Family-friendly vacation rentals in Westport

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.

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.

I had a wonderful experience staying at this Airbnb. The place was exactly as described—clean, cozy, and well-stocked with all the essentials. The host was friendly, responsive, and made check-in and out super easy. The neighborhood was quiet and felt very safe, with great local spots just a short walk or drive away. I’d absolutely stay here again and recommend it to anyone looking for a comfortable and convenient stay!

Came here for a girls weekend. I think it’s even better than the photos! We had a great time!!!

This was our second time renting this property. We had a lovely adults weekend, and really enjoyed our stay.

We visited Island Grace for a long weekend and enjoyed the many perks of this beautiful home! It was a perfect spot to visit Edgartown, Oak Bluffs, and beaches and just a short drive to other areas and towns. We enjoyed biking, the hot tub, and the well-appointed kitchen. The beds were so comfortable! We truly had everything we needed and thought it was so fun to watch their HGTV episode!

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!

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!

Friendly host! Allowed us to bring our 4 little dogs! Hard to find a host that will allow this. Clean and peaceful property.

Great spot. Tons of things to do in walking distance. Cute apartment with everything you could need. Responsive and friendly host.

This was exactly what we were looking for--it was equal distant from vineyard haven and oaks bluff, right along the bus route. We ended up renting bikes and biking to and from different towns, which was amazing. Theda was extremely responsive and even let us check in and out when we needed. We'll definitely stay here again when we're in town!

This was a fabulous destination! We were looking for a big place to have a special anniversary party weekend with extended family, and this house had everything we needed. Plenty of bedrooms upstairs and first floor, many common gathering areas, large kitchen and dining room tables, and lots of Space. (And this doesn't even include the explorable property outside.) The dozens of photos in the listing were very helpful, as well as the detailed descriptions. We had specific needs for elderly relatives with disabilities, and owner Lynne was so responsive in her replies to my many messages with varied questions. Truly, Lynne, you deserve a gold star from Airbnb for promptness and offering up ways and help that made our stay both easier and fulfilling.

We had a wonderful stay with our kids and dogs. The property is in a great location - close to restaurants, shops, etc. Scott is super helpful and welcoming. The kids appreciated all the snacks! One of our favorite Airbnb stays - highly recommend and would stay again!! Thanks for everything Scott

It was our second time staying at Amanda’s beautiful cottage and we hope not the last! The space is adorable and very spacious for a couple or a couple plus a guest (which was the case on this visit). The garden is a wonderful oasis to hang out and have meals and we appreciated Amanda being flexible to allow us to bring a solo stove. The area is so rich with wildlife and Mashpee Neck and the causeway beach are the best. We had an amazing time and can’t wait to come back.

Great place. Perfect for our needs. Was equipped with everything we needed. And even had a surprise turkey visit !

We stayed at Lisa’s place for three nights and it was a 10/10 experience. Lisa was a fantastic host and was very helpful with island recommendations prior to our trip. The property itself is stunning and although we wanted to explore the island, the property also provided a beautiful landscape to just relax. Even given its private, peaceful location, it was still so convenient to town. The house is an adorable converted barn that has incredible, rustic charm and the decor was so beautifully thought out. Before we even left we were talking about booking again in the future. We definitely recommend booking here!

Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.

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

My family had a great weekend at Kristin’s house. I love this Beautiful, clean, well maintained property. The fire pit is great for marshmallow. We did not get to use the lovely pool because it got really cold at night. Bonus: filtered water from fridge, blinds + curtain, skylight in bathroom.

Barbara’s condo was roomy and comfortable. We fell in love with the screened in porch. Lovely room for a cup of coffee in the mornings and a glass of wine in the late afternoon. We took a short ride through the woods to the town beach which led us to beautiful views of Tashmoo. We had a great time!

The home was pristine, more than what we could have asked for. Shelly was an amazing host, again, more than we could have asked for. You want a gorgeous home, with a stellar host, in the cape, with a private pool, amazing amenities, on a golf course and very close to the beaches, fun spots for kids, and shops, go to this place.

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!

The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.

This place was beautiful! The kitchen was spacious and accommodated our larger group nicely. Hosts left clear instructions and proactively checked in. They were even nice enough to open their pool a little earlier so we could enjoy it. Highly recommend staying here if you are planning a girls’ weekend. Bedrooms were comfy, and everyone in my group had a lovely time. Thank you!