Family-friendly holiday rentals in Martha's Vineyard

Arrowsmith Cottage-Oak Bluffs Near Eastville Beach

Welcome to Arrowsmith Cottage! If you are considering bringing your pet, please note - 1 small dog will be considered, but please first contact me directly (scroll down on the cottage's listing page and click on the "Contact Host" button), and tell me a little bit about him/her, as pets require homeowner's written approval and guest’s agreement to the pet fee (generally $100 per stay) and homeowners’ pet rules. Hosts are not responsible for listing inaccuracies due to Airbnb's own input or AI.

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!

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!

East Chop Cottage - walk to lighthouse & beach!

This quaint little cottage is located in the heart of East Chop, a neighborhood of Oak Bluffs. East Chop features the high, prominent bluffs that gave Oak Bluffs its name. A lighthouse, East Chop Light, stands at the north end of the chop on Telegraph Hill- only a five minute walk from the cottage. The cottage is a twelve minute walk to the harbor, and about a mile from the Oak Bluffs ferry! There is a public beach about 1/2 mile down the road. ***This space is not suitable for children

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!

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

MV King bed, Water Views, Near Bike Path- Bus stop

Have your morning coffee looking out at the sunrise and sailboats from your living room or bedroom windows. This modern studio feels secluded while only a mile and a half from Main Street Vineyard Haven, four miles from Oak Bluffs, and eight miles to Edgartown. This is the perfect place to unplug but does come equipped with everything you need, including wifi, smart tv, fully equipped kitchen, beach towels, linens, and bath towels for your stay. :)

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.

Martha's Vineyard Pied-á-terre #2 Vineyard Haven

Martha's Vineyard Pied-á-terre # 2 Vineyard Haven is but a short stroll from the ferry. Found in the heart of Vineyard Haven, this beautiful apartment is in the center of our village and it's mix of restaurants, shops, galleries and theaters. A seamless blend of comfort and convenience! If your dates are not available you can check our neighboring property Martha's Vineyard Pied-á-terre #1 Tisbury

Not Your Great Aunt's Island Cottage

In the heart Vineyard, 1930's cottage, lovingly updated by architect-owner. • Stylish decor, open floor plan, granite terrace • 2 blocks to Main St/harbor/ferry/town beach/playhouse • Central Air • Easily walkable to bike rentals, restaurants, shops, spa, library, mini-golf, etc. • Large yard with wood/gas grills, bocce, corn hole, beach chairs, fire pit • Outdoor shower • 3BR + sleeping loft

Little Lobster - King size bed

Adorable new cottage, 10 minute walk to Vineyard Haven. Wonderful, cotton soft waffle robes. Garnet Hill linens and towels. Gas grill, full kitchen with all accessories. Beautiful landscaping. Lovely farmers porch with adirondack chairs and table. Very private. Off street parking. No dogs or any pets of any kind, . Please only 2 people. Children are people!

111H Beautiful clean walk to Town, Inkwell, harbor

This elegantly decorated beach cottage is one of our favorites. It provides all the amenities for a relaxing vacation. As your host we supply beach chairs, towels and umbrella, a fully equipped kitchen, outdoor shower and entertaining space with a gas grill, WiFi, sheets and towels all within minutes of fabulous shopping, restaurants, and activities.