Waterfront vacation rentals in Oak Bluffs

Beachfront Cottage

This 2-bedroom New Seabury beachfront cottage overlooks the Nantucket Sound which offers breathtaking views & a spacious patio perfect for morning coffee, barbecues, and stargazing. It is only a few steps to the private beach and a short walk to Popponesset Marketplace, the best place to grab food & drinks while enjoying live music & mini golf - quintessential Cape Cod summer living! *Popponesset Marketplace (10min walk) is closed during the off season but Mashpee Commons(10min drive) is open*

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

Welcome to our Cape house! Amazing neighborhood & the perfect spot to explore the Cape. Located on fully recreational John's Pond with your private association beach at the end of the street. Large sandy beach, boat launch, float, playground and tennis courts - plus enjoy use of our two kayaks! Just 10 min to South Cape ocean Beach & Mashpee Commons. The house is FULLY updated with hardwoods throughout, AC's, laundry room, front deck with views, private back patio with fire pit and patio.

Vineyard Cape Centrally Located Oak Bluffs, MA

Escape to this stunning 3-bedroom, 2-bath Cape-style home and enjoy 1.3 acres of privacy with breathtaking pond views. Open-concept and luxurious cathedral ceilings, gourmet kitchen brand new appliances, and spacious living room. Fabulous outdoor living and dining atop elevated deck. Luxurious primary suite with private patio, additional finished loft. Minutes to Oak Bluffs, this private retreat offers ultimate relaxation and convenience. Primary; 1 King Guest 2 Doubles Loft; 1 Double

Waterview, Private, Walk to Beach, Mile to Town

Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

Stunning Spacious Cape Cod House with Water Views

In the heart of Falmouth, Cape Cod. Elegant spacious six bedroom home with salt water views. Huge deck and a large back yard for grilling and games. Great layout and separate spaces to enjoy the house with multiple family rooms and a separate game room with a ping pong table. Close to many shops and restaurants and the best of Falmouth beaches. Conveniently located minutes from Woods Hole ferries to the islands. Close to golf, tennis courts, bike paths, Ice cream and much much more.

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!

Cottage on the Bay

Welcome to our charming Cape Cod cottage nestled on the tranquil shores of Popponessett Bay! This cozy space has been cherished by our family for generations, offering a quintessential Cape Cod experience. Located on a private point, our cottage provides stunning bay views and a serene atmosphere perfect for relaxation. Conveniently situated between Popponessett Market Place (2miles) and Mashpee Commons (2.6miles) you're close to shopping, dining, and entertainment options.

West Chop Cottage + Beach Access

Sweet, rustic, and tiny - yet comfortable with all the amenities - the cottage is a short walk to the town center, lighthouse, landmarks, and lovely harbor beaches on desirable West Chop. The private yard with harbor view allows for sunbathing and stargazing, lounging and lawn games, grilling and campfires. With access to spectacular private association ocean beach, Hancock Beach, on the island's south shore in Chilmark, this rental offers a complete Vineyard experience.

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.

Spectacular Beach- front home, includes linen

High beamed ceilings with sunny, spacious open kitchen and living room with floor to ceiling windows overlooking the lake. Oversized deck perfect for enjoying the BBQ and view with compfy rocking chairs. Minutes from quaint Falmouth village and Mashpee Commons. Planning a reunion or corporate outing? The house right next door is available for rental! Check out the following listing, "Stunning 4-bedroom Private Fresh Water Beach Front".

WATERFRONT PENTHOUSE OAK BLUFFS

3rd fl Waterfront Oak Bluffs Harbor Penthouse- Sleeps 2 comfortably-3 in a pinch. (356sqft) . Queen bed & a reclining futon couch. With kitchenette & amazing harbor views, you cannot get closer to harbor, unless you fell in. Located above a seasonal restaurant, with 5 open air restaurants (2 on each side, & were in the middle with our restaurant Lobsterville Bar & Grille below)

“Cozy Cottage” on Great Bay

Our Cozy waterfront cottage is located 120ft from great bay. Our closest beach is 2.5 miles and we are 4 miles from the center of town. Equipped with gas heat and Central A/C. We also have a gas fired fireplace to keep you cozy. Outside shower for days at the beach. We have one single kayak, two double Kayaks, a rowboat and a canoe for a scenic view of Great Bay. Quiet spot.