Family-friendly holiday 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.

We had a girls weekend at this beautiful house. The house was amazing , clean and spacious . We loved the movie theater room , hot tub , pool table and , especially the gym. The owners were super responsive , and so friendly. We hope to come back again sometime

Not only is Ron’s place a hidden gem on Cape Cod, but he is an extraordinary thoughtful & accommodating host…the value is unmatchable, such a stellar combo of service & space! The area is perfect for your ideal vacation, and the property is truly one of a kind! You will love waking up to the ocean each day, and living in the true charm of New England simplicity. Ron will make you feel like home, and you will find a reason to be grateful every single day.

The place is great if you don't mind having to drive to a beach or to town. It's spacious and clean. And Ruth is a great host. She was very responsive.

Outstanding home and location. The pictures are nice, but do not even begin to do the home justice. Lots of space and nooks too. Very responsive owner and management. Met our every need.

This was our second time renting this property. We had a lovely adults weekend, and really enjoyed our stay.

- Very good and big house, my family really liked the games room in particular, I will be back soon.

Marina’s home is Beautiful! The home was perfect for our stay. She has everything that you would need and extra. The location was great. If it had been warmer, we would have walked to town or took the bikes out. We definitely plan on returning!

A great stay for a week with the family. Kitchen had all pots/pans needed for significant cooking, comfortable beds and linens, great walker- accessible bathroom, comfortable couches. Kathy is a very responsive host and bought a chair and DVD player for our use. Beautiful garden, bbq area and fire pit area. Note fire pit and bbq area are not wheelchair accessible. Short walk to beach and quiet neighborhood. Overall we enjoyed our time there and would recommend for a large group.

Location was great and the neighborhood was quiet and beautiful. Robert was very responsive and accommodating. The ease of finding the home & access with the great directions along with a bottle of wine in the fridge were added bonuses after driving all day/night and a late night arrival.

This was exactly what we were looking for--it was equal distant from vineyard haven and oaks bluff, right along the bus route. We ended up renting bikes and biking to and from different towns, which was amazing. Theda was extremely responsive and even let us check in and out when we needed. We'll definitely stay here again when we're in town!

This was a perfect home base for our family vacation, Olga was so friendly and quick to communicate and we loved the house so much.

The house is great for a group trip. It's roomy, charming, and in the perfect location if you want to walk to downtown Edgartown or use the local buses to navigate the island. The large back deck and outdoor shower were huge pluses! Nishi was kind, communicative, and offered flexibility with check-in and check-out times, which helped our travel plans run smoothly.

Great place, we loved it! My son didn’t want to leave. We could see the water when sitting on the living room couch, which was very pleasing! There was some issues with the cleanliness of the place, but turned out Kristen was dealing with a family health crisis. So we decided to not hold it against her. She refunded us a 100 for cleaning. We took care of all the issues to help her out a bit. There were two issues that we could not fix at the time, a moldy shower curtain, and a missing outlet faceplate which didn’t seem safe. I only mention these since we feel obligated to an honest review. We would definitely go back to this place in the future!

We stayed at Lisa’s place for three nights and it was a 10/10 experience. Lisa was a fantastic host and was very helpful with island recommendations prior to our trip. The property itself is stunning and although we wanted to explore the island, the property also provided a beautiful landscape to just relax. Even given its private, peaceful location, it was still so convenient to town. The house is an adorable converted barn that has incredible, rustic charm and the decor was so beautifully thought out. Before we even left we were talking about booking again in the future. We definitely recommend booking here!

We stayed here with a large group of friends including toddlers and babies for a friend’s wedding. We loved the space, especially sitting out on the deck together, having two separate spaces so some friends could stay up chatting while the kids slept in the other house was excellent. We would highly recommend this house for a fun and relaxing group trip!

A magical spot indeed! We stayed for 4 perfect nights and we enjoyed ourselves immensely. The grounds are very pretty, with wild turkeys visiting for morning coffee. The kitchen is newly remodeled and stunning. The pool was a great find and there were plenty of nice towels and an outdoor shower. The host is lovely and the caretaker called to say hello as well so we felt very taken care of. A must visit! 10 stars!

This place is everything you see in the pictures and more! Location is perfect - in a quiet enough neighborhood but a short walk from scenic falmouth ocean views and beaches and a short drive from downtown Falmouth for shops and restaurants. The pool is in excellent condition, clean and even though the weather didnt cooperate during our visit, the water was warm enough to enjoy even in 50 degree weather. The bedrooms are roomy and there are lots of unique cozy places to socialize for mid to large families or groups. The house is immaculately clean and Susan is perfect as a host - super responsive, prompt and flexible.

If you're looking for a house that has every modern touch and amenity, this probably isn't the place for you. If you're looking for a place where you can completely relax and take in the sounds of nature and views of the water, and have ample space to curl up with a book or stretch out, then this will work. The Gross' family house harkens back to a simpler time on the vineyard, feels rich with history, and has a multitude of spaces to enjoy as a group or by yourself. Very convenient to get to the uncrowded Philbin and Lobsterville beaches. Short drive to the sunset and lobster roll crowds at Menemsha. Kitchen was well equipped for for our party of 8. We cooked most nights and ate both inside and outside. We set up badminton outside and enjoyed the cool lap pool.

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!

Perfect stay - just be sure to bring or order sheets and towels!

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.

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.