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.

What a gorgeous location! Pet friendly, peaceful and convenient.

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!

Our family stayed here after graduation and it was perfect

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 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!

Beautiful home! David gave perfect instructions for everything about the house and was very responsive. We all had a fantastic weekend, and will definitely be booking again! Thank you David!

This is our third time staying at Bruce's place and it is as lovely as ever. Bruce has always been quick to respond to any questions and when I happened to ask ahead of time if they had a blender he ordered one which arrived when we were there! Bruce has always been incredibly thoughtful and accommodating, and our kids also love this place. It has become a tradition for us and hopefully many more to come.

Robert was friendly and very communicative regarding our stay. The house was easy to find and had essentials you would need for your stay.

This is a great place to consider staying! Rachel was wonderful from the moment of booking, until after we departed. The place is cute as can be - and as a longtime visitor of MV - this little place captures the islands vibe and unwritten codes of quality and class. If you’re browsing endless five star reviews, …believe the hype! 👍🏼 Thanks Rachel!

Olga’s house was great for our group! It was quick a 5-10 minute walk to the beach. It’s also a 5 minute drive to the Main Street in Barnstable with grocery stores and restaurants. It has a super nice backyard with tons of chairs, a fire pit, a grill, and a packed shed with fun things like cornhole. Overall it made for a fun weekend!

This home was perfect for our large family group. There are many places to gather upstairs, downstairs, on the big porch, and in the yard. The kitchen and living room are in the top floor. The kitchen has every cooking tool and pot known to humanity! We cook so this was a big plus. The home is steps from the lagoon, a deep bay on the north coast of MV. All of the bathrooms and bedrooms are on the first floor. The beds were comfortable, plenty of blankets and pillows were available. We would stay here again in a heartbeat!

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!!!

Very pleasant. Kristen oferred earlier checkin and very late checkout which allowed us to enjoy some additional hours at the beach and kayaking

It was our first time on Martha’s Vineyard and Brian made our stay well worth it. The cottage was great, just as described in the listing. It was also in a good location and very close to the harbor, restaurants etc. Having the market next door, was perfect. Brian provided tons of recommendations that were very helpful during our stay. I’ll definitely be back and I plan to book with Brian again.

I would stay at Lianna’s home a million more times! It was beautiful! I was there for a girls getaway. Beds are so comfy, plenty of places to hang out, the front and back porches are so nice to lounge! Lianna was very responsive if any questions came up. 10/10 I miss it already!

Our family stayed at Madi's place for our summer vacation. Madi was very responsive and communicative prior to our stay with local recommendations and instructions for the home and beach passes. Our family of 5 was comfortable and we had a wonderful time on MV. Would definitely return to Madi's place.

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

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!

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.

This is a big beautiful comfortable home! Pictures do not do this home the justice it deserves! Loved the home, plenty of room for 12! Terrific area. The owner was/is fantastic to work with! We would definitely rent this home again! Very large and extremely comfortable! Great location! Not far from many attractions, beaches and downtown. Has many family games and activities for your use. You definitely will not be disappointed! From renting to checking out, everything went extremely smooth! Owener is extremely helpful with any questions. you may have, and is very responsive! We, again, would absolutely rent that home again!!!

Patrick is a fantastic host and was very proactive and responsive when we ran into a problem outside anyone’s control. We would definitely recommend this home and host to others traveling to the area

We loved this house !! Everything was as described in listing and more !! Will definitely be booking with Don & Sandy again in the future.. The house was amazing! So well thought out with so much stuff for both kids and adults to do inside and outside! Pool was refreshing and they even had a pool guy come clean it during our stay which was great :) It was also very well stocked with toiletries and kitchen supplies (garbage bags, dish soap ect.) Hosts were very proactive and professional making sure that we were good and taken care of. Can’t say enough good things about our experience this stay ❤️