Beachfront holiday 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!

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!

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.

Renovated Downtown Charmer, 3 Blocks to the Beach

Welcome to your perfect Vineyard vacation retreat! Located only a short stroll to the iconic Inkwell Beach and the vibrant Circuit Avenue. You can wake up to morning coffee on the porch, then unwind in the updated living space with AC in every room, a fully stocked kitchen, modern furnishings, and coastal charm throughout. Located directly across from family-friendly Niantic Park with tennis courts, basketball courts, pickle ball and a new playground with lots of open green space.

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.

First-class 4+ BR Lagoon Pond Camp

Ultimate getaway house! Situated on Lagoon Pond in Oak Bluffs. Sleeps 10 plus 2 in the optional guest cottage. The house is under 2 miles from OB center - convenient for walking and bike riding. Beach access! The house boasts a pizza oven, outdoor nooks (hammocks!), and a spacious yard. There are amenities galore including, but not limited to: an outdoor shower, grill, board games, wifi, towels, linens, etc. 1 week min stay, Sunday turnovers in July & August.

Classic Chappy Beach House

You've heard about location, right? If you are looking for a cute, clean, place to vacation on Chappy near the water, this is it. Only a handful of homes can claim views and close proximity to Katama Bay like ours. Just walk down the yard and with a few extra steps you are at the bay. Birds come and go all day from the tidal pond in front of the house. Shaded sitting area, deck, sunsets over the Vineyard. You'll never forget the enclosed outdoor shower.

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.

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.