
Kid-friendly vacation rentals in Gloucester
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Top-rated kid-friendly rentals in Gloucester
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Popular amenities for Gloucester kid-friendly rentals
Kid-friendly house rentals

Walk to Everything Great about Marblehead!
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!

2 Bedroom Beach Bungalow, Steps from the Beach!
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

~*30min to Downtown*~ THE COSMOPOLITAN
Great place with great access to the city!

Charming Home in Reading with a Large Yard
We thoroughly enjoyed our stay. The location was wonderful and the hosts were extremely easy to work with

Beach Bums' House - Perfect for Families & Friends
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.

3 bedroom impeccable private home, quiet street
Super nice house. Location is great and extremely quiet. Parking was no issue. Would stay again.

Residential home ▪ Billerica ▪ quiet, clean & cozy
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!

The Cozy Colonial - 4 BDRM house with parking
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

Lovely East Cambridge Apartment
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.

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

Quiet brownstone close to city
Perfect location! Walked everywhere!!! Fabulous hosts! Loved our stay! We had the BEST time!

City Loft | Group Getaway | King Downtown Location
The hosts were so friendly and accommodating. The condo was beautiful and cozy. Highly recommend.

ENTIRE APARTMENT 3 BEDROOM CLOSE TO BOSTON
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 ..

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

Cambridge Getaway @ Harvard & MIT
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!

Apartment w/Parking, minutes to airport / Downtown
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

Welcome to Marsh-Mellow! Seabrook Beach, NH
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!

Oceanfront 1 bed room condo with free parking
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!

Surfers' Paradise| 2 BD| Heart of HB| Sleeps 5
Very clean and spacious, the host was very helpful and always responded quickly. Very close to the beach which was beautiful. Stay was great!

Serenity by the Sea
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.

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

Cozy Entire Unit Condo close to UMASS Lowell
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.

Oceanview Condo
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!!!

Magical
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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- Hampton Beach
- Wells Beach
- Boston Common
- TD Garden
- Fenway Park
- Harvard University
- North Hampton Beach
- Ogunquit Playhouse
- Long Beach
- New England Aquarium
- Faneuil Hall Marketplace
- Long Sands Beach
- Freedom Trail
- Prudential Center
- Symphony Hall
- Boston Public Library
- Crane Beach
- Rye North Beach
- Aaronap Cellars
- John Hancock Tower
- Boston Children's Museum
- Quincy Market
- Pavilion Beach
- Wentworth by the Sea Country Club