Vacation rentals in Oak Bluffs Harbor

Guest suite 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.

4.98 out of 5 average rating, 125 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

Guest suite in Oak Bluffs

A spacious living room is highlighted by a large grey sectional couch adorned with various throw pillows. A wooden coffee table sits in front, featuring storage compartments. Two abstract paintings in calming blues are displayed above the couch, while soft lighting illuminates the area.

4.95 out of 5 average rating, 381 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!

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.

4.94 out of 5 average rating, 201 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

4.98 out of 5 average rating, 218 reviews

An open studio space features a cozy sleeping area with a spacious bed covered in light bedding. A soft armchair and a wooden bench provide additional seating. Natural light streams in from a window, enhancing the room's bright atmosphere. Shelving displays books and decorative items.

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.

A charming cottage is framed by a lush garden with vibrant flowers. The front porch features two rocking chairs, inviting relaxation. Soft lighting emanates from inside, through the gothic-style windows, under a welcoming blue roof surrounded by greenery.

4.91 out of 5 average rating, 188 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

4.98 out of 5 average rating, 344 reviews

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

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.

A charming post and beam guest house is set amidst lush greenery, featuring an inviting entrance with a peaked roof. The landscape is softly accented by manicured shrubs and a path leading to the front door, enhancing the serene outdoor environment.

4.97 out of 5 average rating, 245 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!

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

4.92 out of 5 average rating, 273 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!

4.96 out of 5 average rating, 151 reviews

A modern kitchen features a spacious island with two black bar stools. Stainless steel appliances, including a microwave and toaster, complement quartz countertops. Natural light fills the space through large windows, revealing a glimpse of greenery outside.

Cottage in Oak Bluffs

Beautiful and walk to everything Oak Bluffs!

This is a beautiful cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.

5 out of 5 average rating, 137 reviews

The Oak Bluffs House - Walk to Beach & Town

Come stay in our home located in the ❣️ of Oak Bluffs •8 minute walk to public beach •5 minute walk to town •10 minute walk from Ferry to house, no car needed! Grocery store, Deli, Beer/Wine located just steps away from the house ! **Please Read ** Myself & my partner Max live on the property in a separate apartment on the bottom floor of the main house. We have our own entrance/exit and will NOT share any indoor spaces with you and your guests

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.

4.94 out of 5 average rating, 145 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!