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

Guest favorite
A charming Cape Cod home is set within a spacious lawn, bordered by a wooden fence. Features include a neatly landscaped garden and a large garage with a double door. An American flag is displayed on the front, enhancing the welcoming appeal of the property.
Home in East Falmouth
4.93 out of 5 average rating, 130 reviews

Summer House Close To Beaches

JulieRating, 5 stars4 months ago
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.
Top guest favorite
The exterior of a newly constructed home is presented, featuring a sloped roof and two skylights. A welcoming porch extends across the front, lined with decorative lighting. Green shrubs and a gravel driveway lead up to the entrance, surrounded by trees that enhance the private setting.
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
The exterior of a newly constructed guest house is shown, featuring a spacious deck with seating arrangements. Surrounding plant beds with fresh landscaping complement the wooden structure, while a gravel pathway leads towards the entrance, creating an inviting outdoor space.
Home in Edgartown
4.97 out of 5 average rating, 227 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.
Guest favorite
The exterior of the contemporary home is depicted, featuring a natural wooden facade. A large red umbrella shades the deck, and multiple windows reflect the surrounding greenery. Steps lead up to the entrance, with well-maintained landscaping visible in the yard.
Home in Edgartown
4.88 out of 5 average rating, 26 reviews

FREE FERRY Car RESV July WK Game room Central AC

Lyons Rating, 5 stars6 months ago
We had a wonderful ti.e staying here. The house is beautiful and accommodated everyone. There is plenty to do in the area and was a nice central aarea to take in everything the island has to offer. We would love to sstay here again. Thank you so much for hhosting us!
Superhost
The exterior of the home is presented at dusk, featuring soft outdoor lighting and classic blue siding. A pathway of stone leads to the entrance, flanked by neatly manicured shrubs and a lawn. A small porch area and steps provide access to the front door.
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
A wooden deck extends from the contemporary home, featuring two Adirondack chairs positioned to overlook a serene, natural setting with vibrant autumn foliage. Sunlight filters through trees, enhancing the peaceful atmosphere of the private yard.
Home in Oak Bluffs
4.94 out of 5 average rating, 131 reviews

The Lighthouse

RandyRating, 5 stars7 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
A well-maintained exterior of a two-story home is surrounded by landscaped greenery. A stone pathway meanders through the neatly trimmed lawn, with flowering bushes and trees providing natural shade. The house features a combination of wood and shingle siding, with a small balcony visible on the upper level.
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!
Guest favorite
The exterior of the home features a blend of modern architectural styles with traditional elements. A welcoming entrance door is framed by well-maintained gardens, and the private, landscaped yard is enclosed by a white fence. A Belgian block driveway provides ample parking space.
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
An outdoor deck is visible, featuring comfortably cushioned rocking chairs facing a serene lake. Lush greenery surrounds the area, enhancing the natural ambiance and offering views of the water under clear skies.
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.
Superhost
A sandy beach stretches along the calm ocean, where gentle waves lap at the shore. Soft clouds drift in a blue sky above, while groups of people stroll along the water's edge. Coastal greenery can be seen in the background, leading up to low-lying homes.
Cottage in New Seabury
4.91 out of 5 average rating, 164 reviews

Quaint Cape Cod Cottage on a Private Beach!

NancyRating, 5 stars7 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
A charming two-story cottage features a shingled exterior with yellow trim. A white picket fence encloses the front yard, which is landscaped with greenery. Windows allow natural light to illuminate the interior. Clear blue skies and fluffy clouds provide a serene backdrop.
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
A wooden picnic table is set in a grassy area by the water, surrounded by colorful Adirondack chairs. Trees frame the scene, providing a natural backdrop with a glimpse of the calm water in the distance.
Cottage in East Falmouth
4.93 out of 5 average rating, 167 reviews

“Cozy Cottage” on Great Bay

BlythRating, 5 stars2 weeks 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
A sandy beach extends towards the horizon, bordered by gentle grasses on the left. The sky above is clear with scattered clouds, allowing sunlight to reflect off the beach surface, creating a serene and open atmosphere.
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
A cozy outdoor seating area is arranged with several white lounge chairs on a gravel surface. A brick fireplace is positioned near the house, accompanied by potted plants and a view of the deck area adorned with covered furniture in the background.
Cottage in Tisbury
4.98 out of 5 average rating, 338 reviews

Martha's Vineyard Getaway Cottage

D AnnRating, 5 stars2 weeks ago
Marilyn’s cottage was a perfect weekend getaway retreat! Although the weather was cold & rainy, the cottage was super cozy. And Marilyn was very responsive to questions. I hope to definitely return!
Guest favorite
A grassy outdoor space features two bright yellow chairs positioned invitingly in the foreground, surrounded by lush greenery. A cluster of trees provides shade, and additional seating in soft green can be seen in the background, enhancing the tranquil setting.
Cottage in Edgartown
4.98 out of 5 average rating, 97 reviews

Lovely two - story private cottage.

CarolRating, 5 stars7 months ago
We cannot say enough about this special place. Everything was perfect. It was everything we could have asked and more. This cottage has absolutely everything you would ever need. The location is wonderful. Linda has thought of everything to make you feel comfortable. She is very responsive and caring. We will definitely be back next year, already looking forward!
Guest favorite
A spacious front porch features comfortable gray seating arranged around a fire pit. String lights are installed above, adding warmth. Lush greenery can be seen in the surrounding landscape, with a view of the quiet road and neighboring properties.
Cottage in Mashpee
4.95 out of 5 average rating, 345 reviews

★The Islander | Steps From Water, Fire Pit, AC★

ChristineRating, 5 stars3 weeks ago
I cannot thank Matt and Kenzie enough for letting us use their beautiful home in Mashpee. The home was as described and they allowed us to check in early after our communication with them. I would love to stay here again. Thank you Matt and Kenzie! ❤️

Condo rentals in Oak Bluffs

Guest favorite
A modern kitchen features sleek white cabinetry and a spacious countertop. Natural light fills the area through a window, highlighting a gas stove and stainless steel appliances. A small door leads outside, while a patterned rug adds warmth to the floor.
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
A clear, inviting pool is seen with a smooth surface reflecting the sky above. Lounge chairs are arranged neatly around the pool area, with several placed alongside a white picket fence. The tranquil setting is enhanced by distant views of the horizon.
Condo in Vineyard Haven
5 out of 5 average rating, 21 reviews

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

JocelynRating, 5 stars8 months ago
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.
Guest favorite
A screened-in porch features a glass table surrounded by comfortable seating. Natural light filters through the windows, illuminating the space. The backdrop includes lush greenery, enhancing the tranquil outdoor setting.
Condo in Tisbury
4.91 out of 5 average rating, 47 reviews

Private 3bdrm Condo Tashmoo Woods

JamikaRating, 5 stars8 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
A communal unheated pool is surrounded by a white fence, featuring a spacious deck with lounge chairs. The water appears clear and inviting under a partly cloudy sky with greenery visible in the background.
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
A balcony view features two white rocking chairs beside a glass-top table, overlooking a sandy beach and clear ocean waters. A wooden pier extends into the sea, while the shoreline enjoys a serene, unobstructed vista.
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
A serene lake is shown, surrounded by lush greenery with trees reflecting gently on the calm water surface. The clear sky above features fluffy white clouds, and the sandy shore is visible in the foreground, providing a peaceful natural setting.
Condo in Falmouth
4.71 out of 5 average rating, 14 reviews

Condo in Falmouth MA

JuanRating, 5 stars1 month 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
The exterior of a cozy blue condo is shown, surrounded by green grass and trees. A wooden fence and picnic table are visible in the foreground, as well as a large tree with budding leaves. The building features multiple windows with white shutters.
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 30 condo rentals, over 440 house rentals to over 50 cottage 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
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  3. Massachusetts
  4. Dukes County
  5. Oak Bluffs