Vacation rentals in Oak Bluffs

An aerial view highlights a shoreline featuring sandy beaches and a long wooden pier extending into calm blue waters. Surrounding the area are residential homes and green landscapes, with boats visible on the water. The clear sky and vibrant hues create a scenic coastal environment.

4.99 out of 5 average rating, 115 reviews

Sea View Waterfront Beachfront Apartment

Prime location- right across the street from a sandy beach, a few minutes walk to the harbor, downtown, and transportation (boat, bus, etc). This beautiful street-level one-bedroom apartment sits across the street from the ocean, where you can take a dip and enjoy the beach. The apartment was recently redone and has a small bedroom with a queen size bed, small bathroom, full kitchen, and living room area with pull-out couch. Convenient to take the ferry into Oak Bluffs and walk to the apartment

A sliding barn door crafted from light-colored planks is viewed against a textured wood wall. The door features a black handle and a metal track, providing a modern touch. Nearby, a diamond-shaped mirror is mounted, adding visual interest to the room.

4.95 out of 5 average rating, 366 reviews

Lovely 2 BR Oak Bluffs Apartment

This 100% private apartment is on the first floor of a shared house where owners and their son live upstairs. There are no shared spaces. You have a private entrance and parking. The living room, bedrooms, bathroom, and kitchenette are bright and clean. It is exactly 1 mile from Oak Bluffs Center, a half mile from The Cottages and Farm Neck Golf Course, and a block from Tradewinds walking trails. Across the street is the bike path, & the bus stop is on the corner for easy island transportation!

4.98 out of 5 average rating, 207 reviews

A wooden deck is visible, showcasing a simple bench and a couple of potted plants. Lush green grass and a variety of trees and flowering bushes create a serene garden setting, inviting quiet moments outdoors. Light filters through the greenery, enhancing the peaceful atmosphere.

Apartment in Oak Bluffs

Sunny Studio Apartment on Martha's Vineyard

Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

4.95 out of 5 average rating, 170 reviews

A bright kitchen area is showcased, featuring tall ceilings with multiple windows allowing natural light to fill the space. Modern appliances including a stainless steel refrigerator and microwave are present, along with a granite countertop and white cabinetry. A decorative sign adds character to the room.

Apartment in Oak Bluffs

Beautiful private apartment walk to everything!

This is an incredible property! Renovated and spotless with all the amenities to make your stay feel like home, only better. Downtown Oak Bluffs and her beautiful beaches are within a five-minute walk. There is a local market and deli right next door where you can find anything you need in a pinch, and a great BBQ restaurant across the street. This second floor apartment has one bedroom with a queen-sized bed and a queen pullout couch. Smart TVs, full kitchen and laundry plus much more!

The image features a close-up of a front porch with white rocking chairs positioned on a blue painted railing. Lush greenery and vibrant flowers create a peaceful outdoor setting, while blurred colorful houses are visible in the background.

4.92 out of 5 average rating, 174 reviews

impeccable cottage STEPS to downtown OB & beach!

Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

A rustic exterior of a barn-style home features natural wood shingles and a welcoming front door. Two windows, adorned with flower-filled planters, are visible on either side, complemented by a pathway lined with smooth stones and greenery.

4.83 out of 5 average rating, 196 reviews

Waterview, Private, Walk to Beach, Mile to Town

Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

4.98 out of 5 average rating, 343 reviews

A wooden deck is shown with outdoor seating, including a table and chairs. Surrounding the deck are blooming rose bushes and lavender plants, adding vibrant colours to the natural landscape. The space is bordered by natural stone and pebbles, leading into a wooded area.

Cottage in Tisbury

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

An open kitchen area is showcased, featuring a central island with two wooden stools. Modern appliances are integrated, complemented by warm wood cabinetry and natural light streaming through nearby windows. A cozy rug lies on the wooden floor, enhancing the inviting environment.

4.97 out of 5 average rating, 240 reviews

Sweet little post and beam

A 700 sq ft post& beam guest house that sleeps 2 people. Open kitchen, living, dining area with full bath. Stairs lead to a full second story bedroom- a queen size bed, half bath, separate seating area. Private back patio and outdoor shower. Cozy off season cottage as well- radiant heat and AC. Central location to everything you want to see! Easy bike to town/beach. Very quiet and spacious. Everyone says "so much nicer in person than in the photos". Come see for yourself!

4.91 out of 5 average rating, 254 reviews

Unique Luxury Yurt w/ Free kayaking

Step into this unique yurt house! As soon as you walk in, you'll be greeted with a one-of-a-kind experience, from the textured concrete floors to the large circular skylight. Every detail is carefully planned, and you'll have the opportunity to unwind in a spacious private yard. Spend your evenings stargazing, take advantage of complimentary paddling, participate in our scheduled chicken feedings, do yoga in the roomy loft, and revel in the splendor of your exclusive island yurt!

A spacious outdoor deck area is surrounded by greenery, featuring wooden seating and a table complemented by a sun umbrella. The deck leads to a gravel pathway, accompanied by landscaped plants and a wooden fence, creating a serene outdoor atmosphere suited for relaxation.

4.78 out of 5 average rating, 318 reviews

Cottage suite between the harbors: no minimum stay

Nestled between Oak Bluffs and Vineyard Haven harbors, our relaxing suite is a perfect way to extend your weekly rental, or to enjoy a day or two on this special island we call The Rock. Our cozy guest suite, newly renovated has two bedrooms, living space, kitchenette, full bath, deck with grill, outdoor shower, and footwash (hot H20), W/D (in unit) and a private entrance. An easy walk to town and beaches. Parking is available in our driveway. Enjoy our historic home!

A well-lit staircase is visible, featuring beige carpeting with a subtle striped pattern. A wooden handrail runs along one side, leading upwards. At the top of the stairs, a framed picture is mounted on the wall, adding a touch of decoration to the space.

4.99 out of 5 average rating, 170 reviews

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

An airy lounge area features a large sectional sofa adorned with decorative pillows, arranged around a rustic coffee table. Skylights above provide natural light, illuminating the wooden beams and walls of glass that create a bright, inviting space.

4.92 out of 5 average rating, 118 reviews

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.

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Popular amenities for Oak Bluffs vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Oak Bluffs

The modern kitchen features white cabinetry and elegant quartz countertops, illuminated by vintage-style pendant lights. A large sink and gas range are included, while natural light enters through multiple windows, showcasing views of greenery outside. A wooden cutting board and knife block are positioned on the counter.

5 out of 5 average rating, 26 reviews

Vineyard Vacation, 3-Bedroom, Hot-tub, Golf course

JayneRating, 5 stars2 months ago

The home was clean and cozy. Updated decor and well supplied with everything we would need. I would stay again.

An open living area is highlighted by vaulted ceilings and exposed wooden beams. Large windows allow natural light to fill the space, while a cozy seating arrangement includes a light-colored sofa and wooden chairs. A small dining table is neatly set, enhancing the inviting atmosphere.

4.77 out of 5 average rating, 44 reviews

Tree Top Suite Get-Away

JordanRating, 5 stars2 days ago

We had a great stay at Randi’s tree top suite. The place was immaculate and nicely decorated. Perfect for two of us and our infant. The location was great, quiet and tucked away, but very close to town and beautiful beaches. Randi was very responsive the whole trip and recommended Nomans, a fun restaurant just down the road. Our trip was short this time, but would love to come back and stay at Randi’s again!

4.98 out of 5 average rating, 47 reviews

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

One Bedroom Cottage in Vineyard Haven

KeeneRating, 5 stars1 week ago

Here’s a polished review you can use for your Airbnb stay: ⸻ We had a great stay! The space was cozy in the best way—comfortable, thoughtfully laid out, and very functional. We especially loved the cool artwork and peaceful surroundings. It was an easy walk to downtown Vineyard Haven, which made everything super convenient. Check-in and check-out were seamless, and the place was spotless. Would definitely stay here again!

4.95 out of 5 average rating, 19 reviews

Cottage in Oak Bluffs

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

MorganRating, 5 stars9 months ago

The house is lovely! The yard is the real star here, and the location is fantastic. The only small things I would comment on are providing your own linens (not ideal) and no coffee or anything to last a day upon arrival. But overall, I would recommend it for a nice stay on the island!

The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.

4.93 out of 5 average rating, 199 reviews

Spectacular beach & pool combo; beautiful sunsets!

RobynRating, 5 stars1 week ago

Resort vibes with a chef's kitchen and stunning views! ***** Our stay at Larry's house was fantastic! The kitchen was absolutely amazing - spacious, modern, and fully equipped with everything we needed. We enjoyed cooking and gathering there. The real highlight was the outdoor space. The view was breathtaking! The pool and hot tub made it feel like we were staying in a private resort. Michael was helpful and responsive, making everything easy from check in to check out. We would love to come back.

A spacious outdoor deck features comfortable seating with red cushions, a low coffee table, and steps leading to a quaint yard. The home is visible in the background, showcasing a balcony. Soft lights illuminate the deck, adding to the inviting ambiance.

5 out of 5 average rating, 22 reviews

#CozyBluffs #OakBluffs Walk to Beach/Town/Ferries

CaraRating, 5 stars8 months ago

Fran and Susan's house is even more beautiful in person than in the photos. The spotlessly clean interior is thoughtfully decorated with impeccable style, and every amenity has been carefully considered to ensure a comfortable stay. It is within easy walking distance of downtown Oak Bluffs and the waterfront. Thanks to Fran for the exceptional communication and responsiveness. Cozy Bluffs made for a truly cozy escape!

4.91 out of 5 average rating, 53 reviews

A cozy cottage exterior is framed by lush greenery, highlighting natural wooden details and a shingled facade. An outdoor seating area is visible, complemented by a garden trellis adorned with blooming flowers. Bright blue skies add a sense of openness to the atmosphere.

Guesthouse in Oak Bluffs

Sweet Summer Cottage

BrennanRating, 5 stars10 months ago

Was a great place, with a convenient location.