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.

Super responsive, great host. Very friendly, offered us the local newspaper with deals on places to go and everything. incredible space, right along the water. Thank you, Ron!

My husband and I and our small dog had a fantastic stay. Sharon accommodated a (very!) early morning checkin time and was very responsive and clear throughout our stay. The unit suited our needs well and we absolutely loved spending time in the back patio/garden area.

Our family stayed here after graduation and it was perfect

We stayed at this home with a group of five people and the home fit everyone great. The view from the home of the marsh is beautiful and we spent Saturday hanging out on the dock. It is really peaceful and we had an amazing time. Michele was a pleasure to work with and was very accommodating with being flexible for check in and check out times. Thank you again!

We visited Island Grace for a long weekend and enjoyed the many perks of this beautiful home! It was a perfect spot to visit Edgartown, Oak Bluffs, and beaches and just a short drive to other areas and towns. We enjoyed biking, the hot tub, and the well-appointed kitchen. The beds were so comfortable! We truly had everything we needed and thought it was so fun to watch their HGTV episode!

Beautiful home! David gave perfect instructions for everything about the house and was very responsive. We all had a fantastic weekend, and will definitely be booking again! Thank you David!

This is our third time staying at Bruce's place and it is as lovely as ever. Bruce has always been quick to respond to any questions and when I happened to ask ahead of time if they had a blender he ordered one which arrived when we were there! Bruce has always been incredibly thoughtful and accommodating, and our kids also love this place. It has become a tradition for us and hopefully many more to come.

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 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!

Fran's house is lovely, everything one needs for a fabulous stay. She is a very good host - responsive and informative. She lives on the prpoerty but we never saw her. We had a really great stay!!!

Very pleasant. Kristen oferred earlier checkin and very late checkout which allowed us to enjoy some additional hours at the beach and kayaking

Great little place - had everything we needed for a few nights stay with our daughter!

All I can really say is… wow!! From the moment we arrived, Liza was incredibly communicative, accommodating, and welcoming. And upon arrival, we recognized how truly special her home is; with so much character and charm! It’s very private and felt incredibly safe. The home seems nestled into Martha's Vineyard itself and the back led out to a private green space, dock, and beach with blooming bushes next to the path. This was such a rare find. It was so magical, we spent an afternoon painting watercolors of the view of the boats on the water that you can see from the living room. With six girls staying for a bachelorette weekend, we had an abundance of room. It is more spacious than the photos capture. Situated in a prime location near Edgartown. And every piece of decor, plate, bowl, cup felt vintage, special, unique. This place has authentic charm. Bottom line: Our stay was incredible. We all can’t wait to come back again!

Lianna was absolutely wonderful and a pleasure to interact with; friendly, responsive and very helpful in providing tips and guidance; the home was cosy, well located, clean and well stocked / we really enjoyed our stay

Cottage was exactly as described. Great location. We loved spending time on the porch, enjoyed the outdoor shower and all the hydrangeas were so beautiful!

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!

Our family stayed at Madi's place for our summer vacation. Madi was very responsive and communicative prior to our stay with local recommendations and instructions for the home and beach passes. Our family of 5 was comfortable and we had a wonderful time on MV. Would definitely return to Madi's place.

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!

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!

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.

Lovely location and very clean. Good spot to travel qround island. Lambert Cove was beautiful at sunset. If you have a bad back you might want to bring a mattress pad.

The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.