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Family-friendly vacation rentals in Brookline

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Brookline family-friendly rentals

Family-friendly home rentals with a hot tub

An open-concept kitchen and dining area features modern furnishings, including a long dining table surrounded by black chairs. Large windows offer views of greenery, allowing natural light to fill the space. A sleek kitchen island with bar stools complements the contemporary design.
Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars41 months ago
Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!
Superhost
The open layout showcases a living area with a comfortable sofa and decorative pillows. A granite counter separates the kitchen from the space, which features natural light from large windows adorned with light-filtering shades. A piece of framed art and a potted plant complete the ambiance.
Apartment in Roxbury
4.78 out of 5 average rating, 326 reviews

Modern, Spacious 1BR for 4 - Easy Marathon Access!

KatieRating, 5 stars1 month ago
Alex’s place was wonderful and a perfect location for someone who wants to travel Boston on foot. Very close to the T which made getting around really easy. Alex was also a very flexible, responsive, and kind host for our stay. Would definitely stay there again!
Superhost
A spacious backyard is shown, featuring a wooden playset with a slide and swings. Lush greenery surrounds the yard, with tall trees providing shade and privacy. The grass is well-maintained, creating a suitable area for outdoor activities.
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars7 months ago
The host communicated well and was very thoughtful. The bed wasn't very comfortable and the heating unit was a bit tricky to figure out, but overall, we had a great stay.
Guest favorite
A serene swimming pool is surrounded by lush greenery, with a rock feature and vibrant lounge chairs in various colors. A shaded seating area with an umbrella is visible, reflecting tranquility and inviting relaxation.
Apartment in Holliston
4.96 out of 5 average rating, 121 reviews

Lake Link

MichaelRating, 5 stars5 months ago
Our second time, weeklong stay! And we hope to do it again next year. Just simply meets our needs very well. It's a joy to stay here!

Family- and pet-friendly home rentals

Superhost
The exterior of a spacious antique house is shown, featuring a yellow facade with green shutters. A large deck is visible in front, complemented by a white picket fence. The house is set against a clear blue sky, adding a bright and welcoming appearance.
Home in Lakeside Marblehead
4.76 out of 5 average rating, 168 reviews

Walk to Everything Great about Marblehead!

BillyRating, 5 stars2 weeks ago
Great stay, house perfectly as advertised, super cute and great for a big group. John was easy to reach and was able to accommodate an early check-in and a late check-out. Would come back again!
Superhost
A well-equipped kitchen presents stainless steel appliances and an island with seating for four. Natural light floods the space through large windows, creating a bright and inviting atmosphere. The adjacent sunroom is visible through an open entryway, enhancing the home’s spacious feel.
Home in Wakefield
4.96 out of 5 average rating, 263 reviews

Welcoming 7-room house <15 miles to Boston & Salem

EmilyRating, 5 stars3 weeks ago
We loved staying here! Plenty of space for our family of 6, including one little one. It was exactly as pictured and well-stocked with spices in the kitchen and shampoo etc in the bathroom! Beds were super comfy and we loved how close it was to the lake, restaurants, and a playground. Would definitely stay here again!!
Superhost
An outdoor space is presented, featuring a wooden picnic table surrounded by a sprawling lawn. A slide is integrated into the landscape, complemented by vibrant greenery and a nearby garden area. Outdoor seating is also visible in the background, enhancing the communal atmosphere.
Condo in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars2 months ago
We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.
Superhost
A sitting area features a classic blue wall with two framed botanical prints above a marble fireplace. An orchid in a pink pot and a small potted plant add color. A comfortable armchair and a leather sofa complete the cozy layout, enhancing the inviting atmosphere.
Apartment in South End
4.96 out of 5 average rating, 378 reviews

Charming South End Duplex (Pets Ok)

KaitlynnRating, 5 stars1 week ago
Absolutely amazing place to stay! The host is sweet and responsive and it's in a great area :) lots to do just by walking around. My groups and I had a great time here and would come back again!
Superhost
A welcoming living room is equipped with two comfortable sofas, a wooden coffee table at the center, and a wall-mounted TV. Natural light enters through multiple windows, while a modern electric fireplace adds warmth to the space, enhanced by a vibrant area rug.
Townhouse in Allston
4.93 out of 5 average rating, 187 reviews

Sparkling Condo With Modern Amenities

AllisonRating, 5 stars9 months ago
Michelle was very responsive and great at communicating leading up to our stay. The house was easy to find, good neighborhood, perfectly clean and had everything we needed. Parking was included which was awesome. The T was easy to walk to so we could go downtown every day easily. The host recommendation for Lulu’s Allston was spot on, it was nearby and great. We felt right at home and had a wonderful stay and check out was also easy. Thank you Michelle for hosting a wonderful place!
Superhost
A cozy living room features a traditional fireplace with a decorative mirror above it. A wooden coffee table is placed in front of two patterned chairs. A white media console with a television is positioned against the wall, with light streaming through nearby windows.
Home in Beverly
4.95 out of 5 average rating, 154 reviews

Lovely 2 Bedroom Victorian 1.5 Blocks To Ocean!!!

DavidRating, 5 stars2 weeks ago
Great place and host! The ocean, great food, close to Endicott College, quiet and a beautiful area. Johanna was responded to questions and was proactive to leave lights on for us, knowing our flight would get us in late. There were some breakfast items waiting for us too! A nice welcoming touch to our stay!
Superhost
A sun-filled sunroom features classic wooden trim and large windows with blinds. A small desk is positioned beside the window, accompanied by a chair and decorative items. A cozy sofa sits nearby, enhancing the inviting setting.
Home in Medford
4.84 out of 5 average rating, 139 reviews

Sunny home minutes from Boston. Free parking.

EricRating, 5 stars2 weeks ago
Nice two-night family stay in this Medford neighborhood to coincide with Tufts graduation. Easy parking with convenient proximity to other commercial areas. Hosts were proactive in trying to address a temporary problem with the TV before we checked in - we had no plans to use the TV but appreciated the outreach and intention to address quickly. No problem during the stay but had the confidence that we could have reached out if there were any problems.
Superhost
The entrance features a spacious foyer with hardwood flooring. A console table with a lamp and decorative items is present, alongside a full-length mirror. Natural light enters through a window and the front door, enhancing the welcoming atmosphere of the space.
Home in Melrose
4.96 out of 5 average rating, 109 reviews

Upscale 5BR Family Home Near Boston

DaleRating, 5 stars1 week ago
The home was in a very nice and quiet area of town with groceries, gas and restaurants a short walk or drive away even in during busy hours of Boston traffic. The home was actually larger than expected with two full bathrooms, one on each floor. Everything was clean and ready for us with a well equipped kitchen and filtered water. There was a nice booth area to eat as well as counter seating and a dining room. We only had three in our party, but you could comfortably house a much larger family in the rental. We have a few more trips planned to Boston this year and will book this first if it is available, would like to stay again.

Family-friendly home rentals with a pool

An open-concept kitchen and dining area features modern furnishings, including a long dining table surrounded by black chairs. Large windows offer views of greenery, allowing natural light to fill the space. A sleek kitchen island with bar stools complements the contemporary design.
Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars41 months ago
Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!
Superhost
A spacious backyard is shown, featuring a wooden playset with a slide and swings. Lush greenery surrounds the yard, with tall trees providing shade and privacy. The grass is well-maintained, creating a suitable area for outdoor activities.
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars7 months ago
The host communicated well and was very thoughtful. The bed wasn't very comfortable and the heating unit was a bit tricky to figure out, but overall, we had a great stay.
Guest favorite
A spacious outdoor area features a crystal-clear pool surrounded by a paved deck. Several lounge chairs are positioned nearby for relaxation. The house in the background displays a welcoming design with a cozy porch. Lush greenery provides a serene backdrop to this inviting space.
Apartment in Winthrop
4.96 out of 5 average rating, 312 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

AndréRating, 5 stars5 days ago
The apartment was exceptionally clean, and exactly as shown in the photos. It had everything I needed for a comfortable stay — from a well-bathroom to a cozy bed and reliable Wi-Fi. The location was also a big plus: safe and quite. Katy, was a fantastic host — very responsive, friendly and proactive. They reached out to make sure everything was going well and answered any questions I had quickly and clearly. It really made the whole experience feel smooth and stress-free. Overall, I’d absolutely recommend this place to anyone looking for a comfortable and reliable stay. I’d be happy to return on my next trip!
Top guest favorite
A light yellow cottage is positioned adjacent to a spacious swimming pool, surrounded by lush greenery. The pool features a diving board and a decorative tile border. Two lounge chairs sit nearby, while steps lead up to the entrance of the cottage.
Guesthouse in West Roxbury
4.95 out of 5 average rating, 194 reviews

Country Cottage in the City

MariaRating, 5 stars6 days ago
What a perfect weekend in a private cottage by the pool. Although the weather did not cooperate for pool time, Mark & Susan’s cottage was a perfect place to have a central location outside of Boston. You would never know you were close to the city. Absolutely lovely! Their cottage was super clean and inviting and lacked nothing necessary for a long weekend away. They were very proactive in communicating with us about checking in and if we needed anything during our stay. Really terrific!
Guest favorite
A tranquil outdoor pool area is surrounded by lush greenery, featuring a swimming pool with a waterfall. Colorful chairs in pink and turquoise are positioned nearby, inviting relaxation. A hot tub is situated adjacent to the pool, contributing to the serene atmosphere.
Apartment in Holliston
4.96 out of 5 average rating, 121 reviews

Lake Link

MichaelRating, 5 stars5 months ago
Our second time, weeklong stay! And we hope to do it again next year. Just simply meets our needs very well. It's a joy to stay here!
Guest favorite
An aerial view captures the residential neighborhood near Nantasket Beach, featuring a well-maintained array of homes, some with lush greenery. The large backyard accommodates a heated pool, and the proximity to the beach is evident, with ocean waves visible in the distance.
Home in Hull
4.96 out of 5 average rating, 23 reviews

Spacious 3-BR Furnished Beach Home

BriannaRating, 5 stars11 months ago
We had a wonderful stay. Perfect place for families with children. So close to the beach with all the beach and home necessities you need while on vacation! Quaint town that was quiet but still has plenty of restaurants to visit. Overall, a great place!

Quick stats about vacation rentals that are family-friendly in Brookline

  • Total rentals

    410 properties

  • Nightly prices starting at

    $30 before taxes and fees

  • Total number of reviews

    14K reviews

  • Pet-friendly rentals

    130 properties allow pets

  • Rentals with a pool

    50 properties have a pool

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

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