Vacation rentals in Oak Bluffs

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!

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!

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!!!

We totally enjoyed our stay! Our first night we stayed out due to rain but that didn’t stop a grand time cooking at home! We had everything we needed to cook in and relax! The accommodations were perfect for the 3 of us with each of our own rooms. We enjoyed the turkeys and all their antics-lol. Thank you for a great place to stay! We will be back!

Check-in was easy. The place was very clean and well decorated. We enjoyed the backyard . Great place if you enjoy walking. Close to the grocery store and a 10-15 minute walk to Edgartown's Main street. 5 minute walk to a playground that my granddaughter thoroughly enjoyed. Beautiful and functional kitchen. Loved the hotel-like closets and how everything was labeled.

Joellen was very communicative leading up to and through the entire stay. The place was beautiful and clean. Would highly recommend!

It was a beautiful, secluded peaceful place. Kari and her family were wonderful hostesses and made us feel very welcome. Everything we needed for every day use was provided. It is not close to town; however, Uber was very handy and we figured out the bus system. My advice if you can bring a vehicle, it would be more convenient. It was also a great place for our small furry family members. Gus and Nala loved it. The outdoor space was lovely and the view was great. I got some lovely sunset pictures. There was plenty of space for everyone to relax and feel at home. I highly recommend it.

Our stay at Lisa's place was very pleasant. Her home is very nice with a lovely view of the lake and plenty of space for large families (we were only four people but can easily accommodate a few more). The neighborhood does not have a lot of car traffic which is great for walking and jogging around the lake. And it is also relatively close to Falmouth downtown and convenient stores. Lisa was very easy to communicate with and is very courteous and friendly. She really seems to care about her guests' comfortability. It was a pleasure dealing with her. Thank you, Lisa!

We highly recommend anyone coming in out of town to stay at this cottage. It’s super cozy, private, and welcoming! It’s right by the water and it’s very quiet which we loved. In addition, there are also some great under-the-radar coffee shops close by. If we come back to MA, we will definitely be looking to stay here again!

Wonderful place! Beautifully decorated. Fantastic location - easy walk to the beach. Very homey - hated to leave. Debora is a great host - very responsive to questions.

Doug and Robin were awesome! We had a nice relaxing stay and will definitely be back! Thank you!

The house is lovely! The yard is the real star here, and the location is fantastic. The only small things I would comment on are providing your own linens (not ideal) and no coffee or anything to last a day upon arrival. But overall, I would recommend it for a nice stay on the island!

We had a wonderful stay at Maria’s peaceful cottage. Nestled in a beautiful, private neighborhood, it was the perfect way to spend a long weekend away from the city. We really enjoyed waking up to her beautiful landscaping. The beach parking pass for the various neighborhood beaches and ponds is such an added bonus. The location made it easy to access Falmouth, Hyannis and other popular Cape areas. Maria is a great host, very responsive and gave clear instructions.

It is a lovely holyday flat A bit old but totally fine. More space then expected and everything needed was available.

Fantastic few days spent relaxing by the lake. Views were beautiful and the home is exactly as shown in the photos. Everything from start to finish was just right. Will definitely stay here again in the future.

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.

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 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 :)

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.

Great location and a nice quaint spot for one or two ! Great value for the area as well

Our second visit. We love the place. Quiet but close to great beaches and the Popponesset Marketplace is 2 minutes walk away, with fish restaurants and small stores with necessities (including wine and beer!). A highlight of this visit was sitting on the patio in the morning and 3 times seeing an osprey dive to the pond and catch a fish.