring gentle waves rolling towards the shore. A cloudy sky stretches above, while distant landforms can be seen along the horizon. Nearby buildings frame the scene, highlighting a coastal setting.
Condo in Hampton Beach
4.89 out of 5 average rating, 118 reviews

Oceanview Condo

TrishaRating, 5 stars7 months ago
We had a wonderful weekend getaway at John's place. It was a perfect location and very clean. John was great at communication and super nice. Thank you!!!
Guest favorite
The image captures a serene sunset over the ocean, with the sun rising above the horizon and reflecting warm orange hues across the calm water. A single figure can be seen on the beach, emphasizing the vastness of the tranquil scene.
Condo in Hampton Beach
4.94 out of 5 average rating, 108 reviews

Magical

CharlieRating, 5 stars7 months ago
Third year we’ve stayed there. Very well equipped unit. New sofa this year. The screened in porch overlooking the beach is a big attraction for us. You’re on the beach, so access isn’t an issue. Not one of the busier sections of the beach, but it’s a short walk to the areas with shops. An always accessible parking space, and an elevator to the upper floors is a plus.

Quick stats about vacation rentals that are kid-friendly in Gloucester

  • Total rentals

    100 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 before taxes and fees

  • Total number of reviews

    5.3K reviews

  • Family-friendly rentals

    90 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

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