Family-friendly vacation rentals in Westwood

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Westwood family-friendly rentals

Family-friendly home rentals with a hot tub

A private backyard features a heated pool surrounded by a spacious deck. The contemporary two-story home, with large glass windows and doors, provides views of the lush greenery. Lounge chairs and umbrellas are arranged for outdoor relaxation.
Home in New Seabury
5 out of 5 average rating, 26 reviews

New Seabury pool/hot tub near beach,Popponesett

NicoleRating, 5 stars10 months ago
We stayed here for a bachelorette party and the house exceeded our expectations. Sherri was responsive and quick to answer all of our questions before and during the stay.
Guest favorite
An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.
Home in Hopkinton
4.95 out of 5 average rating, 153 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars2 days ago
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.
A bright bathroom features a glass shower with colorful accessories visible. Soft towels are neatly arranged on a rack, and a large window provides natural light. An art piece with coastal imagery is displayed on the wall, enhancing the serene atmosphere.
Cabin in Falmouth
4.66 out of 5 average rating, 581 reviews

Waterside Guest House

KerryRating, 5 stars1 week ago
The view out the window to the ocean was spectacular and the accommodations were very pet friendly, my two dogs were very happy hanging out on the two couches in the living room. Perfect place to serve as a home base for exploring the quaint restaurants and shops in downtown Falmouth. Full kitchen if you want to cook, and plenty of furniture to have guests for dinner with a good size kitchen table. Ron, was very available and friendly, and I will definately go back!
Superhost
Townhouse in Mashpee
5 out of 5 average rating, 3 reviews

4th July week! Cape Cod Townhome

DmitryRating, 5 stars82 months ago
The place is great if you don't mind having to drive to a beach or to town. It's spacious and clean. And Ruth is a great host. She was very responsive.
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 stars6 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 contemporary kitchen features white cabinetry and a spacious island with seating. Modern appliances, including an oven and dishwasher, are visible. Natural light enters through a window, illuminating the marble countertops and the stainless steel range hood, enhancing the kitchen's functionality.
Home in East Falmouth
4.9 out of 5 average rating, 60 reviews

Peaceful waterfront home with dock/ hot tub

ConorRating, 5 stars8 months ago
We stayed at this home with a group of five people and the home fit everyone great. The view from the home of the marsh is beautiful and we spent Saturday hanging out on the dock. It is really peaceful and we had an amazing time. Michele was a pleasure to work with and was very accommodating with being flexible for check in and check out times. Thank you again!
Superhost
A charming two-story home is framed by lush greenery, featuring a sloped roof with solar panels. A driveway leads up to a spacious garage, while well-maintained gardens and neatly trimmed hedges enhance the inviting exterior.
Home in Plymouth
4.87 out of 5 average rating, 79 reviews

Amazing ocean front 3 bedroom

CrystalRating, 5 stars6 months ago
We had a wonderful stay! The house was great! Views were awesome from the top balcony! We wished the bushes and shrubs had been trimmed a little to have a better view from the main level but it was still a nice view from the one area there. House was quite roomy and had everything we needed in the kitchen. There are not tvs in the two spare rooms which would have been good after dinner for our teenagers while winding down after family time. The host is wonderful and communicated great. Overall we had a great family vacation and a good time. The house is nice. Would recommend!

Family- and pet-friendly home rentals

Top guest favorite
A comfortable living room is highlighted by a large flat-screen TV mounted on the wall. Two recliner sofas are positioned around a wooden coffee table, while warm wood floors and ample natural light from multiple windows enhance the inviting atmosphere.
Home in Wakefield
4.96 out of 5 average rating, 260 reviews

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

TyroneRating, 5 stars1 week ago
Karen was absolutely incredible. She was very responsive, respectful, and accommodating. We very much enjoyed our stay as my team and I were there on business. She was able to take care of us even on short notice. I really couldn’t be happier with her communication, the quality of their home, and the entire experience. Thank you so much Karen for inviting us into your home. This was truly a 12/10 experience. 😃😃
Top guest favorite
A wooden cabin with a sloped roof is surrounded by a snow-covered landscape. The porch is visible, along with two friendly dogs playing in the snow. Tall trees, dusted with snow, create a serene, wintry atmosphere.
Cabin in Rockport
4.97 out of 5 average rating, 447 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

AnaisRating, 5 stars1 week ago
Our stay at Dogtown Cabin was absolutely wonderful! Julie was consistently available for any questions or concerns and she was kind and welcoming and made sure we had everything we needed. The cabin itself was cozy yet spacious. Plus it was equipped with everything we needed to help make our stay comfortable. They had some great trails on the property and my family had a great time exploring them. The beautiful property is serene and private but close enough to a lot of tourists destinations. And let’s not forget the animals! My son had a great time meeting the horses and chickens. But I will say hands down the best part of our stay were our adorable furry hosts, Darwin and Azore! They greeted us every morning! Hanging out with them made our stay even more special! We honestly can’t wait to come back.
Guest favorite
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 stars1 month 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.
Guest favorite
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, 374 reviews

Charming South End Duplex (Pets Ok)

HelenRating, 5 stars2 days ago
We just a wonderful few days in Boston for the marathon. Maude was the perfect host… we really appreciated the flexibility with check-in and check-out and were so grateful for the provisions left for us, particularly as we arrived late! The location is perfect, it meant that we could explore everywhere in the City on foot. The neighbourhood is particularly great for restaurants and when the sun came out and the temperature rose, the vibe was fabulous. As a previous review mentioned, if you’re looking for a pristine, freshly painted apartment then it’s not for you, but if you like ‘quirky’ and a house with bags of character, (I especially loved the art), then I’d highly recommend.
Guest favorite
A bright living room features spacious seating with two comfortable couches, providing ample space for relaxation. Natural light enters through large windows, highlighting the light-colored walls and wooden flooring. A flat-screen TV is mounted on a simple console, while a decorative plant and framed artwork enrich the space.
Townhouse in Allston
4.93 out of 5 average rating, 186 reviews

Sparkling Condo With Modern Amenities

AllisonRating, 5 stars8 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 spacious bedroom and living area is depicted, featuring a wooden bed with a white comforter, a brown leather sectional sofa, and two small side tables. Natural light filters through large windows, while a door leads to the outside. Neutral-colored walls and a patterned rug enhance the inviting ambiance.
Home in Sandwich
4.93 out of 5 average rating, 211 reviews

Cottage in the heart of the village

JeffRating, 5 stars8 months ago
Great location away from all the hustle and bustle of the Cape, but close enough to see it all. Highly recommend staying here, very relaxing, quiet, and walkable to a few restaurants and bars to unwind after a long day of exploring the Cape. Cute and cozy! Do yourself a favor and get up for Sunrise at Sandwich Boardwalk during your stay.
Guest favorite
The exterior of a Victorian home is showcased, featuring colorful trim and decorative elements. A set of stairs leads to a front door adorned with a wreath. Lush greenery and potted plants are visible, enhancing the inviting entrance.
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
A serene pond-front view captures a charming green house surrounded by lush trees and a well-maintained yard. Water's smooth surface reflects the structure, enhancing the tranquil atmosphere. Nearby foliage hints at seasonal changes, adding to the picturesque outdoor setting.
Home in Plymouth
4.96 out of 5 average rating, 157 reviews

1 of a Kind Pond-Front Home, Minutes from Downtown

WadeRating, 5 stars4 months ago
We loved staying at this lakeside cabin for thanksgiving with family. Beautiful sunsets, great location, charming house. Loved it!

Family-friendly home rentals with a pool

Top guest favorite
A comfortable living area features a gray sofa complemented by a decorative white throw pillow. Light wood flooring is covered by a patterned area rug. French doors lead to a bright dining space, with natural light filtering through nearby windows.
Home in Plymouth
4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

MarkRating, 5 stars6 months ago
Marla's vacation home was very lovely. We liked the pictures of her place, but once we arrived we realized that she had remodeled a number of rooms. Each room was updated, very clean and cozy. Marla has made sure that her place is stocked with all of the large and small conveniences that guests would want in a home away from home. The location and the surroundings are stunning, especially with the Fall foliage. One can tell that Marla takes great pride in her beautiful rental. -Mark & Susan G
Guest favorite
Home in Woodstock
4.94 out of 5 average rating, 235 reviews

Cedar Ridge: House or House+Apartment

SuzanneRating, 5 stars1 month ago
We love the house! It’s spotless (very clean), very comfortable and super peaceful in a beautiful location! Highly recommend!
Guest favorite
A welcoming living area features a large gray sectional couch with accent pillows, paired with a round coffee table. A light rug covers the dark wood floor, and a dining area with a small table and chairs is visible in the background. Natural light filters through sheer curtains.
Guest suite in Brooklyn
4.93 out of 5 average rating, 182 reviews

Affordable In-Law Apartment in Brooklyn, CT

OmarRating, 5 stars3 weeks ago
I fell in love with this apartment, the living room, kitchen, bathroom and bedroom were excellent, very cozy and endless amenities, the only complaint I have is the ceiling of the room but it is understandable and is not a big deal and they did not tell us where to put the garbage so we had to leave it in front of the door in the garage but other than that a very good experience in this beautiful place, I recommend it!
Superhost
A two-story dark wood structure is surrounded by lush greenery. The backyard features a well-maintained lawn with patches of wildflowers and a shaded area highlighted by a red umbrella atop a deck. Tall trees provide a natural canopy, creating a serene outdoor setting.
Apartment in Brooklyn
4.85 out of 5 average rating, 217 reviews

8 Bedroom, 4 full bath residence with 40' pool

JudieRating, 5 stars6 months ago
This was our first time at the Barn. There were 8 of us. We had plenty of room. Plenty of parking. MaryBeth and Doug are extremely friendly. We enjoyed hearing about the history of the Barn. Will definitely book there again next year.
Guest favorite
Home in Cotuit
4.94 out of 5 average rating, 18 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

ZackRating, 5 stars6 months ago
Perfect stay - just be sure to bring or order sheets and towels!
Superhost
The outdoor area features a pool surrounded by a wooden deck, with a shaded gazebo nearby. Two white lounge chairs are positioned along the poolside, while colorful pool floats are visible in the water. A hot tub is situated beside the gazebo, enhancing the space.
Apartment in North Falmouth
4.79 out of 5 average rating, 108 reviews

Falmouth, Cozy Studio Near Old Silver Beach

Anna GraceRating, 5 stars8 months ago
We had a wonderful weekend stay! The house is located in a quiet neighborhood and the upstairs apartment was very clean. There is quick access to local beaches and restaurants. We would stay again!
Top guest favorite
A light-filled living area features a comfortable couch adorned with yellow pillows, complemented by a blue accent chair. A wooden coffee table rests on a soft rug, surrounded by natural textures. A quilted wall hanging adds visual interest, while a small plant brings a touch of greenery.
Guesthouse in West Roxbury
4.95 out of 5 average rating, 192 reviews

Country Cottage in the City

BeckyRating, 5 stars5 months ago
Lovely place to stay, very peaceful. Mark and Merry were great hosts! Thank you very much!
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 stars10 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 Westwood

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 before taxes and fees

  • Total number of reviews

    2.6K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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