House vacation rentals in Oak Bluffs

Prescott’s house is such a relaxing place to stay with a big group. The house has a very pretty view and is very clean and peaceful. We are very grateful for such a nice stay at this beautiful house. The BBQ outside didn’t work great but other than that we had a wonderful time! Thank you Prescott.

This house and property were charming and beautiful. The location was extremely close to beaches, restaurants, and stores all while being nestled in a quiet neighborhood. Highly recommend!

I can not say enough about how wonderful this house was to stay at for my son's wedding weekend. This house was very clean and organized. The hosts were extremely thoughtful with how everything was laid out. They thought of everything that you would need or might forget. The outdoor space was great!! My grandchildren and kids floated around the pool and played yard games. I did not hear "I am bored" and that was wonderful. We had so much space to get ready for the wedding and were able to get wonderful pictures of my son getting ready for his wedding. There are so many places in the house to either gather together or to go off and do something else. Two kids were playing chess while the younger ones were down playing with the video games and my dad and the men were watching the Masters. We had plenty of space for everyone to hang out. My entire family enjoyed this house and can't wait to go back.

We loved are family stay at Paul & Katie’s home for Easter Week. It is a dream home . The neighborhood was beautiful and walkable, with a peaceful path to a private beach. We enjoyed the shops and restaurants in Mashpee Commons about an 8 minute drive away.

This place worked out wonderfully for the 6 adults and 3 grandchildren we had with us, my 4 year old granddaughter even got her own room and loved it, along with the pool!! It was very clean and family friendly and stocked with more than we expected. There is also food and shops within walking distance. We enjoyed it immensely!! Thank you Michael, you have a wonderful place!!

We had such a fantastic stay at Sue’s beautiful Edgartown home! The house was charming, spotless, and well-stocked with everything we needed—from kids’ toys and extra keys to cozy spaces for the whole family. Even with some chilly weather, we made great memories thanks to Sue’s warmth and hospitality. One huge highlight was the car rental—what a convenient bonus! It was clean, reliable, and made exploring the island a breeze. Sue was responsive and thoughtful throughout our stay, checking in with helpful suggestions and going above and beyond. She truly made us feel at home. From shell picking at Felix Neck to relaxing in the playroom and enjoying everything the Vineyard has to offer, our family had a wonderful time. We’re already talking about our next trip back—and hoping Sue’s hot tub addition is ready by then! Highly recommend!

Beautiful house. Kid friendly Really close to the beach Amazing hosts

The house was as described and we had a great visit. We were very comfortable in the uniquely decorated rooms with interesting art and numerous books. We enjoyed the large yard, pool and garden. Our dogs had plenty of space to play and the nearby hiking trails were great.

Great location and the house has a lot of beds , which is a nice option for guests to stay in.

Our family of five loved Gary's place. Great location. Easy to walk to Oak Bluffs and very centrally located on the island. Convenient to the ferry. We appreciated all of the extra towels both beach and bathroom. Gary was very responsive and provided clear instructions. Would stay here again when we come back to the island.

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 traveled with 4 couples who have know each other since HS, 40 years ago. It was a great home to relax and catch up. The house is lovely and we loved that we each had our full bath! I highly recommend this home and this location.

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!

We loved our stay! The house was beautiful, immaculate, spacious, and well-stocked. The location was perfect, we walked into Edgartown every day, and rented bikes to get to the beach. Amy was super responsive and the house manual she provided in advance had all of the info we needed. The only downside was construction on a neighboring house— the work was noisy and a little disruptive, and large construction vehicles sometimes blocked the road getting into and out of the house. No fault of Amy’s, though, and hopefully the work will be done soon!

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.

Kenneth Is a great host communicates very well and has a genuine concern for his guests Ray

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!

This house was amazing! Beautiful and very clean! Megan had timely responses to messages and was clear in her instructions regarding the check in process. The beds were comfortable. The outdoor shower was maybe our favorite part of the trip, all the ladies enjoyed being outside and also the coolness of the inside of the house. There was tons of room. The overall aesthetic of the house was a calm, beachy vibe and made you feel like you were right beside the water. I wish we had played horseshoes in the back yard! If we need a place to stay in the future for a group trip with the ladies I would try to book here if it was available!

This was one of the nicest airbnbs that I have stayed in. The place was absolutely beautiful and so clean. The space was perfect for a weekend getaway. We had 6 girls and we had so much room. The house is perfect for entertaining with a giant JBL speaker, pool table, and amazing outdoor space. I was so impressed with all the amenities and little things Sue thought of. She was extremely responsive and was flexible with check in. This place is absolutely worth the money, I highly recommend staying here!

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!

Elizabeth is a wonderful host - responsive and friendly. The home is lovely and just a short walk from town. The living area has an open floor plan, with a well appointed kitchen and lots of comfortable living room furniture - a nice space for hanging out in the evenings. The beds are very comfortable and the bedrooms are quiet. The bathrooms were very clean and showers have great water pressure. There's a very thorough guest guide with everything you need to know about the house... heat, tv, garbage, etc... plus lots of helpful recommendations for restaurants, shopping and attractions. A great house whether you're traveling with family or friends - we felt very much at home.

Charming house, conveniently located with grocery stores, fish market with fresh fish and seafood and restaurants nearby. Kitchen generously stocked, bathrooms clean and well equipped. We had everything we needed for a short family vacation including beach chairs and towels. Kim is a great host!

We loved our stay, would definitely stay again! Meredith was very helpful and responsive. The house was beautiful and very clean. Highly recommend.