Waterfront vacation rentals in Oak Bluffs

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Top-rated waterfront rentals in Oak Bluffs

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A bright living area is showcased with large windows and a skylight, allowing natural light to fill the space. A comfortable sofa faces a circular coffee table, while woven details and coastal decor are present. Views of the water are visible through the glass doors.

Home in New Seabury

5 out of 5 average rating, 38 reviews

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*

Guest favorite

Guest suite in Oak Bluffs

4.97 out of 5 average rating, 126 reviews

Sea View Waterfront Beachfront Apartment

Prime location- right across the street from a sandy beach, a few minutes walk to the harbor, downtown, and transportation (boat, bus, etc). This beautiful street-level one-bedroom apartment sits across the street from the ocean, where you can take a dip and enjoy the beach. The apartment was recently redone and has a small bedroom with a queen size bed, small bathroom, full kitchen, and living room area with pull-out couch. Convenient to take the ferry into Oak Bluffs and walk to the apartment

Top guest favorite

The exterior of a historic home is displayed, featuring a shingle-style facade and a white front door. Lush green lawns surround the house, complemented by neatly trimmed shrubs and flowering plants. A clear sky with scattered clouds creates a serene atmosphere.

Home in Edgartown

5 out of 5 average rating, 18 reviews

Spacious Waterfront w Private Beach sleeps 10

This historic home with a private beach in Edgartown sleeps 6 in the main house and 4 in the guesthouse. Perfect for entertaining, enjoying family or reconnecting with friends. The main house has an open concept kitchen, dining room and living room with a large deck facing the water. Plenty of space to lay out and relax plus an enclosed porch for late night card games and drinks. The home is a leisurely 10 min walk into Edgartown for morning croissants at Rosewater and dinner at The Atlantic.

Top guest favorite

An enclosed front porch features multiple windows providing a view of the surrounding greenery. Two rocking chairs are positioned on a patterned rug, alongside a wooden table and lamp. Natural light fills the space, creating a bright and open atmosphere.

Home in West Tisbury

5 out of 5 average rating, 54 reviews

Renovated pond view home near Lamberts Cove beach

Idyllic renovated farmhouse across from Seth's Pond and 0.6 miles from the infamous Lamberts Cove beach. Enjoy the views from the expansive enclosed front porch, play in the 2 acre yard and relax on the back patio with hardlined gas grill. Brand new kitchen, many recent renovations and a fully stocked home ensure a comfortable stay. Terrific mid-island location with easy access to nature hikes, State Road Restaurant, the Lamberts Cove Inn Restaurant, Up Island Cronigs (groceries) and more!

Guest favorite

A private front deck features two white Adirondack chairs, positioned for relaxation. A striped towel is draped over one chair. Lush greenery surrounds the space, providing a natural backdrop, while wooden floorboards enhance the inviting outdoor area.

Home in Mashpee

4.93 out of 5 average rating, 153 reviews

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.

Guest favorite

The entrance of the Cape-style home features a welcoming front door framed by two side windows. Gray shingle siding complements the light-colored trim, while lavender plants line the walkway. A covered front porch with decorative lights provides an inviting touch.

Home in Oak Bluffs

4.97 out of 5 average rating, 30 reviews

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

Top guest favorite

A wooden dock extends over calm water, leading to a sandy beach area. Several chairs are arranged for relaxation, with a backdrop of lush greenery and a charming home in the distance. The scene conveys a serene outdoor setting surrounded by trees.

Home in Falmouth

5 out of 5 average rating, 158 reviews

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.

Guest favorite

Guesthouse in Tisbury

4.96 out of 5 average rating, 84 reviews

King bed, Water Views,AC,Near Bike Path- Bus stop

Have your morning coffee looking out at the sunrise and sailboats from your living room or bedroom windows. This modern studio feels secluded while only a mile and a half from Main Street Vineyard Haven, four miles from Oak Bluffs, and eight miles to Edgartown. This is the perfect place to unplug but does come equipped with everything you need, including wifi, smart tv, fully equipped kitchen, beach towels, linens, and bath towels for your stay.

Guest favorite

Large floor-to-ceiling windows frame a view of the lake, inviting natural light into the space. The open-concept living area features a comfortable seating arrangement, a dining table, and decorative elements such as floral centerpieces. Wooden beams highlight the high ceilings, enhancing the spacious feel.

Cottage in Falmouth

4.86 out of 5 average rating, 111 reviews

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".

Superhost

A charming waterfront building with a distinct blue facade features multiple balconies lined with railing. A lively outdoor dining area is visible on the lower level. Surrounding structures reflect a lively coastal atmosphere, with clear skies and people enjoying the vibrant setting.

Apartment in Oak Bluffs

4.88 out of 5 average rating, 163 reviews

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)

Top guest favorite

A cozy living area features a comfortable gray sofa adorned with coral patterns, a light blue accent chair, and a white coffee table. Natural light floods the space through a door leading to the outdoors, while decorative wall art enhances the welcoming atmosphere.

Cottage in East Falmouth

4.94 out of 5 average rating, 189 reviews

“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.

Guest favorite

A waterfront Cape Cod home is surrounded by green grass and trees. A wrap-around deck is visible, along with a fire pit and several white outdoor chairs arranged in a circle. Kayaks and a picnic table are prominently placed near the water.

Home in Mashpee

4.95 out of 5 average rating, 194 reviews

Gorgeous Sunsets! Private family beach!

Saturday to Saturday weekly rental during summer months. Wrap around deck, beach and waterfront. Open layout. Perfect for families & Couples with a family beach . Stunning sunsets, very private and close to Mashpee commons, Falmouth and New Seabury all 10 minutes away. We are happy to have you for stays longer than 7 days! Just send us a note!