Family-friendly holiday rentals in Westwood

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Westwood family-friendly rentals

Family-friendly home rentals with a hot tub

Flat in Fenway-Kenmore
4.73 out of 5 average rating, 83 reviews

Renovated 2Bed, 0.5 mile to Longwood Med Hospital

AmyRating, 5 stars1 month ago
This condo was perfect for what we needed. Just two bedrooms, a kitchen and living room, so we could relax in between walking adventures. I wish I had come across this back in the fall when my daughter was playing soccer for Northeastern because the soccer field is literally across the street. There is a nice walking trail about a quarter of a mile away. We really liked Coolidge Corners. Easy to get Ubers. The place was perfect and comfortable and easy to get in/out.
Guest favourite
Flat in South Boston
4.91 out of 5 average rating, 66 reviews

South Boston. Minutes away from Convention Center

LeeRating, 5 stars2 weeks ago
The apartment was exactly like described in an amazing location. I was attending a conference at the EXPO center, and it was an easy 25 minute walk there and back. Area is safe and clean. The best feature is the is less than a minute walk from a beautiful park and beach. Multiple Restaurants within walking distance and had no trouble getting items delivered. Would definitely stay again. Thank you so much Tanya!
Flat in Wareham
4.92 out of 5 average rating, 13 reviews

Waterfront, private, very large 2 br apt

BethuelRating, 5 stars11 months ago
Lori's place was fantastic, and she and her husband made us feel right at home from the moment we arrived. The house was amazing and very relaxing; it truly felt like home. I don't typically write reviews, but I had to because my family and I were truly amazed. We'll be recommending Lori's place to all our family and friends visiting the Cape. With Onset Beach just down the street and a short drive to the Cape, you don't have to go far to enjoy a beautiful beach.
Guest favourite
Home in Brighton
4.96 out of 5 average rating, 266 reviews

Spacious 3 bed, in unit laundry, central Air

BillRating, 5 stars3 weeks ago
We had a great stay! This house was in a great location, and very nice/spacious. We also appreciated the very thorough and clear communication regarding check-in etc, before the stay. I highly recommend Joel as a host!
Home in Sandwich
5 out of 5 average rating, 6 reviews

40 Ploughed Neck Rd

FrankRating, 5 stars11 months ago
This was a first family vacation since the kids were little. 6 adults in a very spacious home ! Could not have been better. The living room, dining room and completely modern kitchen [fully capable of any meal preparations] made for family fun and connections. The patio and fenced in yard was supurb - and the complete kitchen BBQ set-up, fire pit, fenced in yard all made for the perfect vacation. A small slice of paradise. Thank you to the Chambers family for letting us stay in your home. We were delighted and felt safe and secure in all things. Hopefully we will be able to make next year happen - amongst the future wedding plans and such ! God Bless. Frank + Cathy and the family.
Home in Gloucester
4.91 out of 5 average rating, 11 reviews

Steps to Good Harbor Beach

EllenRating, 5 stars46 months ago
This beach house worked perfectly for our stay!! The access to the beach is easy and the accommodations perfectly welcoming! The co-host could not have been more welcoming and helpful!!
Superhost
Home in Plymouth
4.85 out of 5 average rating, 82 reviews

Amazing ocean front 3 bedroom

Neil and TerriRating, 5 stars4 weeks ago
Beautiful setting with ocean views and pretty landscaping and gardens view out every window. Easily accommodated six people in our party. Home was equipped with everything we needed. Outside seating, hot tub and grill area are lovely. We had a nor’easter arrive so didn’t get to enjoy outside too much but the little that we did was incredible! Gas fireplace in living room kept dampness at bay and was just lovely. Two inside eating areas were perfect! Would come back in a heartbeat!
Superhost
Flat in Roxbury
4.78 out of 5 average rating, 329 reviews

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

YsamarRating, 5 stars2 weeks ago
Very quiet area. Close to the orange Line and multiple busses. Check In/out was easy. Apt room temp was good. Hot water was extra hot, so also a plus. Cable TV was nice.

Family- and pet-friendly home rentals

Superhost
Cottage in Sandwich
4.86 out of 5 average rating, 402 reviews

Oceanfront Cottage w/Private Beach ~ Lil’ Sea Sass

YmanRating, 5 stars1 week ago
Great stay! The place was clean, cozy, and just like the photos. The host was kind and helpful. I’d definitely stay here again.
Guest favourite
Apartment in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars3 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.
Guest favourite
Townhouse in Everett
4.91 out of 5 average rating, 253 reviews

#9 Modern Home 15 min to Boston. Relax in Style!

DawnRating, 5 stars2 weeks ago
Great place. We loved the location and the surroundings. Wally was you receptive and proactive. Everything we needed was available. The instructions and local information was great and even though we had a plan of things to do, it provided us a couple of awesome ideas for our down time. Would definitely stay there again and would recommend. Thanks Wally.
Guest favourite
Flat in Milton
4.85 out of 5 average rating, 119 reviews

Retreat Milton/Boston line (transit close) Pets

GeraldineRating, 5 stars7 months ago
We were a group of four guys on a sports-trip to Boston. The location was perfect, 30 minute drives from Downtown, Foxborough and Boston College. Lovely neighbourhood, quiet and nice walks nearby. The house was as described in the listing, plenty of space for four, clean and comfortable with a well-equipped kitchen.
Guest favourite
Townhouse in Allston
4.93 out of 5 average rating, 189 reviews

Sparkling Condo With Modern Amenities

MelissaRating, 5 stars2 weeks ago
Had a wonderful stay with my friends in Boston. The rooms and living spaces were very comfortable and clean. Michelle was very reachable and responded quickly. Would recommend this home to anyone.
Top guest favourite
Flat in Concord
4.96 out of 5 average rating, 214 reviews

Mema's Place --Lovely apartment in private home

MiebethRating, 5 stars5 days ago
We loved Ellen's place from the minute we walked in. It was warm, welcoming and had everything that we needed for a week's stay. The house/apartment is set on a quiet street set in the woods but a very close drive to Concord where we spend most of our time sightseeing. Helen's is the best restaurant to try in town. Ellen and her husband Kevin were there to welcome us and answered any concerns we had about the place. Her place is very comfortable with a large living room to relax in, a kitchen to cook in and a very comfortable bed to sleep in. I give her place 10 stars and more and I recommend it to anyone who is staying in Concord. Thank you Ellen for the wonderful stay and we look forward to seeing you again
Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 159 reviews

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

AngelaRating, 5 stars3 weeks ago
The house is amazing! It has everything that you would need and is so comfortable. The property is peaceful, and it feels like you’re on your own little island while still being minutes from stores and restaurants. We had a perfect weekend celebrating some milestone birthdays in our family.
Top guest favourite
Home in Melrose
4.96 out of 5 average rating, 110 reviews

Upscale 5BR Family Home Near Boston

DaleRating, 5 stars1 month 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

Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars42 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!
Guest favourite
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars3 weeks ago
The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.
Guest favourite
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 stars1 week ago
Brad was very friendly and helpful. Beautiful home!
Top guest favourite
Home in Plymouth
4.96 out of 5 average rating, 56 reviews

Our families slice of heaven

EmilyRating, 5 stars8 months ago
This place was INCREDIBLE!! Marla and her family were so responsive and so welcoming!! This house was the cleanest I have ever stayed in. The furniture was so comfortable and cozy. I would HIGHLY recommend staying here! I hope to come back in the near future!! Thank you Marla and family for being such amazing hosts!!
Superhost
Flat in North Falmouth
4.79 out of 5 average rating, 108 reviews

Falmouth, Cozy Studio Near Old Silver Beach

Anna GraceRating, 5 stars10 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!
Guest favourite
Guest suite in Canton
4.71 out of 5 average rating, 108 reviews

Newly renovated, close to Foxboro and Boston

StacyRating, 5 stars2 days ago
Smaranda was outside when we arrived, she greeted us and since it was around dinner time she offered some recommendations for dinner. It had been quite windy that day so the pool and hot tub had some leaves and debris in them. She was very apologetic (obviously not her fault, we can't control Mother Nature) and was very attentive and worked hard to get both the pool and hot tub ready for us to use. She showed us how everything worked and the instructions were clear and easy to follow. We used both the pool and hot tub after we got back to the space after dinner and they were both very nice and relaxing. We enjoyed our stay and everything went as planned. We would definitely stay again if Smaranda would have us! Stacy and Ray
Guest favourite
Flat in Winthrop
4.96 out of 5 average rating, 313 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

BethRating, 5 stars2 weeks ago
We had a wonderful stay! It's very close to Boston, and other area attractions like Salem and beaches, but still peaceful. We enjoyed sitting at the pool. Kathy was very responsive and checked in with us to make sure we had everything we needed. They provided clear instructions for getting into the space and I had no issues navigating in and out of the neighborhood or to the basement apartment. I would definitely stay again if I'm needing a place in the area!
Superhost
Flat in North Falmouth
4.83 out of 5 average rating, 138 reviews

Quaint North Falmouth near Old Silver Beach

NicholasRating, 5 stars10 months ago
Kim and John were great. We loved the space and anytime we communicated they were very responsive. We took advantage of the pool provided after long days at the beach and it was refreshing. We decided to stay a day longer! Thanks again!

Quick stats about holiday rentals that are family-friendly in Westwood

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹6,910 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

Destinations to explore