Beachfront holiday rental in Oak Bluffs

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Top-rated beachfront accommodation in Oak Bluffs

Guests agree: These beachfront homes are highly rated for location, cleanliness and more.

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Top Guest favourite
A bright living area features a light-colored sofa adorned with decorative pillows, positioned beneath a wooden 'LAKE HOUSE' sign. Large windows provide views of the water and trees, while a side table with a lamp and a vintage dresser complete the welcoming space.
Home in Mashpee
5 out of 5 average rating, 24 reviews

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.

Superhost
A scenic view of the ocean is presented, with a sandy beach stretching along the shore under a clear blue sky. The sun's reflection on the water sparkles, while coastal vegetation lines the sandy area. The horizon meets the gentle waves, creating a tranquil atmosphere.
Home in New Seabury
5 out of 5 average rating, 5 reviews

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

Guest favourite
A charming cottage exterior is surrounded by lush greenery and blooming rose bushes, with a white picket fence enclosing the front yard. The gabled roof and shingle siding complement the tranquil landscape, offering a welcoming first impression.
Cottage in New Seabury
4.9 out of 5 average rating, 178 reviews

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!

Guest favourite
A sandy path leads to the tranquil shoreline, bordered by patches of grass and smooth stones. The calm blue waters stretch toward the horizon, with scattered rocks visible along the shore. A clear sky is filled with fluffy clouds, enhancing the serene coastal atmosphere.
Cottage in Mattapoisett
4.86 out of 5 average rating, 35 reviews

Comfy beach house in Mattapoisett

Get your Vitamin Sea here! This timeless two-story beach cottage retains its original woodwork and hardwood floors, but many upgrades make for a comfy and convenient vacation. Outdoor shower? Yeah, we got that! Fully equipped kitchen? Yes! Crescent Beach is a small neighborhood in a very desirable seaside town. Two sunny, spacious bedrooms are located upstairs, and the kitchen and bathroom are downstairs. It's a short stroll down to the sandy and private association beach on Buzzards Bay.

Top Guest favourite
A modern kitchen features sleek cabinetry with gold handles, stainless steel appliances, and an ample countertop. A window allows natural light, while a coffee maker and a microwave are visible on the counter. The space is designed for functionality and ease of use.
Cottage in Teaticket
5 out of 5 average rating, 37 reviews

Family Cottage by the Bay

NEW: BIKES FOR FAMILY! Relax in our fully renovated family cottage, steps from a semi-private saltwater beach at Great Pond. Located in the highly sought-after Maravista section of Teaticket, just a mile to Bristol and Heights beaches. Features include a Queen bed in the primary bedroom, bunk beds in the 2nd and 3rd bedrooms, ultra-efficient AC, Level 2 EV CHARGER 6 new BIKES with locks, 55" tv, fully equipped kitchen, 2-person hammock, GRILL, 6 beach chairs, beach cooler and a beach tent.

Top Guest favourite
A comfortable seating area is positioned on a wooden deck, overlooking the calm waterfront. Two cushioned chairs surround a small table, with the harbor and boats visible in the background as the soft hues of twilight reflect on the water.
Cottage in Tisbury
4.99 out of 5 average rating, 68 reviews

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!

Top Guest favourite
A wooden staircase leads down through lush greenery towards a serene lake. Vibrant flowers in a planter add a touch of color to the natural landscape, while tall trees frame the scene, creating a peaceful atmosphere.
Apartment in Sandwich
4.92 out of 5 average rating, 136 reviews

Spacious 2 Bedroom Lakefront Suite

This beautifully furnished, waterfront, 2 bedroom suite is perfect for people seeking to unwind at a Cape Cod getaway, close to Cape Cod canal and boardwalk and within the historic township of Sandwich, with ocean beaches near by. It has a wrap-around deck overseeing the lake, with access from every room on the lower deck and separate entrance. Each room has spectacular views of the lake and evening sunsets. Our private beach is a few steps away and is available for your enjoyment.

Top Guest favourite
A light blue condominium building stands prominently along a paved road leading to the shoreline. The ocean is visible in the background, with a sandy beach accessible via a pathway. A clear blue sky enhances the serene coastal atmosphere.
Condo in Oak Bluffs
4.97 out of 5 average rating, 33 reviews

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Enjoy one of THE most desirable locations on the Vineyard! Enjoy AMAZING sunrises & SPECTACULAR ocean views from this family-run, premier top floor condo. Across street from popular town beach, short walk to Ocean Park, Waban Park, Flying Horses, Steamship Authority & downtown Circuit Ave (restaurants, shops). Bring a car (one unreserved parking spot available) or walk over from boat. Bike delivery & storage available. Linens, beach towels & chairs provided. Island Paradise! ☀️🏖️

Top Guest favourite
A cozy living area features a lightweight sofa adorned with colorful cushions, complemented by a pink upholstered chair. Large windows reveal ocean views, allowing natural light to fill the space. A small table holds fruit and a book, creating a welcoming setting.
Cottage in Chappaquiddick
5 out of 5 average rating, 23 reviews

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!

Top Guest favourite
A charming two-story home is framed by vibrant greenery and colorful shrubs, with a paved pathway leading to the entrance. Solar panels adorn the roof, reflecting a commitment to sustainability. Lush grass and well-maintained landscaping create an inviting atmosphere.
Home in Falmouth
5 out of 5 average rating, 160 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.

Top Guest favourite
Condo in New Seabury
4.97 out of 5 average rating, 168 reviews

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).

Guest favourite
A serene living area is depicted, featuring a spacious light-colored sofa and two blue armchairs. A round metallic coffee table sits at the center, complemented by warm lighting from two floor lamps. The natural wood walls and floors add a touch of inviting charm.
Cottage in New Seabury
5 out of 5 average rating, 36 reviews

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!

Popular amenities for Oak Bluffs beachfront rentals

Quick stats about beachfront rentals in Oak Bluffs

  • Total holiday rentals

    Explore 20 holiday rentals in Oak Bluffs

  • Nightly prices starting at

    Oak Bluffs holiday rentals start at $348 AUD per night before taxes and fees

  • Verified guest reviews

    Over 750 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Oak Bluffs holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oak Bluffs rentals

  • 4.9 Average rating

    Oak Bluffs stays are highly rated by guests—averaging 4.9 out of 5!

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