Family-friendly vacation rentals in Oak Bluffs

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.

Had a lovely stay here! It’s a really beautiful, charming location close to lots of great shops and restaurants.

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.

Came here for my sisters bachelorette. It was amazing . We felt right at home . It was very spacious and clean . Hosts thought of everything . Definitely would come back. The hosts were very responsive and very flexible. Great place to stay. The games and ping pong and air hockey tables were a hit !!

The house was beautiful, very comfortable and extremely well equipped. I would highly recommend this home. We had a wonderful stay there!

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

- Very good and big house, my family really liked the games room in particular, I will be back soon.

Location was great and the neighborhood was quiet and beautiful. Robert was very responsive and accommodating. The ease of finding the home & access with the great directions along with a bottle of wine in the fridge were added bonuses after driving all day/night and a late night arrival.

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!

My husband and I were transferred to a project about 30 minutes from Olga’s home. After a very long drive from WV we were pleasantly surprised. Olga’s property was exactly as described. Given we were there for an extended stay it was refreshing to find a fully stocked kitchen with high-end appliances. The master bedroom and ensuite exceeded our expectations: the room was quite large, the mattress was comfy, it offered a build in desk and private patio doors that led to the back yard. My favorite, was the very large soaking/jetted tub after a long cold day. We were overjoyed that not only did she permit dogs, she had a huge fenced in yard do”so even our Ralphie was happy. As if things could get any better we walked to the beach nearly everyday. Did i mention its only 0.2 miles away. PS: Craigsville pizza and Mexican is the bomb!!

The house is great for a group trip. It's roomy, charming, and in the perfect location if you want to walk to downtown Edgartown or use the local buses to navigate the island. The large back deck and outdoor shower were huge pluses! Nishi was kind, communicative, and offered flexibility with check-in and check-out times, which helped our travel plans run smoothly.

The place was exactly what was mentioned in photos and by the host. The host was very friendly and on spot on communication. Although we were there for a short stay, my family and I are excited to come back and stay at Kristen place again from how comfortable we felt especially how everything was so close. There were just a few minor things but it didn’t take away from how amazing Kristen was. Some recommendations I would give are the coffee maker needed a deep clean from past coffee buildup, the mop needed a replacement, the bathroom needed to be cleaned especially the shower curtain. Other than then that it was a great place and I would truly love to come back!

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!

We really enjoyed our stay the studio was exactly as described in the photos it was very comfortable lots of space for the two of us and our dog and a great location. Andrea and Tracy included a lot of extras to help make us feel right at home. We would highly recommend this rental. Thank you.

We stayed here with a large group of friends including toddlers and babies for a friend’s wedding. We loved the space, especially sitting out on the deck together, having two separate spaces so some friends could stay up chatting while the kids slept in the other house was excellent. We would highly recommend this house for a fun and relaxing group trip!

A magical spot indeed! We stayed for 4 perfect nights and we enjoyed ourselves immensely. The grounds are very pretty, with wild turkeys visiting for morning coffee. The kitchen is newly remodeled and stunning. The pool was a great find and there were plenty of nice towels and an outdoor shower. The host is lovely and the caretaker called to say hello as well so we felt very taken care of. A must visit! 10 stars!

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

Kirill is a great host, very responsive and helpful in every possible way. The best part of the house is the in-door heated pool. Kids spent hours enjoying the warm pool. Will definitely go back in the summer too!

This was our family's first visit to the Cape, and the first time that mom had been back in decades. We had a wonderful stay! Mashpee was a great location - there was local access to good beaches and restaurants; but also a great location to access Sandwich and the Canal, Falmouth, Woods Hole and the Islands, all the way to Provincetown and everything in between. And we took advantage of it all over the week we stayed. Ed was a wonderful host! From booking until we checked out, he was very communicative, friendly, and had great information about local attractions and specialties. The property was very comfortable, and big enough for our family to relax and recharge. And our son loved the heated pool! We would definitely rent this or any of Ed's properties again!

Perfect stay - just be sure to bring or order sheets and towels!

What a relaxing and wonderful stay! Barbara’s place was welcoming and even better than the pictures. The house has everything you need and the addition of the community pool was the cherry on top. The host was extremely responsive and helpful. We look forward to returning to Barbara‘s place the next time my family and I visit MV.

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!