Kid-friendly holiday rentals in Oak Bluffs

What a wonderful stay we had! The house was stocked with anything you could think of and the host Caroline was readily available for any questions. Will absolutely come back and recommend to all!

We really enjoyed our time at this home. The kids loved the finished basement and we had plenty of common space for two families or 4 and 5. Carrington was responsive to our needs and communicated well. The house was located close to Oak Bluffs and I enjoyed easy access to beautiful running routes by the ocean.

Our stay at this Martha’s Vineyard home was unforgettable! As a group of new friends traveling together, the space was perfect—cozy, welcoming, and just the right size for bonding over late-night chats and shared meals. The location made it easy to explore the island, with beaches, shops, and restaurants all nearby. We especially loved the outdoor area, where we spent evenings laughing under the stars. A huge bonus was discovering Tony’s Market just down the road—it had everything we needed, from snacks and fresh ingredients to local treats. The host was friendly and communicative, making sure everything went smoothly. This trip brought us all closer, and the cottage played a big part in that. Highly recommend!

This house is even more beautiful than the pictures! My family of four was able to spread out comfortably and enjoy the space. During an unexpected Nor’easter storm, we stayed in and enjoyed playing several of the games provided. Kelly’s house was perfect for our visit and I would love to stay again!

Fran's house is lovely, everything one needs for a fabulous stay. She is a very good host - responsive and informative. She lives on the prpoerty but we never saw her. We had a really great stay!!!

Lisa's place is so lovely. It is so peaceful and has a great view. Check in was super easy and everything was as expected. Lisa is a great communicator and we were easily able to get questions answered. When we had an issue (not related to our stay) Lisa was so helpful and kind. Highly recommend.

Wonderful stay at Genainna's - it was perfect for our group of eight and two dogs. The house itself is very clean and private, and close to walking paths. We will be back!

This Airbnb had everything we needed, clean and beautiful features. Location as A+ very walkable to all the best attractions of Oak Buff. John was delightful with great and easy check in and checkout. Would definitely recommend and stay again!

If I could give 100 stars I would!! Out of all the airbnbs I have stayed at Jennifer’s listing has outdone them all!! First of all, Jennifer was the most amazing host and treated us like family! Secondly, the house was spotless, not a speck could be found (and I am usually picky about cleanliness) — it was absolutely exceptional!!! I will definitely be coming back multiple times. Thank you Jennifer for hosting us!

Reda’s place was absolutely perfect for a week-long stay - I felt so at home. I was visiting family who live just down the road, but needed a space of my own to work and relax between visiting with family; it fit my needs to the “t”. The kitchen was fully stocked with all utensils (even a can opener!), so I was able to cook a great meal after a long day of work. The neighborhood is peaceful and accessible; I loved going for a run over to New Bedford and back. Reda was always around to say “hi”. My family and I will definitely be back! Thank you, Reda!

We had such a wonderful stay at Gerda's place. Great host! Gave a lot of suggestions on what to do. The apartment was very clean and beautifully decorated. I really liked the location being right on the Main St., but it can be a bit noisy in the morning with the coffee shop directly across the street. I highly recommend this place.

Monica & TJ’s listing is exactly as pictured and described. It is spotless and well appointed. The extra little touches such as quality shampoo, conditioner, shower gel (not Wally World brand), snacks, and of course the pastries upon check in- are so nice. These things tell me that they care about their guests and their experience. Great binder on the “How to use” + suggestions of things to do, restaurants, etc. Very helpful! The best part was how close to the beach this rental is! 100% would stay here again; experience to value ratio = A+ !

This was my second time staying at Chris’ place and it’s was just as nice and convenient as I remembered. Great location, efficient studio condo with everything you need. I look forward to coming back and staying there again!

We had a lovely time at Mary Alice’s place. She was incredibly kind, helpful, and responsive before, during and after our stay. Even though we weren’t able to meet in person, she made sure we felt welcomed and had what we needed. She also offered flexible checkin/checkout which we didn’t end up needing, but it was nice to have as an option! The location is a quiet and cozy neighborhood that offered us privacy but was also walkable to the main street. Many thoughtful touches incorporated into the place - I can tell that she treats her home with so much love and care, and it shows! Would recommend!

This was a great find. We very much enjoyed our stay. Place was very comfortable, clean, and location was perfect for us. I rated it 5 stars for value but would have given it a 10 if I could. Kari was very responsive and a great host.

This little apartment was a beautiful and peaceful place to stay after a long day of driving. The hosts are super friendly and eager to make your stay as comfortable as possible. I would definitely recommend this place to a friend and would stay again!

Walkable to all local shops. Unit was clean and the kitchen was fully stocked with all items needed to prepare and enjoy a meal.

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

We stayed off season, but still plenty to do and see. We loved it!

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!

Leah was the most accommodating host I’ve ever encountered. The beds were super comfortable and the house was pristine. Leah gave tons of recommendations for me and my 2 under 2. We had a great time despite the weather and I would highly recommend Leah’s place to anyone.

Heather's place is beautiful! An amazing location with close proximity to the OB steamship authority station, a number of bus lines, and the beach! The view and location are unbeatable! Heather was also super responsive in terms of coordinating flexible check-in/check-out times which was very much appreciated. Overall, would definitely recommend to anyone visiting OB :)

Great location and a nice quaint spot for one or two ! Great value for the area as well

Our second visit. We love the place. Quiet but close to great beaches and the Popponesset Marketplace is 2 minutes walk away, with fish restaurants and small stores with necessities (including wine and beer!). A highlight of this visit was sitting on the patio in the morning and 3 times seeing an osprey dive to the pond and catch a fish.