Kid-friendly holiday rentals in Dukes County

The home was clean and cozy. Updated decor and well supplied with everything we would need. I would stay again.

The house was perfect for our week on the island. The location was nice and quiet, but conveniently located within a short walking distance of everything in downtown Edgartown. Our host Claire was kind enough to suggest recommendations on some favorite locations and activities around the island. The house had everything we needed for a family of 4 and a baby. And the outdoor shower was so relaxing.

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!

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!

We really enjoyed our stay at Annemarie’s place, which was our first time on the island. It’s surrounded by lush landscape, feels secluded. Yet it is a very short drive to town (or a nice medium-long walk if you are up to it, which my wife was!). Wild turkeys often roamed the property, which was very cool. Overall great experience.

House was very cozy. Nice quiet neighborhood. Beds were very comfortable. I would not hesitate to stay there again.

Great stay, perfect for 2 people, wonderful alternative to a hotel so that we could each have our own bedrooms and great value. Matched description. Took us a minute to spot the driveway as house is tucked back from road, but super cute. You’ll want a car to be able to fully explore island easily.

Thank you Brian we enjoyed our stay. The home is beautiful and so many amenities. The rooms are large and everything was so neat and clean. The open floor plan allowed us to sit and watch TV as well as cook in that beautiful gourmet kitchen. We will be back!

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!

Paddlers Paradise is a diamond in the rough. Great location in OB just far enough from all the action. The space was well cared for and had everything we needed. Chick was responsive and kind in all her interactions as I had a bunch of questions prior to arrival. She was spot on with her island recommendations. First time staring here but won’t be my last!

Loved this place! It was right in the middle of Main St in Vineyard Haven close to the ferry, restaurants, and shops. Everything was immaculate when we got there. Gerda was very friendly and gave us some great recommendations for restaurants and things to do in the area.

I had a wonderful stay at Great Harbor Getaway. The apartment was beautiful - well decorated, excellent outdoor space, and a lovely living room and kitchen. The location of the apartment was excellent: walking distance to Town and the Morning Glory Farm. Jennifer was an excellent host: super responsive and helpful. I highly recommend Great Harbor Getaway; really looking forward to my next visit.

Martha and her place was perfect for my needs. Martha was a pleasure to talk to. She was always available and very cool. I'll be back! Thank you Martha

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!

Great stay on the vineyard! This is our fifth year coming and our first time staying with Larry. I was a little apprehensive based on location but we did not find the apartment to be loud with city life at all. Easy location just a few blocks from where we docked our boat, great balconies to relax on and they have used every inch of the apartment perfectly. The place had everything we needed for a relaxing enjoyable stay. The cleaning team was so helpful and friendly. Would recommend this stay highly

This location was excellent and the house was as described and shown in photos. A perfect place for some friends and family to have a relaxing stay.

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!

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.

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 :)