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Vacation rentals in Oak Bluffs

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Vacation rentals for every style

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Popular amenities for Oak Bluffs vacation rentals

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

Oak Bluffs house rentals

Top guest favorite
A bright living area features a gray sectional sofa facing large windows, allowing natural light to fill the space. The vaulted wood ceiling adds warmth, while the kitchen is equipped with stainless steel appliances and a wooden dining table, enhancing the open-concept design.
Home in Vineyard Haven
5 out of 5 average rating, 20 reviews

Family Friendly 5 BR, Walk to Town, Beach & Ferry!

Superhost
A charming cape-style house with cedar shake siding is showcased under a clear blue sky. The front entrance features a white door with sidelights, and two small windows flank the entrance. Small flower beds enhance the outdoor scene, adding subtle natural elements.
Home in Oak Bluffs
4.74 out of 5 average rating, 35 reviews

Walk to OB Town & Beach | Family & Dog Friendly

Top guest favorite
A spacious deck features two wooden Adirondack chairs facing a serene waterfront view of Vineyard Sound. Lush greenery surrounds the area, and the calm water reflects the soft hues of the sky, creating a peaceful outdoor setting.
Home in Woods Hole
4.93 out of 5 average rating, 122 reviews

Juniper Point Cottage With Ocean View

Superhost
A spacious living area is highlighted by a large blue sectional sofa, complemented by several accent pillows. Large glass doors provide a view of the deck, while pendant lights hang from a vaulted wooden ceiling, enriching the open atmosphere.
Home in Vineyard Haven
4.69 out of 5 average rating, 169 reviews

Carolyn's Vineyard Haven

Guest favorite
A three-story house is nestled within a lush green yard, showcasing two expansive outdoor decks adorned with comfortable seating. Sunlight filters through trees, creating a serene atmosphere. The lower level features walk-out access, enhancing the connection to the outdoor space surrounded by natural landscaping.
Home in Tisbury
4.98 out of 5 average rating, 276 reviews

Sunny, Spacious Vineyard Retreat

Guest favorite
A spacious living area showcases wooden flooring and high ceilings with exposed beams. Large windows fill the space with natural light, while a cozy sofa and a white coffee table invite relaxation. A kitchen area is visible in the background, providing a functional and open layout.
Home in Vineyard Haven
4.93 out of 5 average rating, 137 reviews

Vineyard Haven Walk to Ferry

Guest favorite
An inviting living room features a light-colored sofa and a natural wood coffee table. Artwork and plants add warmth, while natural light fills the space through ample windows. A large television is mounted on the wall, providing entertainment options for guests.
Home in Edgartown
5 out of 5 average rating, 28 reviews

Valentine's Retreat Hot Tub Fire Pit Trails Beach

Top guest favorite
The entrance of a condo is framed by a well-maintained lawn, with vibrant greenery and colorful flowers surrounding the doorway. The front door, featuring a decorative glass panel, opens to a sunlit pathway lined with stone pavers.
Home in Edgartown
4.99 out of 5 average rating, 156 reviews

Close to Edgartown Village Center!

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Oak Bluffs cottage rentals

Guest favorite
Large floor-to-ceiling windows frame a view of the lake, inviting natural light into the space. The open-concept living area features a comfortable seating arrangement, a dining table, and decorative elements such as floral centerpieces. Wooden beams highlight the high ceilings, enhancing the spacious feel.
Cottage in Falmouth
4.86 out of 5 average rating, 111 reviews

Spectacular Beach- front home, includes linen

Guest favorite
A charming cottage exterior is surrounded by lush greenery and blooming rose bushes, with a white picket fence enclosing the front yard. The gabled roof and shingle siding complement the tranquil landscape, offering a welcoming first impression.
Cottage in New Seabury
4.91 out of 5 average rating, 169 reviews

Quaint Cape Cod Cottage on a Private Beach!

Guest favorite
A cozy cottage is framed by lush greenery, showcasing a charming front porch with potted plants. The entrance features a black door and large windows, inviting natural light. A small dining area is visible on the side, complemented by an umbrella for shade.
Cottage in Tisbury
4.96 out of 5 average rating, 50 reviews

One Bedroom Cottage in Vineyard Haven

Top guest favorite
A bright living area features wooden beams across the ceiling and light walls. A comfortable couch with decorative pillows faces a coffee table stacked with magazines. Two lamps provide ambient lighting, while sunlight enters through multiple windows, creating a welcoming environment.
Cottage in East Falmouth
4.94 out of 5 average rating, 178 reviews

“Cozy Cottage” on Great Bay

Superhost
The charming exterior of the house features shingle siding and a welcoming porch adorned with string lights. Lush plants and blooming flowers are seen in front, while a stone border outlines the garden, creating an inviting entryway.
Cottage in Oak Bluffs
4.95 out of 5 average rating, 20 reviews

In town Cozy-Cottage-Glam w/ Fab backyard 2bd/2B

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 West Chop
4.98 out of 5 average rating, 344 reviews

Martha's Vineyard Getaway Cottage

Guest favorite
A wooden arbor frames the pathway leading to the cottage entrance, which is highlighted by a bright yellow door. Soft pink petals cover the ground, creating a charming welcome. Lush greenery surrounds the pathway, adding to the inviting atmosphere of the entryway.
Cottage in Vineyard Haven
5 out of 5 average rating, 11 reviews

Charming Cottage

Top guest favorite
The cottage features a charming yellow exterior with white trim and a red front door. A partially covered porch is visible, leading to a gravel pathway. Lush green grass surrounds the house, enhancing its inviting appearance. Trees provide a natural backdrop for the property.
Cottage in Vineyard Haven
5 out of 5 average rating, 29 reviews

Island Charmer!

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Oak Bluffs condo rentals

Superhost
A two-story home is set amid lush greenery, featuring a well-manicured lawn and a large tree offering shade. The exterior displays classic architectural elements, with white siding and black shutters. A sign marked '1846' is visible beside the pathway, inviting exploration.
Condo in Falmouth
4.88 out of 5 average rating, 24 reviews

Heart of downtown, walk to ferry, bikeway & beach!

Top guest favorite
A two-story house is depicted, featuring a light-colored exterior with multiple porches and large windows. A spacious yard is visible, framed by greenery. The porches, supported by columns, provide outdoor seating, inviting relaxation. Power lines stretch across the clear blue sky above the structure.
Condo in Vineyard Haven
4.98 out of 5 average rating, 56 reviews

Short Walk into Town - Nice Comfortable Reasonable

Guest favorite
An aerial view captures the quaint charm of the Beachside Village Resort, showcasing its coastal architecture. The vibrant green lawn is bordered by neatly trimmed shrubs, and outdoor seating areas are visible. The ocean sparkles in the background, with the road leading to the beach nearby.
Condo in Falmouth
4.86 out of 5 average rating, 7 reviews

1BR w/ Fireplace & Beach Access | Pool + Hot Tub

Superhost
A spacious pool area is enclosed by a white fence, surrounded by lush greenery. Lounge chairs are positioned around the edge of the inviting water, with trees and houses framing the scene in the background. The sky transitions to soft hues during sunset.
Condo in Vineyard Haven
4.96 out of 5 average rating, 24 reviews

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

Guest favorite
A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.
Condo in Tisbury
4.92 out of 5 average rating, 48 reviews

Private 3bdrm Condo Tashmoo Woods

Guest favorite
A two-story house is set on a lush green lawn, framed by vibrant flowering bushes. Stone steps lead up to a white front door, flanked by large windows. A partial second-floor deck is visible above the entrance, with a clear blue sky overhead.
Condo in Vineyard Haven
4.91 out of 5 average rating, 76 reviews

Sunny 2bedroom condo w pool, walk to town

Guest favorite
A light blue condominium building stands prominently along a paved road leading to the shoreline. The ocean is visible in the background, with a sandy beach accessible via a pathway. A clear blue sky enhances the serene coastal atmosphere.
Condo in Oak Bluffs
4.97 out of 5 average rating, 29 reviews

LOCATION LOCATION!! Ocean- View TOP Floor Condo

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 Vineyard Haven
4.82 out of 5 average rating, 17 reviews

Martha’s Vineyard Condo * Near Ferry

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Quick stats about vacation rentals in Oak Bluffs

  • Total rentals

    770 properties

  • Nightly prices starting at

    $40 before taxes and fees

  • Total number of reviews

    25K reviews

  • Family-friendly rentals

    540 properties are a good fit for families

  • Pet-friendly rentals

    180 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 480 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 720 vacation rentals in West Chop, over 720 vacation rentals in East Chop, and over 720 vacation rentals in Eastville.

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

    Yes! Work meets play with ease at over 300 vacation rentals in Oak Bluffs featuring dedicated workspaces. Stay connected and productive 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 180 vacation rentals for guests traveling with pets.

  • 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.

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

    Absolutely! We offer over 240 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 480 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