Kid-friendly holiday rentals in Oak Bluffs

We loved our stay here. It worked well for two groups. The view was amazing and we had a fair amount of wildlife visit us. Very walkable down to cure coffee shops and restaurants and also right off the bike path. Devon was a fantastic host and very accommodating! Would stay again!

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!

We loved the location at the end of a little road so no through traffic (fresh eggs next door too). The pond is fun with lots of wildlife, sometimes we could hear the roosters next door. The sunsets are lovely from the home as well. Seating in the living room great and found it to be quiet when sleeping at night. The two bedrooms on the lower level both have heat pumps (for heat/cooling) we have always had great luck with (for temperature control in the bedrooms). Loved sitting on the back deck and having the resident geese wandering around. Lovely property!

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.

This quaint location is perfect for anyone seeking a trip to Oak Bluffs. Located in a quiet neighborhood this location is quaint and easy distance from downtown OB. I would recommend this location to anyone looking to travel to OB!!

Fran and Susan's house is even more beautiful in person than in the photos. The spotlessly clean interior is thoughtfully decorated with impeccable style, and every amenity has been carefully considered to ensure a comfortable stay. It is within easy walking distance of downtown Oak Bluffs and the waterfront. Thanks to Fran for the exceptional communication and responsiveness. Cozy Bluffs made for a truly cozy escape!

This place was perfect for our mini honeymoon! Very comfortable and great location - walking distance to restaurants, shops and the beach. When our ferry was cancelled due to bad weather, the host was very responsive and we were extended an extra night. Highly recommend staying here!

Gail is super nice and the place is fun, set up well, and cozy. This is our third time here and I'm sure we'll be back!

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!

Beautiful and well-maintained place. We had a minor issue, but Jonas was very proactive in resolving it. Felt right at home.

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+ !

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 our second time at this location and it was expectedly perfect, which was why we chose it for this second visit. Great, quiet, beautiful neighborhood and perfect accommodations for our short stay. Would also be perfect for a longer stay as well!

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!

The room was perfect for our stay. Quiet and easy to get to. Nobody bothered us, the place was very quiet. Everything was clean and we enjoyed ourselves very much.

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

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

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

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!

We had a great time at Leah’s place. She is a terrific communicator, immediate responses. She also reached out to share about local fun events that were happening during our stay. So nice! We would definitely stay there again.

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.