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.

'Sconset Waterfront Cottage - "Leap O'Faith"

My place is right on Codfish Park Road just 5 steps to the beach with an unobstructed water view. It's in the best part of 'Sconset. You're a 2 minute walk to the 'Sconset Market, 'Sconset Cafe, Post Office, Claudette sandwich shop, & bus to town. We're a short walk to the Summer House restaurant, Chanticleer Restaurant, 'Sconset Casino, New Street art galleries & the Historic captains' and artists' cottages covered with roses. It's perfect for romantic vacationing or bringing the family.

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.

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.

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!

Home in West Tisbury

Introducing a captivating modern retreat nestled in the heart of West Tisbury on Martha's Vineyard. Newly built, this stunning home embodies a bold and beautiful modern design, seamlessly blending architectural elegance with contemporary luxury. With 3 bedrooms and 3 full bathrooms, as well as a spacious loft, this home offers ample space for a family or group seeking an island escape. The property is situated on 3.5-acre parcel, providing an oasis of privacy and tranquility.

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.

Mill Pond Family Retreat

🌊 Welcome to Your Cape Escape — Sleeps 7 | Falmouth, MA Your Cape escape begins here! Located in Falmouth and only a quick stroll or ride to the beach, this cozy and spacious home features a lovely view of Mill Pond. With downtown Falmouth and Woods Hole both close by, you’ll be right in the middle of classic Cape Cod beaches, dining, shops, and coastal adventures.

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.