Kid-friendly holiday rentals in Dukes County

Our stay was a pleasant experience. Host messaged us a week before with instructions and a welcome email - so helpful! Communication was great. Clear check-in/check-out instructions given. Beds & bedding were very comfortable and cozy, towels were soft. Ample toilet paper and towels. Garage parking for 2 cars was helpful. Great place to stay with a family. Will rent again!

What a find! Our family gathered at Caroline and Victoria’s fantastic home this past weekend and all of us loved the place. So much space to spread out and get away from one another and lovely areas to gather as a group and socialize. The gas fireplace was a plus, and each guest or couple having their own private bathroom was key. A fantastic place for a family reunion in a wonderful town that has it all. Thank you Caroline and Victoria!

Wonderful home. Plenty of space, beautiful kitchen, comfy beds, great tv streaming choices, just a few minutes into town, and about a five minute walk to the water. Could not have asked for more. Also, having a fenced in backyard was great for my dog. Loved the place.

Off the charts wonderful! Three couples in town for a winter road race and we had a fabulous time. The house was perfect and as described… meticulously clean yet warm and inviting. We arrived early to avoid incoming bad weather and were allowed to check in a couple hours ahead of schedule. The hosts were ultra responsive. The hot tub in February was other-worldly fantastic. If you are considering a trip to the Vineyard, stay at this house! Worth every single penny!

Great weekend at Susan's place. Susan met us with the key when we arrived and gave us a quick orientation and some great recommendations for local restaurants. The house was clean, had everything we needed, and the interior wood and many windows gave it a warm, bright feel. The neighborhood was very quiet. If you don't have a car, it is about a mile walk to downtown Oak Bluffs, which we enjoyed. The back patio among the trees and outdoor shower were additional pluses. We would definitely return and hope we get a chance to do so!

Had a great time at Tom's. The place is cozy and well equipped but still close to restaurants and stores if you need them. Recieved quick responses to any concerns. Would reccomend.

Great central location to points in all directions! Very comfortable stay for a family of 5. The outdoor shower was a major plus!

nice place and nice location, near bowling and bars and restaurants. The basement was mostly unused as it does not have a bedroom. Some rooms very small where the door could not fully open. Nicely decorated and the heated floors in the main bath was a plus. Tight squeeze but our group of 7 fit.

We spent our anniversary at Leslie’s place and it was a beautiful! The views and location was like no other and we would book again! Leslie was very responsive and even left us some dinner when we came in late from the ferry. The restaurant staff were friendly and it was everything described in the listing. We didn’t want to leave!

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!

Chick's place is perfect for a Vineyard getaway! It has everything you need for 2 people and is a hop, skip and a jump away from both Vineyard Haven and Oak Bluffs town centers. It was cute, clean and cozy--- the perfect place for us to wait out the storm the ended up hitting just as we got to the Vineyard. 10/10 would stay there again!

As someone who is in the hospitality field, I can say that this place ticks all the boxes. The hosts are very hospitable, the place is pristine, and the location is peaceful and quiet. Roberto was even kind enough to help us with our bags. I highly recommend this place if you are looking for a clean quiet setting with great amenities.

Perfect experience Immaculate, well designed. Great light, comfortable bed, great location Could not have been happier on our 2 day anniversary getaway!

Great stay! Walkable to many shops and restaurants and ferry ports. Host responded very quickly and had everything you could need in the apartment. Would definitely recommend!

Mary Alice's place is so charming, equipped with everything I needed in daily life, and surrounded by full of green and peaceful neighbors. She is also very responsive and supportive in the communication. Definetely recommend, and wish to come back again!

Our initial place was actually freezing cold, with the thermostat showing 32F, the toilet tank frozen and no running water (pipes proably were frozen). It was likely the previous gueset had turned off the heat. Adam immediately responded to our questions and concerns and offered up another location which turned out to be great. We had a great time after the initial shock and thank the host for addressing the problem so quickly and effectively.

This is my third year in a row staying at one of Brian's Airbnbs. I keep returning because he is a great host. He responds quickly to questions. He provides lots of helpful things to do during your visit. And his places are very comfortable and clean.

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

To say the least this unit is better than advertised... Location, Location Location! Super clean, comfy beds, great parking...just easy!!...especially if you come in on the OB Ferry. Super convenient to all towns, but Oak Bluffs has everything and more to offer... Beach out front, super stores, excellent restaurants... We liked the Lucky Cat for dinner, Allai's for a quick hit/unique breakfast, The Overlook (maybe some of the best sushi ever!) for lunch and also dinner! Don't be overwhelmed by the waits... or the appearance of the crowds... they go fast! Heather is a spot on communicator and ready to help in any way. We look forward to a return trip!

Our stay was great. Listing was as described. Walkable to many restaurants and shops. We had trouble getting the A/C units to work but may have just been us; we made do. Appreciated the free coffee amenities as well as bottle gifted to us by the host upon arrival. Right across the road from the water and a peaceful neighborhood. Overall a very nice stay.

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

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.

We drove from Maryland up to the Cape, through lots of traffic. The host was great and responsive, suggesting great places for dinner. Our week was just amazing, wish we could have stayed longer. The pool was a perfect way to start and end the days and the bikes were a great way to explore the neighborhood. We really hope to return, just so much more we wanted to do.

We were very happy with this comfortable 2 bedroom condo. Very clean and furnished nicely. Easy walk into town for shopping and dining. We had a few questions, which Leah answered quickly and in a friendly manner. Would stay again. Thank you Leah!