Family-friendly vacation rentals in Oak Bluffs

4.92 out of 5 average rating, 112 reviews

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.

Apartment in Oak Bluffs

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?

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, 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!

4.93 out of 5 average rating, 125 reviews

A kitchen area features a bar with three wooden stools, inviting casual dining. Hanging pots and pans are showcased above the counter, while a vase of red roses adds a touch of color. A brick wall complements the white cabinetry and appliances.

Apartment in Tisbury

Harbor view apartment, a quick walk from the ferry

This is a great one bedroom apartment on the second floor of a house. My place is close to the beach, public transport, the Steamship Authority ferry, Black Dog Tavern, Main Street Vineyard Haven, Stop & Shop grocery, and lots of great shopping. You’ll love the convenience! Walk to the apartment right off the ferry boat. Lots to do in walking distance, and onsite parking. The Martha's Vineyard Museum is a 5 minute walk, down the same street. My place is great for couples and solo adventurers.

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!

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!

Superhost

A grassy outdoor space features two blue Adirondack chairs and a small fire pit, surrounded by trees and overlooking a serene pond. A hammock hangs in the distance, while the deck is visible on the right, extending from the house.

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 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, 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!

Superhost

A spacious outdoor deck features wooden furniture, including a dining table with chairs and lounge seating. An umbrella provides shade, and potted plants enhance the natural setting. The deck is surrounded by greenery, contributing to a serene outdoor atmosphere.

Guest suite in Oak Bluffs

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!

4.93 out of 5 average rating, 121 reviews

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

Juniper Point Cottage With Ocean View

Charming Cape Cod cottage on semi-private road with and ocean view of Vineyard Sound. Renovations completed in mid-July, 2020. Three BR, 2 private attached baths, 1 semi-private bath, fully equipped kitchen, patio with BBQ grill, gas fireplace, cable-TV, WiFi internet, large second-floor deck, a/c.. Close to Vineyard Ferry, bus station and town. Seasonal rent. Please complete a reservation request to determine the rent in effect for your requested dates.

4.9 out of 5 average rating, 201 reviews

A modern kitchen is showcased, featuring dark cabinetry and granite countertops. Stainless steel appliances, including a microwave and dishwasher, are visible. A mosaic backsplash adds visual interest, while a brightly colored kettle sits atop the stove. An open doorway leads to a well-lit bathroom with framed mirrors.

Cottage in Oak Bluffs

Beautiful stroll to beach and all of downtown!

Walk to all Oak Bluffs has to offer. 5-10 Min. walk to the Harbor, Town and Inkwell Beach. Amazing location! This property is 2 minutes walk from the Gingerbread cottages. Outside there is a private patio, outdoor shower and Gas grill. Inside there is two smart Tv, Wifi, Tile floors, Marble shower, Laundry and all turn key including linens. The added bonus is this unit is brand new construction complete with new furniture and a stocked full size kitchen.

Superhost

The exterior of a charming two-story house is shown, featuring a wrap-around porch with multiple seating options. The porch is adorned with wooden chairs, and the front yard is grassy, providing ample space for outdoor relaxation. Large windows reflect natural light, contributing to the inviting ambiance.

4.82 out of 5 average rating, 110 reviews

Beautiful 3 bedroom in Oak Bluffs, walk to beach

Located in Martha's Vineyard, close to beach, bike path, oak bluffs center, art and culture, parks,and the airport. You’ll love my place because of the outdoors space with a wrap around farmers porch, the proximity to the ferry, walking distance to neighborhood beach, less than 2 miles from ferry, screened in porch, central a/c, hardwood floors and an open floor plan. Real Cape Cod feel with modern amenities. Most of my guest come back year after year!

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.