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

House rentals in Oak Bluffs

Top guest favorite
Home in Edgartown
4.96 out of 5 average rating, 68 reviews

Newly constructed home with AC , new furniture.

BillRating, 5 stars5 months ago
Again, we had a wonderful stay. The home was clean and has everything you need. Would definitely book again.
Top guest favorite
Home in Edgartown
4.97 out of 5 average rating, 226 reviews

Brand new gorgeous 2 bedroom guest house.

ArthurRating, 5 stars4 months ago
Unfortunately we had to cancel our trip because the ferry was cancelled due to weather, but I had the opportunity to interact with Debra through messages prior to our trip. She is a very kind and gracious host. I hope to be able to stay at this location during future visits to Martha’s Vineyard.
Superhost
Home in Marstons Mills
4.88 out of 5 average rating, 133 reviews

The Mills Retreat- 3BR/2Bath - Beach pass included

JulieRating, 5 stars3 months ago
This was a family Christmas getaway, and it was perfect.
Guest favorite
Home in Oak Bluffs
4.94 out of 5 average rating, 131 reviews

The Lighthouse

RandyRating, 5 stars6 months ago
Loved our stay at the vineyard. Heather's house was a perfect size and met all of our needs! We had one small problem with a toilet and it was taken care of right away. Thank you. Great place for a family. Love those dirt roads!
Top guest favorite
Home in East Falmouth
5 out of 5 average rating, 36 reviews

Spacious and immaculate custom home.

LeslieRating, 5 stars7 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 favorite
Home in Vineyard Haven
5 out of 5 average rating, 59 reviews

Well-Appointed 3 Bedrm 4 Bathrm w/ 50+ 5* Reviews

ElizabethRating, 5 stars8 months ago
Lisa is an incredible host! She was very responsive and easy to reach. The house was very clean and neat and well equipped to make your stay easy and enjoyable. You can really tell that she cares about the home and the comfort of her guests. The home is located in a very quiet lowkey neighborhood with easy access to town and everything you need either by bike or car. I would definitely stay there again.
Superhost
Home in Sandwich
4.75 out of 5 average rating, 24 reviews

Holiday in the sun!

AnthonyRating, 5 stars1 month ago
Very quiet spot. Felt comfortable staying here. very good communication, very welcoming. Thank You Craig
Guest favorite
Home in Tisbury
4.93 out of 5 average rating, 70 reviews

Classic Downtown Property

larryRating, 5 stars6 months ago
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.

Cottage rentals in Oak Bluffs

Guest favorite
Cottage in Falmouth
4.86 out of 5 average rating, 106 reviews

Spectacular Beach- front home, includes linen

RuthRating, 5 stars6 months ago
Excellent stay. Plenty of room for the 5 of us. We rested well and were able to relax. We appreciated having laundry on site since we were on a 10-day trip. The beds were comfortable and we slept well. But that is a minor detail when you can watch the sunset over the peaceful water. Lisa communicated well and responded quickly. The house is easy to get to and stores are easy to travel to. Excellent location.
Guest favorite
Cottage in Fairhaven
4.94 out of 5 average rating, 130 reviews

Seaside cottage

TomRating, 5 stars2 days ago
Comfortable place to stay, as described
Superhost
Cottage in New Seabury
4.91 out of 5 average rating, 164 reviews

Quaint Cape Cod Cottage on a Private Beach!

NancyRating, 5 stars6 months ago
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.
Superhost
Cottage in Oak Bluffs
5 out of 5 average rating, 8 reviews

The Island Collection MV: Sandy Shores

JimRating, 5 stars7 months ago
Beautiful place in the perfect location. Jolanta was extremely responsive with all my questions and a pleasure to work with. Would go back again in a heart beat!
Guest favorite
Cottage in East Falmouth
4.93 out of 5 average rating, 167 reviews

“Cozy Cottage” on Great Bay

BlythRating, 5 stars1 week ago
The perfect cottage indeed! So homey and comfortable, I had everything I needed and more. The location could not have been better, the best Air BNB experience I have ever had. Doug and Robin are lovely hosts, very responsive and so friendly. I can’t wait to come back!
Superhost
Cottage in Barnstable
4.88 out of 5 average rating, 134 reviews

Osterville Charming Cottage in the Heart of Wianno

EdwardRating, 5 stars6 months ago
Great stay at Maria’s cute little cottage by the water. Beautiful private location, perfect for kids to play in the yard.
Top guest favorite
Cottage in Tisbury
4.98 out of 5 average rating, 337 reviews

Martha's Vineyard Getaway Cottage

MitchellRating, 5 stars1 month ago
We had an amazing stay. Winter on the island is so different but still a magical place. We made a fire and just hung out while it snowed and had a fabulous Valentine’s Day. Marilyn is an awesome host - responsive, clear, and caring. One of the best stays we’ve had.
Superhost
Cottage in Pocasset
4.81 out of 5 average rating, 110 reviews

* Rustic Cape Cod Captain's Quarters Cottage

JocelynRating, 5 stars1 month ago
Wonderful place! Was completely accurate to what was shown on the listing, great place for a vacation. Super convenient to get to surrounding big towns, but the area itself was peaceful and quiet. 30 second walk to the water, and a beautiful view! Hosts were responsive and super helpful- even though we didn't stay at their place during "prime Cape Cod season", they were helpful in giving us suggestions on what we could still do during this time of year (many suggestions of which we used)! Will definitely look to stay here again in the future, maybe during the summer next time!

Condo rentals in Oak Bluffs

Top guest favorite
Condo in Tisbury
4.98 out of 5 average rating, 50 reviews

Short Walk into Town - Nice Comfortable Reasonable

AshleyRating, 5 stars8 months ago
Walkable to all local shops. Unit was clean and the kitchen was fully stocked with all items needed to prepare and enjoy a meal.
Guest favorite
Condo in Vineyard Haven
5 out of 5 average rating, 21 reviews

Relax....You're on Island Time......

JocelynRating, 5 stars7 months ago
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.
Guest favorite
Condo in Tisbury
4.91 out of 5 average rating, 47 reviews

Private 3bdrm Condo Tashmoo Woods

JamikaRating, 5 stars7 months ago
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.
Guest favorite
Condo in Tisbury
4.9 out of 5 average rating, 72 reviews

Sunny 2bedroom condo w pool, walk to town

MicheleRating, 5 stars6 months ago
We were very happy with this comfortable 2 bedroom condo. Very clean and furnished nicely. Easy walk into town for shopping and dining. We had a few questions, which Leah answered quickly and in a friendly manner. Would stay again. Thank you Leah!
Guest favorite
Condo in Oak Bluffs
4.96 out of 5 average rating, 27 reviews

LOCATION LOCATION!! Ocean- View TOP Floor Condo

TaylorRating, 5 stars7 months ago
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 :)
Superhost
Condo in Falmouth
4.69 out of 5 average rating, 13 reviews

Condo in Falmouth MA

JuanRating, 5 stars3 weeks ago
Patrick’s place was absolutely perfect! We made great use of the kitchen with no problem whatsoever. We really appreciated the nearby trail to get some fresh air and enjoyed being close to a grocery store for cooking meals. Highly recommend this place if you want a quiet laidback place to rest and refit!
Superhost
Condo in Tisbury
4.77 out of 5 average rating, 13 reviews

Martha’s Vineyard Condo * Near Ferry

AnthonyRating, 5 stars7 months ago
Great location and a nice quaint spot for one or two ! Great value for the area as well
Top guest favorite
Condo in New Seabury
4.94 out of 5 average rating, 72 reviews

Summer @ Serenity By The Sea, Mashpee , MA

GeorgeRating, 5 stars7 months ago
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.

Quick stats about vacation rentals in Oak Bluffs

  • Total rentals

    720 properties

  • Nightly prices starting at

    $40 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

Frequently Asked Questions

  • What types of vacation rentals are available in Oak Bluffs?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Oak Bluffs. From over 50 cottage rentals, over 30 condo rentals to over 440 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Where should I stay in Oak Bluffs?

    Make yourself at home in Oak Bluffs by choosing from our most frequently booked neighborhoods. We have over 670 vacation rentals in East Chop, over 670 vacation rentals in West Chop, and over 670 vacation rentals in Eastville.

  • Are there vacation rentals with a dedicated workspace in Oak Bluffs?

    Yes! Work meets play with ease at over 280 vacation rentals in Oak Bluffs featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Oak Bluffs?

    Experience the best of Oak Bluffs with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Oak Bluffs?

    Four-legged friends are welcome in Oak Bluffs. Choose from more than 170 vacation rentals for guests traveling with pets.

  • Do house rentals in Oak Bluffs have a bbq area?

    Absolutely! We offer over 250 house rentals with a bbq area in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oak Bluffs have self check-in?

    Absolutely! We offer over 160 house rentals with self check-in in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.

  • Are there Oak Bluffs house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 house rentals with pools in Oak Bluffs, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Oak Bluffs have wifi?

    Absolutely! We offer over 440 house rentals with wifi in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oak Bluffs have a gym?

    Absolutely! We offer over 30 house rentals with a gym in Oak Bluffs. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

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