Beachfront vacation rentals in Oak Bluffs

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!

Lakefront~Private Beach~Cape Cod family retreat~AC

*NEW*2025 renovated waterfront retreat with private sandy beach on John’s Pond’s calm lagoon - Cape Cod’s warm, swimmable freshwater escape. Perfect for families: kayak, swim, or relax out front. Enjoy the shaded pergola lounge, perfect for outdoor dining and unwinding. Just 15 mins to South Cape & Craigville Beach, 35 to iconic Mayflower. Features open layout, AC, fast WiFi, firepit, kid gear, and gourmet kitchen. Walk to trails, minutes to Mashpee Commons, golfing. Pond days+beach adventures.

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!

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!

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!

Private Pond-side Cape Cod Home

Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

ShoestringBayHouse, waterfront & pool in Cotuit

Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. Our home overlooks the un-heated pool, beach and bay. We include: Bikes, Kayaks, and a Barnstable beach pass. Our pet friendly and spacious home with 4 BR/ 4.5 baths is priced for six (6) adult guests but our home will accommodate up to ten (10) guests at additional cost (we do not count infants/toddlers) Guest is responsible for reading the entire property description before booking

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!