Kid-friendly holiday rentals in Edgartown

My family and I had a lovely stay in Oak Bluffs, MA! We loved walking around town (which is only a few minutes away on foot) and spending our time relaxing in the cottage after exploring. There are great restaurants, local shops, and beautiful scenery all within walking distance. Even though we brought our car (which was great for traveling to the island), we practically didn't need it to get around. Brianna was very responsive and accommodating during our stay. We appreciated her willingness to answer any questions and enjoyed our stay. We would love to come back!

We are a group of fishing buddies that have been coming to Chappy for many years and rented lots of places and Elaine’s home is far and away the best. From the awesome outside shower, beautiful bedrooms, high end kitchen and appliances everything one could want has been thought of.

Beautiful, large home! It was perfect for a family get-together. Very nice location and well-stocked with everything we needed. We really enjoyed having use of the bicycles in the shed and rode the bike trail near the house. The kids loved playing ping pong and foosball in the wonderful basement. The basement/game room, in particular, was a great place for my brother's toddler, who made good use of the huge variety of toys down there. We had a great time in this lovely house, thank you!

House was impeccably clean, with bathrooms and kitchen welcoming. The kitchen had everything one could need to cook and comfortably prepare meals. Overall, an excellent house - strongly recommended!

Staying at Rebecca’s Hideaway was a wonderful experience! I stayed with the family during the Thanksgiving holiday during the offseason and the location was absolutely beautiful. The hosts went above and beyond to make us feel comfortable and even left us treats at the house! The location of the house was private, but a close enough drive into downtown Edgartown to get drinks and dinner or do some shopping. There are many options to relax outdoors and it’s a close walk to get to South Beach to enjoy nature. I would definitely recommend staying here and would rebook in a heart beat!

Resort vibes with a chef's kitchen and stunning views! ***** Our stay at Larry's house was fantastic! The kitchen was absolutely amazing - spacious, modern, and fully equipped with everything we needed. We enjoyed cooking and gathering there. The real highlight was the outdoor space. The view was breathtaking! The pool and hot tub made it feel like we were staying in a private resort. Michael was helpful and responsive, making everything easy from check in to check out. We would love to come back.

Rodrigo‘s place was excellent. It is spacious and clean and has everything that you would need for a Vineyard visit. You are in someone’s backyard but it is still very quiet - except for the roosters - but even that was more charming than irritating. I would absolutely stay there again.

This is my family's second year staying here and we plan to be back. It is walkable to downtown Edgartown, near to the supermarket, relaxing, and well-appointed. The host is super-friendly and attentive, as well as responsive. Looking forward to returning!

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!

Brian was a great host. The place was immaculate and well located. Would definitely stay here again no questions asked. 10/10

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.

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.

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!

I felt very comfortable and enjoyed my time at Matt’s. The apartment was spotless, the bed was very comfortable and the entire space was very thoughtful and organized .

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!

Our stay at this Nantucket Airbnb was wonderful! The location is good — with a car a short drive to charming shops, beaches, and dining, making it easy to soak in the island’s vibe. The property was impeccably clean, well-equipped, and beautifully maintained, creating a cozy and welcoming atmosphere. The host was incredibly responsive, promptly addressing our questions and ensuring a seamless experience. It was an excellent fit for our family, with plenty of space and family-friendly amenities. Highly recommend for a memorable Nantucket getaway!

I had a wonderful stay! The space was clean, quiet, and very comfortable. Perfect for a good night’s sleep after spending the day out. I came to Dennis, MA to celebrate a friend’s birthday and used the space primarily for resting, and it was just what I needed. The heat worked well, and the check-in and check-out process was smooth and hassle-free. Overall, I really enjoyed my stay and would definitely return if I’m in the area again.

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 :)

Alex’s place was a great stay to recharge and relax after the long days we had last week. I would highly recommended this place for anyone popping through New Bedford, or staying for a few days! The airbnb was spotless and quiet and clean. I will be renting here again when I need somewhere to stay when I’m back in New Bedford! Also very close to downtown all the coffee shops, and restaurants! Quiet neighborhood.