Beachfront holiday rentals in South Shore

The Loveshack, Steps to Private Waterfront

This charming cottage is a true taste of ol' cape cod. This waterfront property contains two cottages (one owner occupied) and is situated on a flat, grassy lot overlooking Great River on Monomoscoy Island, accessible by car via a short causeway, and part of a protected bird/wildlife sanctuary. This is the quintessential Cape experience - you cannot do better than this central, but yet off the beaten track, location. Walk down to the waterfront with dock & fire pit, take dip in the warm water!

Dream Vacation Premier Madaket Oceanside Retreat

Rare Madaket beachside compound for large families/groups! Have it all, a no excuses perfect getaway to a Nantucket paradise with stunning ocean views and beaches. Location-Location-Location! Steps to pristine Madaket Beach and Madaket Harbor. Enjoy surfcasting and drive on beach with your 4x4 at Smith's Point, boating or kayaking via the harbor, and much more. Millie's! Seconds to the bike path and shuttle bus to access downtown and the island. Miles of conservation land for walks/recreation.

4 Race Point-Maushop Village- 2 bedrms, 1.5 baths

Sunny and bright Maushop Village townhome, located steps from the beach stairs and path. Great view of the ocean. Ideal location, with 2 bedrooms and a full bath upstairs and central A/C. Downstairs there is a 1/2 bath, a spacious living room, patios, kitchen and dining area. There is a washer & dryer in the unit. Every amenity and necessity that you could need is provided. The furnishings and decor are Cape Cod coastal casual. Exclusively Offered by: Thurston Residential Real Estate Services

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!

Quaint Cape Cod Cottage on a Private Beach!

Create magical memories on the Cape at this sweet seaside cottage! A perfect place for a family-friendly getaway or a romantic retreat for two! The new contemporary coastal decor is cozy and comfortable and my place has all of the amenities you could want for your stay! Just steps to a beautiful beach with stunning sunsets and sunrises, cool ocean breeze, and the warm Nantucket Sound. Enjoy Popponesset Marketplace for food, shopping and fun or take a short drive to Mashpee Commons for more!

Private Beach Haven on Seconsett Island

This charming 4-bed, 2-bath Cape house on Seconsett Island is an ideal retreat for those seeking a memorable Cape Cod experience. Nestled in a perfect location, it offers breathtaking views and exclusive access to a private beach. Whether you're into activities like clam digging, kayaking, swimming in the ocean, or exploring the coastline with our powerboat. Book your stay now and embark on an unforgettable adventure. Create memories that will last a lifetime in this picturesque setting.

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!

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. Outdoor shower. Renovated and addition 2025. Beach steps shared w neighbor.

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach that is 5 min drive or 10 min bike ride or 30 min walk (walk cuts through golf course-ask host for directions).

Nantucket Style Cottage Steps from Private Beach

You will fall in love with this coastal-style designed home that is steps from a private beach. Brand new AC system, freshly painted walls, refinished floors, bathrooms on each floor, and a scenic backyard. Two balconies off each bedroom. This home has two floors and comfortably sleeps six people. A quick walk to the Popponesset Marketplace and a short drive to Mashpee Commons. See more info below!

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.