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Vacation rentals in Oak Bluffs

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oak Bluffs vacation rentals

Self check-in
Gym
BBQ grill
Laptop-friendly workspace
Wifi

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.

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

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

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

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.

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

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

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

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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

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

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!

Superhost
A scenic coastline is visible, featuring rocky cliffs that meet a calm ocean under a partly cloudy sky. Lush green vegetation borders the sandy beach, with gentle waves lapping against the shore. The horizon stretches into the distance, creating a serene landscape.
Cottage in Oak Bluffs
5 out of 5 average rating, 8 reviews

The Island Collection MV: Sandy Shores

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

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

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, 340 reviews

Martha's Vineyard Getaway Cottage

Guest favorite
A sandy beach scene is displayed with gentle waves lapping at the shore. Tall grasses frame the left side, while a few beachgoers can be seen in the distance, enjoying the sun under a clear blue sky.
Cottage in Barnstable
4.88 out of 5 average rating, 109 reviews

Cozy Cottage - Steps to Craigville Beach

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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

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

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......

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

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

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

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

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

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Quick stats about vacation rentals in Oak Bluffs

  • Total rentals

    720 properties

  • Nightly prices starting at

    R728 ZAR 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

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  3. Massachusetts
  4. Dukes County
  5. Oak Bluffs