Vacation rentals in Oak Bluffs Harbor

The historic property is displayed from the street level, showcasing its architectural charm with a multi-story design. A covered porch is visible, featuring ornate woodwork. Shops line the street, contributing to a lively town atmosphere. Clear skies and bright sunlight enhance the inviting appearance.

4.92 out of 5 average rating, 112 reviews

Absolute Best Location on the Island

Ideal location for visitors in the middle of the most lively, diverse, fun town on Martha's Vineyard. This property is certified by the United States Department of Interior as a National Historic Property. The ferry terminal, restaurants, shops, markets, harbor, historic sites, entertainment, public transportation, and a clean sandy beach are all within minutes. A vehicle is not necessary. IF UNAVAILABLE: SIMILAR WALKABLE SISTER PROPERTY in Vineyard Haven: https://www.airbnb.com/rooms/49016488?

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, 365 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!

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.

4.98 out of 5 average rating, 206 reviews

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.

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.

4.95 out of 5 average rating, 169 reviews

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

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!

Superhost

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 serene beach scene is captured, featuring soft beige sand and gentle waves lapping at the shore. Clear blue water extends to the horizon, with a line of beach cottages visible along the coast. A clear sky enhances the tranquil atmosphere.

5 out of 5 average rating, 11 reviews

Single Occupancy Oak Bluffs Studio Apartment

Keep it simple in this peaceful studio apartment. We welcome one guest (and small dog) eager to explore all the Vineyard has to offer! Centrally located, you can easily explore Oak Bluffs or Vineyard Haven; each town is less than two miles from this natural oasis. Boasting a private entrance and stone patio, your own outdoor shower, and access to the fully fenced-in shared backyard, this apartment is perfect for one person and small dogs under 20 lbs.

The exterior of a contemporary home is showcased, featuring a mix of wood siding and large windows. Surrounding foliage and trees add natural beauty, while the architectural design emphasizes vertical elements. A deck is visible at the entrance, providing access to the inviting outdoor space.

4.93 out of 5 average rating, 134 reviews

The Lighthouse

Visit The Lighthouse! A passive solar, Bright and spacious contemporary home located in beautiful East Chop. Home is nicely appointed with 2-3 large bedrooms, 2 full baths, soaking tub. Outdoor shower and private tree lined yard with deck. Walking distance to semi private beach, town and ferry. Come relax in the window seat with a book. Have a glass of wine on the deck. Soak up the sun at the beach. This home provides true comfort!

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, 169 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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Other great vacation rentals in Oak Bluffs Harbor

A spacious balcony offers a direct view of the bustling harbor, where a ferry is seen approaching. Two wooden rocking chairs are positioned on the deck, ideal for enjoying the scenic surroundings and watching vehicles along the shore.

5 out of 5 average rating, 6 reviews

A gem on Oak Bluffs Harbor

JotakaRating, 5 stars10 months ago

amazing space, host, and vibe. would definitely reccomend this space to anyone looking for a great, clean. centrally located unit

4.68 out of 5 average rating, 142 reviews

Fantastic beach Ap 0.8 miles from Farm Neck Golf!

AntoniaRating, 5 stars8 months ago

What a lovely little flat this is. Very peaceful and beautifully decorated. Fabulous outside space as well. The linen, towels and utensils were of a good quality. lovely to have beach towels. Didn't find the sloping ceiling a problem at all. we are 6 foot and 5'9. Town is a 30 min walk we hired bikes which I highly recommend. it's an easy 10mins on a bike. Host was happy to offer us an early and late check-in and out but realise this is probably as we are now at the end ofvthe season so could be accommodated. Very kind of her thank you

A dining area features a patterned tablecloth on a large table surrounded by white chairs. Soft lighting illuminates the space, complemented by granite countertops and modern appliances in the adjoining kitchen. A window allows natural light to brighten the room.

4.92 out of 5 average rating, 61 reviews

Martha's Vineyard Apt ~ 1 Mile to Inkwell Beach!

NicholeRating, 5 stars1 week ago

We absolutely loved this spot! Quiet and tranquil, yet walking distance to shops and dining. The hosts are super sweet and communicative! This spot is a gem. Highly recommended!

A light-filled entryway opens to a wooden deck area equipped with a gas grill. A welcome mat with vibrant stripes lies on the floor, extending to a partially enclosed space. Natural light filters through the doorway, enhancing the welcoming atmosphere of the outdoor area.

4.76 out of 5 average rating, 68 reviews

Clean and Cozy Oak Bluffs Hideaway

DylanRating, 5 stars3 days ago

It was a quiet, quaint space - it has the feel of a tree house (in a good way). Everything was clean and the kitchenette had all the basics. Beach towels and beach chairs were a helpful touch. It was a nice walk from Oak Bluffs center - about 20 minutes. It was a perfect stay for us as a couple. The host was very responsive.

A coastal house is positioned by the shoreline, surrounded by small stones and pebbles. The structure features multiple levels, with a balcony overlooking the water. A quiet road runs alongside, leading into the landscape, with hints of distant houses visible in the background.

5 out of 5 average rating, 5 reviews

Private setting nestled in the heart of East Chop

RyanRating, 5 stars9 months ago

My group and our dogs had a wonderful stay at Tree Tops. The property was exactly as advertised, with plenty of indoor space and a big upper deck. John was super responsive and accommodating of our special requests as well. Would definitely stay here again.

The exterior of a traditional gingerbread home showcases a charming wraparound porch with colorful railings. Lush greenery surrounds the property, and intricate details are visible on the gabled roof. The vibrant architecture features a mix of wood and decoration, harmonizing with the natural environment.

Cottage in Oak Bluffs

4.68 out of 5 average rating, 60 reviews

Almost Paradise Charming two bedroom cottage

MichaelaRating, 5 stars3 weeks ago

Jill was extremely helpful when due to weather and ferry cancellations, we were unable to arrive on the day intended. She helped us find a hotel and very generously offered a partial refund for the night missed. This was unexpected and super helpful seeing as we needed to pay for an unplanned hotel room. The house itself, was awesome!!! Super charming and just what we needed for our stay on the island. The walk into town was easy and helpful since parking was limited in town. Overall, we had an excellent experience at Almost Paradise and can’t wait to go back someday!!

An open kitchen and dining area is visible, featuring a modern table surrounded by transparent chairs. A cozy living space can be seen in the background with natural light filtering through large windows. Warm wood flooring complements the bright, neutral tones of the cabinetry and countertops.

5 out of 5 average rating, 7 reviews

1/2 mile walk to Downtown Oak Bluffs

JamesRating, 5 stars2 days ago

We had an amazing stay at Kim’s place in Oak Bluffs for a 10-person golf trip weekend! The house was perfect for our group — spacious, clean, and packed with great amenities. We loved hanging out on the back porch, which was perfect for morning coffee or an afternoon hang out. The yard was a bonus too, giving us plenty of room for lawn games and grilling out. The location truly couldn’t be better. The house is right in the heart of Oak Bluffs and an easy walk to everything — restaurants, bars, the ferry, and all the action on Circuit Avenue. We loved being able to explore the local shops, grab food and drinks without worrying about transportation, and soak in everything Martha’s Vineyard had to offer. Additionally, the house was about a 15 minute Uber away from Edgartown so it was easy to get there as well. Kim was a fantastic host — responsive, welcoming, and made the check-in process a breeze. We highly recommend this spot for any group looking to have a fun and memorable time!

A charming dining area is featured, showcasing a round table surrounded by white, intricately designed chairs. Bright blue ceiling complements colorful floral decor on the wall. A lifebuoy and cheerful accents add character to the inviting space, with natural light illuminating the cozy atmosphere.