Waterfront holiday rentals in Oak Bluffs

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

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.

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

Welcome to our Cape house! Amazing neighborhood & the perfect spot to explore the Cape. Located on fully recreational John's Pond with your private association beach at the end of the street. Large sandy beach, boat launch, float, playground and tennis courts - plus enjoy use of our two kayaks! Just 10 min to South Cape ocean Beach & Mashpee Commons. The house is FULLY updated with hardwoods throughout, AC's, laundry room, front deck with views, private back patio with fire pit and patio.

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!

Stunning Spacious Cape Cod House with Water Views

In the heart of Falmouth, Cape Cod. Elegant spacious six bedroom home with salt water views. Huge deck and a large back yard for grilling and games. Great layout and separate spaces to enjoy the house with multiple family rooms and a separate game room with a ping pong table. Close to many shops and restaurants and the best of Falmouth beaches. Conveniently located minutes from Woods Hole ferries to the islands. Close to golf, tennis courts, bike paths, Ice cream and much much more.

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Enjoy one of THE most desirable locations on the Vineyard! Enjoy AMAZING sunrises & SPECTACULAR ocean views from this family-run, premier top floor condo. Across street from popular town beach, short walk to Ocean Park, Waban Park, Flying Horses, Steamship Authority & downtown Circuit Ave (restaurants, shops). Bring a car (one unreserved parking spot available) or walk over from boat. Bike delivery & storage available. Linens, beach towels & chairs provided. Island Paradise! ☀️🏖️

Cottage on the Bay

Welcome to our charming Cape Cod cottage nestled on the tranquil shores of Popponessett Bay! This cozy space has been cherished by our family for generations, offering a quintessential Cape Cod experience. Located on a private point, our cottage provides stunning bay views and a serene atmosphere perfect for relaxation. Conveniently situated between Popponessett Market Place (2miles) and Mashpee Commons (2.6miles) you're close to shopping, dining, and entertainment options.

West Chop Cottage + Beach Access

Sweet, rustic, and tiny - yet comfortable with all the amenities - the cottage is a short walk to the town center, lighthouse, landmarks, and lovely harbor beaches on desirable West Chop. The private yard with harbor view allows for sunbathing and stargazing, lounging and lawn games, grilling and campfires. With access to spectacular private association ocean beach, Hancock Beach, on the island's south shore in Chilmark, this rental offers a complete Vineyard experience.

Island Home. Secluded guest house in spacious yard

A secluded guest house with southern views over an expansive garden. Two blocks to downtown, the ferry, town pier and beach, restaurants, and public transportation to the rest of the island. This property is a refuge in Vineyard Haven’s historic district. Use our bikes to explore the island, or enjoy the short walk down Main Street to town beaches and fine dining. On site parking is available, or leave your car on the mainland and enjoy the easy walk from the ferry.

Private Pond-side Cape Cod Home

Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

Surf and Turf Townhouse

Cozy 2 bdr, 1.5 bath townhouse perfect for a family of four looking for an action-packed Martha's Vineyard vacation. We are located right between Oak Bluffs and Edgartown offering easy access to all down-island towns and bike paths. The development provides access to dock on Sengekontacket (where you'll find our two kayaks) a freshwater pond, and tennis/pickle ball courts for you to enjoy.

Wings Neck Lighthouse

Once in a lifetime experience to stay in a Lighthouse. Historic, unique and charming but with all of the conveniences that make a great vacation. Just feet from the Atlantic with 360 degrees of ocean view. Beautiful, peaceful and memorable all year long. Sandy private association beach just steps away. Expansive lawn and patio for enjoying salt air, waves, boats and sunsets.