Beachfront vacation rentals in South Shore

Serenity on Martha's Vineyard

This 2BR, 2 Full Bath Condo with air condition (AC) and elevator access is located across the street from State Beach (AKA the "Ink Well") in Oak Bluffs. It's on the top floor, recently redecorated, with all the amenities for a wonderful vacation. Both bedrooms have Smart TVs & AC. Free Wi-Fi. Great location, within walking distance to the ferry, beach and downtown Oak Bluffs, restaurants and shops. Car not needed! Get ready to relax and unwind. It's the perfect location! Welcome to Serenity!

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

Enjoy one of the most desirable locations on the Vineyard!! Enjoy AMAZING sunrises & gorgeous ocean views from this lovingly kept, super clean condo. Literally across the street from town beach, adjacent to Waban Park, a few blocks to Ocean Park, Flying Horses, Steamship Authority & downtown Circuit Avenue (restaurants, shops)! Bring a car (one unreserved parking spot) or walk over from the boat. Bike delivery & storage available. We hope to see you this summer in this fantastic summer condo!

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.

Nantucket Beach House with Private Beach - 6 BR

6 Queen BR, 4 ½ BA beach house. Private beach. Light-filled, open floor plan. Large deck overlooking ocean, with 2 outdoor dining areas and sitting area. Primary BR on 2nd floor has office, private BA, and 2 private decks offering sweeping views. New furniture, stove, fridge, organic mattresses & bedding. Satellite TV and internet. Outdoor shower. Renovated 2025. Large lower level with high ceilings and lots of natural light from windows & glass double door. Beach steps shared w neighbor.

The WestLake

This unique 3-level Vineyard style cottage perched on a 25' bluff offers you a panoramic view of the Lagoon's shimmering waters, and private beach access to the Nantucket Sound. From across the bay, you can see and faintly hear the Vineyard Haven Ferry departing. Simply follow the wooded path leading to over 110 feet of your own sandy beach with clean, calm waters which allows for safe kayaking and canoeing yet has the perfect breezes for windsurfing and sailing from your own mooring.

Vineyard Haven Home | 5 min to beach | 5 beds

Perfect home for one or two families looking for a summer vacation on MV. Four bedrooms and a daybed, two baths, a playroom, living room, big kitchen and big backyard with a new deck and patio. The house is situated ideally; only ten minutes walking distance to downtown Vineyard Haven, five minutes to Owen Little Beach and a short drive or walk to Tashmoo Beach. The Vineyard is our home away from home - we hope you love it. House comfortably fits 8 with room for a 9th on a daybed.

Beachfront Cottage + Studio w. Town Access

Welcome to The Rudder Cottage! Fully renovated 1930's cottage on an ocean front compound, with a picturesque porch overlooking the outer harbor, full basement with washer/dryer and central air. An additional detached studio provides a third bedroom/work space. Stunning views of the Edgartown lighthouse and Cape Poge. Access to private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

Swept Away - Madaket Beachfront

Swept Away - This beachfront cottage is the best way to experience all that Nantucket and Madaket have to offer! Just steps away from the Atlantic Ocean, with sweeping ocean views and sunsets from the second floor deck. Swept Away offers the perfect combination of modern comforts and the historic touches that make Nantucket so authentic. Beautiful original hardwood floors, tasteful furnishings, surrounding gardens, and more will make this a serene and memorable getaway.

MV Waterfront - Oak Bluffs

Marthas’s Vineyard. By the sea! Picture yourself on the deck of this waterfront home w/ private beach, sweeping views of Vineyard Sound, huge flat yard and sunsets. The house has eat-in kitchen, spacious living/dining room. Plenty of outdoor space - perfect for families, girls wknds, Derby fishermen. Comfortable seaside home w/privacy, yet convenient to Oak Bluffs and Vineyard Haven. Fully air conditioned and heated. One week minimum in summer, Friday to Friday.

Oceanfront Stay w/ 2 Double Beds (104)

This first-floor hotel room features two double beds, a kitchenette, and a prime ocean-facing location. While it offers beautiful views, the outdoor seating area of a nearby restaurant may partially obstruct them during operating hours. Part of a hotel with multiple adjoining units, this space is ideal for couples, small families, or solo travelers. Enjoy a cozy, well-equipped room just steps from the beach and attractions. A relaxing coastal retreat awaits!

As Good as it Gets-Waterfront Retreat in Falmouth

As Good As It Gets is a renovated waterfront retreat on Bourne’s Pond, just a 10-minute walk to Menauhant Beach. Relax on the expansive deck, gather by the fire pit, or kayak from the private shoreline. With a stylish kitchen, two living areas, serene bedrooms, and a peaceful wooded setting close to beaches, dining, and shopping, this home offers the perfect balance of privacy, comfort, and Cape Cod convenience for your family vacation.

Edgartown Harbor King Suite

Martha’s Vineyard has plenty of family-friendly activities, a fantastic array of dining options and much more. Situated on Edgartown Harbor among flowering English gardens, this property is ideally located on Martha's Vineyard. Guests will enjoy watching the boats come and go as they listen to the peaceful sounds of the ocean while sitting harbor side.