Beachfront vacation rentals in South Shore

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

Planning a family or couple's getaway to Martha's Vineyard? Then you'll love calling this delightful Oak Bluffs vacation rental your home-away-from-home. The quaint 2-bedroom, 2-bath condo offers beautiful beach views, cozy nautical decor, and a covered balcony perfect for socializing with a nice glass of wine. When it's time to explore the island, peruse the shops, restaurants, and lighthouses, or take a ride on the famous Flying Horses Carousel. A memorable Massachusetts vacation starts here!

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!

Nantucket Beach House with Private Beach - 6 BR

6 Queen BR, 4 ½ BA beach house with private beach on Nantucket. Light-filled, open floor plan. DR opens to large deck overlooking ocean, with 2 outdoor dining areas and sitting area. Primary BR on 2nd floor has private BA and office, plus 2 private decks offering sweeping views. New farmhouse DR table & chairs, LR furniture, stove, fridge. New organic mattresses & bedding. Satellite TV and internet. Outdoor shower. Renovated w/ addition 2025. Large lower level LR. Beach steps shared w neighbor.

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!

Oceanfront cottage on Surf Drive beach in Falmouth

Smell the salty air and listen to the sounds of the ocean from this renovated charming cottage - just cross the street to the beach! This 3BR, 2BA has kitchen, LR, bedrooms with sliders to patio. Home has gorgeous water views of Martha's Vineyard. 1 mile to town center with restaurants & shops, less than a mile to Shining Sea bikeway. This is a premier location in beautiful Falmouth! Please note that summer rentals are a 7-night minimum, most weeks with Saturday check-in / check-out.

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.

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!

4 bed Vineyard Haven family home 5 min to beach

Perfect home for one or two families looking for a summer vacation on MV. Four bedrooms, 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. Summer Rentals (June-Labor Day) must be a week minimum stay.

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.

Edgartown Waterfront Guesthouse

Charming guest house with spectacular views on Sengekontacket. There's a full kitchen, full bath, sitting area, and a spiral staircase that leads to a small upper bedroom where the twin beds are. The lower level has a sofa, bathroom, kitchen, queen bed, and sliding glass doors that lead onto patio , and expansive water views. There is also a separate bedroom on the first floor which was just completely redone this summer.

Humpty Dumpty - Charming Historic District Cottage

**Draft photos are posted of the in-process furniture install - professional photos are coming**. This adorable cottage is just steps away from Downtown, making it the perfect home-base for your trip to Nantucket. This 2 bedroom, 1 bath home can accommodate 5 guests. The house offers classic Nantucket architecture with coastal-inspired decor. Every inch of the house was custom made to maximize design & efficent use of space.