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 Carousel23 locals recommend
ArtCliff Diner5 locals recommend
Lookout Tavern12 locals recommend
The Black Dog Tavern9 locals recommend
Linda Jean's Restaurant6 locals recommend
Martha's Vineyard Museum15 locals recommend

House rentals in Oak Bluffs

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 stars6 months ago
Again, we had a wonderful stay. The home was clean and has everything you need. Would definitely book again.
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, 134 reviews

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

AprilRating, 5 stars1 week ago
We had a great time!!! Perfect for a nice relaxing girls weekend.
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, 132 reviews

The Lighthouse

ChristopherRating, 5 stars5 months ago
Heather’s home truly is a “home away from home.” With 5+ years of visiting this peaceful and beautiful house, we look forward to planning our next visit!
Top guest favorite
A well-maintained exterior of a two-story home is surrounded by lush greenery and a manicured lawn. A gravel pathway leads to the entrance, flanked by flowering bushes, while large windows invite natural light into the living spaces.
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 favorite
A spacious home is set against a backdrop of lush trees, showcasing a unique architectural design with a multi-level roof. A wrap-around deck is visible, enhancing the outdoor space surrounded by greenery and landscaped gardens.
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.
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 stars7 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.
Guest favorite
The open living space features comfortable leather seating, a coffee table, and decorative pillows. A ceiling fan provides airflow, while natural light enters through large windows. The kitchen and dining area are visible in the background, showcasing a well-equipped space with modern appliances.
Home in Teaticket
4.93 out of 5 average rating, 122 reviews

Cute Single Family Home in Nice Neighborhood

NicoleRating, 5 stars6 months ago
This little beach oasis is such a great value! We thoroughly enjoyed our stay here. As mentioned in the description, Patty & Bruce's spot is legitimately only a few minute walk from multiple beaches and is in such a cute little neighborhood! They have plenty of beach items should you not bring your own, which is great. The space itself is perfect for a quick little weekend getaway.
Superhost
A serene view of two houses surrounded by trees on a gravel pathway. The larger house features a stone exterior and a sloped roof, while the guest house, attached to a two-car garage, showcases a light-colored facade, creating a peaceful atmosphere in the natural setting.
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!

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, 107 reviews

Spectacular Beach- front home, includes linen

LeticiaRating, 5 stars1 week ago
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!
Guest favorite
A serene waterfront scene is displayed with calm waters reflecting a clear blue sky. Green grasses and scattered stones line the shore, while small boats can be seen floating in the distance. The tranquility of nature is captured in this peaceful setting.
Cottage in Fairhaven
4.94 out of 5 average rating, 132 reviews

Seaside cottage

BethanyRating, 5 stars1 week ago
This cottage is the perfect getaway for a couple! It’s on a very quiet street and had everything you’d need to enjoy a comfortable stay. The mattress is soft and the bedroom is spacious. We had a great time! Check out Olivia’s in Fairhaven for an excellent meal! Thank you!
Guest favorite
A spacious outdoor deck is visible, furnished with a cozy seating area and umbrella. Adjoining the deck, gleaming green grass leads to white Adirondack chairs positioned for relaxation. The cottage stands in the background, softly illuminated by the setting sun.
Cottage in Fairhaven
4.89 out of 5 average rating, 37 reviews

Seaside Cottage - Steps to Beach/Close to ferry

PennyRating, 5 stars7 months ago
We LOVED our stay! Sloane’s home was a perfect place for our sister getaway! The cottage was adorable and cozy! We enjoyed having coffee in the front room, relaxing on the back deck and slept great in the beds! The neighborhood was so quiet! Just a few folks walking their dogs! 🥰 We enjoyed walking on the beach, taking the ferry for a day trip to Martha’s Vineyard, eating supper & ice cream in New Bedford and did a quick day trip to Hyannis Port! This definitely checked off our ‘Cape Cod’ bucket list! Sloane was a great host with good recommendations and quick and friendly responses! Would definitely recommend her place for a quaint getaway!
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 stars8 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
4.94 out of 5 average rating, 170 reviews

“Cozy Cottage” on Great Bay

AngelaRating, 5 stars3 days ago
Doug and Robin were awesome! We had a nice relaxing stay and will definitely be back! Thank you!
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 peaceful outdoor space is presented, featuring two lounge chairs surrounded by gravel and lush greenery. Steps lead up to the cottage, and a quiet garden area is visible in the background, offering a sense of tranquility and connection to nature.
Cottage in Tisbury
4.98 out of 5 average rating, 341 reviews

Martha's Vineyard Getaway Cottage

AllenRating, 5 stars2 weeks ago
Merilyn is super responsive and helpful hosts. She gave us very detailed instructions for check-in and checkout. Her place is truly amazing with everything we need for 5-nights stay. Both the deco and details of this vacation house are very impressive. It’s in a quiet and nice neighborhood. We really enjoyed our stay!

Condo rentals in Oak Bluffs

Superhost
A well-equipped kitchen features oak cabinets and modern stainless steel appliances, including a gas stove and refrigerator. A wooden dining table with four chairs is positioned beside the kitchen area, with light from a nearby window illuminating the space.
Condo in Barnstable
4.55 out of 5 average rating, 66 reviews

Oceanside Cottage Apt next to Craigville beach

ChrisRating, 5 stars9 months ago
Place was amazing and spacious. To bad we didn't have more time to enjoy it.
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 stars7 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 :)
Guest favorite
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
4.75 out of 5 average rating, 16 reviews

Condo in Falmouth MA

MarkRating, 5 stars4 days ago
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.
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

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 Eastville, and over 670 vacation rentals in West Chop.

  • 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