Beachfront holiday rentals in Dukes County

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!

WATERFRONT Cottage, Downtown w/ Beach

DIRECT WATERFRONT in-town beach house with walk-out beach and onsite private parking. This recently renovated 1 bedroom, 1.5 bath, 2-story house is located directly across the street from the famous Black Dog Tavern, right on the bustling year-round Vineyard Haven harbor. This property is no doubt one of the most unique residential properties on Martha’s Vineyard given its proximity to the harbor, ferry terminal, stores, restaurants, bike rentals, beaches & so much more. You will love it!

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.

Secluded Lagoon Front Private Beach !

Private beach, lagoon waterfront secluded location. Newly renovated (in 2026!) Pictures don't show upgrades yet! Ideal location for families that love the water and for people that love beautiful views.Tucked away on the Vineyard Haven side of the lagoon Lovely private beach, with wonderful swimming. You will not want to leave this spot. Hear the waves lap the shore from your bed. See the sunrise over the water from your bedroom. Two paddle boards included!!!

Woods Hole with views of Great Harbor.

Stunning water views in both directions. A large private backyard, Plenty of spaces to gather or have some solitude. A short walk away from Stony Beach, Woods Hole village with its various delicious restaurants, and the Martha's Vineyard Ferry. Parking in the driveway can accommodate two cars. Pets are allowed upon approval with a $50 fee. *Please see my personal reviews for previous reviews of the property. *WE ARE BOOKED ⬇️ JULY 1 - OCTOBER 1 2026

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.

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.

Cozy Waterfront Cottage, Newly Remodeled!

Beautifully upgraded WATERFRONT cottage in Menemsha with (essentially a) PRIVATE BEACH! Direct access to Vineyard Sound from your own staircase leading down to the water’s edge. Enjoy stunning sunsets and breathtaking views from every room. Private and peaceful but conveniently located just a short drive or bike ride to Menemsha or the Chilmark village center.

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.

Stunning MV Cottage on 7 acres w/ Private Beach

Enjoy nature's majesty at this classic 7 acre seaside MV escape. Sunbathe on 100 feet of private beach, explore Lake Tashmoo by kayak, read a book in the pondside hammock, have cocktails on the screened in porches, barbecue every night: make lifelong memories with your loved ones in one of the most beautiful places on earth.

Charming Falmouth Heights Steps to Beach

Prime location in Falmouth Heights!!! Steps from beloved Falmouth Heights beach, the Black Dog Café, Shipwrecked, and the finish line to the Falmouth Road Race! We are also a short walk to the Island Queen Ferry to Martha’s Vineyard, the Falmouth Yacht Club, and the delights of Falmouth’s marvelous Main Street!