Vacation rentals in Oak Bluffs

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Popular amenities for Oak Bluffs vacation rentals

Stay near Oak Bluffs's top sights

Flying Horses Carousel82 locals recommend
ArtCliff Diner58 locals recommend
Lookout Tavern52 locals recommend
The Black Dog Tavern52 locals recommend
Linda Jean's Restaurant48 locals recommend
Martha's Vineyard Museum46 locals recommend

Other great vacation rentals in Oak Bluffs

Guest favourite
Home in Mattapoisett
4.89 out of 5 average rating, 9 reviews

5 Blocks to Beach+Town, Stocked Kitchen, Cozy Beds

Pei-TzuRating, 5 stars2 days ago
Lovely house and peaceful and quiet neighborhood.
Guest favourite
Vacation home in Falmouth
4.96 out of 5 average rating, 24 reviews

Fabulous Falmouth Heights home steps to beach!

KatieRating, 5 stars2 weeks ago
Beautiful home in Falmouth Heights. Plenty of room, looked just like the photos. Quiet neighborhood and a quick walk up to the beach. Plenty of space where we didn’t feel like we were on top of each other but absolutely LOVED the big couch so we could all hang out and watch movies together on the cold nights. Lesley was super responsive and accommodating to all of our needs and questions. Amazing place and host!
Guest favourite
Vacation home in Falmouth
4.92 out of 5 average rating, 52 reviews

2 Acre Waterfront Oasis Overlooking Waquoit Bay

RebeccaRating, 5 stars3 weeks ago
We had the most wonderful time here! The place was so comfortable and on a very peaceful beautiful property. We would definitely come again! It was perfect for our party of 8, sleeping and hanging and cooking and enjoying the off season quiet.
Top guest favourite
Home in East Falmouth
5 out of 5 average rating, 36 reviews

Spacious and immaculate custom home.

LeslieRating, 5 stars8 months ago
We had a fantastic family vacation in Falmouth and Anne’s house greatly exceeded all of our expectations! Comfortable, beautiful decorated and appointed with every amenity. We will be back!
Top guest favourite
Home in Woods Hole
5 out of 5 average rating, 32 reviews

Elisa's Cottage - Your Family Vacation Destination

LisaRating, 5 stars5 months ago
We had the pleasure of staying at this incredible Airbnb, and can honestly say it exceeded our expectations! From the moment we arrived, the host made us feel incredibly welcome with thoughtful touches like a personalized welcome note and a basket of local treats. Great location along with being peaceful and quiet at night. Overall, we highly recommend! The host was communicative, the space was perfect for our family of 6!
Superhost
Home in Oak Bluffs
4.81 out of 5 average rating, 108 reviews

Beautiful 3 bedroom in Oak Bluffs, walk to beach

BrendaRating, 5 stars3 weeks ago
We enjoyed our time and found the place very beautiful and well laid out. We enjoyed the board games and the large sized rooms. Angela was very helpful and gave clear instructions. It was surprising and outside of normal expectations that we were expected to wash and dry all towels and linens prior to departure I have never had to do that in an AirBnB before. It made for a bit of stress on departure. If you go, keep that in mind when planning ferry departure times. You can’t leave too early. But aside from that our stay was lovely.
Superhost
Home in Teaticket
4.8 out of 5 average rating, 25 reviews

5 Bedroom, Central Air, Close to Beaches and MORE!

CarolRating, 5 stars8 months ago
It is a nice house for a large family. We had between 8-12 there at any points. Close to beaches.
Superhost
Home in Falmouth
4.75 out of 5 average rating, 4 reviews

NEW! 2 Houses, Main House plus Guest House

CassandraRating, 5 stars8 months ago
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!

Quick stats about vacation rentals in Oak Bluffs

  • Total rentals

    720 properties

  • Nightly prices starting at

    $55 CAD before taxes and fees

  • Total number of reviews

    24K reviews

  • Family-friendly rentals

    500 properties are a good fit for families

  • Pet-friendly rentals

    170 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Dukes County
  5. Oak Bluffs