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Beachfront vacation rentals in Oak Bluffs

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Quick stats about beachfront rentals in Oak Bluffs

  • Total vacation rentals

    Explore 30 vacation rentals in Oak Bluffs

  • Nightly prices starting at

    Oak Bluffs vacation rentals start at €164 per night before taxes and fees

  • Verified guest reviews

    Over 1,140 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Oak Bluffs vacation 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!

Top-rated beachfront rentals in Oak Bluffs

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

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Guest favorite
A round black table is positioned between two comfortable chairs adorned with patterned upholstery. Atop the table, a decorative floral arrangement includes blue and white flowers, complemented by greenery. A couple of neatly stacked books are also visible.
Condo in Oak Bluffs

Serenity on Martha's Vineyard

This 2BR, 2 Full Bath Condo with air condition (AC) and elevator access is located across the street from State Beach (AKA the "Ink Well") in Oak Bluffs. It's on the top floor, recently redecorated, with all the amenities for a wonderful vacation. Both bedrooms have Smart TVs & AC. Free Wi-Fi. Great location, within walking distance to the ferry, beach and downtown Oak Bluffs, restaurants and shops. Car not needed! Get ready to relax and unwind. It's the perfect location! Welcome to Serenity!

4.82 out of 5 average rating, 56 reviews
Top guest favorite
A kitchen area features a bar with three wooden stools, inviting casual dining. Hanging pots and pans are showcased above the counter, while a vase of red roses adds a touch of color. A brick wall complements the white cabinetry and appliances.
Apartment in Tisbury

Harbor view apartment, a quick walk from the ferry

This is a great one bedroom apartment on the second floor of a house. My place is close to the beach, public transport, the Steamship Authority ferry, Black Dog Tavern, Main Street Vineyard Haven, Stop & Shop grocery, and lots of great shopping. You’ll love the convenience! Walk to the apartment right off the ferry boat. Lots to do in walking distance, and onsite parking. The Martha's Vineyard Museum is a 5 minute walk, down the same street. My place is great for couples and solo adventurers.

4.93 out of 5 average rating, 150 reviews
Top guest favorite
A serene view of the ocean is framed by white wooden architecture. The calm water reflects a clear blue sky, while a sandy beach lies in the foreground, accompanied by a stone jetty. Benches are positioned along the walkway, inviting relaxation.
Condo in Oak Bluffs

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!

5.0 out of 5 average rating, 34 reviews
Guest favorite
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

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!

4.9 out of 5 average rating, 196 reviews
Top guest favorite
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

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.

4.92 out of 5 average rating, 145 reviews
Guest favorite
Home in Tisbury

Vineyard Haven Home | 5 min to beach | 5 beds

Perfect home for one or two families looking for a summer vacation on MV. Four bedrooms and a daybed, 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. House comfortably fits 8 with room for a 9th on a daybed.

4.92 out of 5 average rating, 26 reviews
Top guest favorite
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

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!

5.0 out of 5 average rating, 35 reviews
Top guest favorite
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

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.

5.0 out of 5 average rating, 170 reviews
Guest favorite
The exterior of the house is surrounded by lush greenery, featuring a spacious yard with a picnic table and a stone wall. A guest cottage is visible, alongside a deck with outdoor seating and an umbrella. Tall trees provide shade on a sunny day.
Home in Oak Bluffs

First-class 4+ BR Lagoon Pond Camp

Ultimate getaway house! Situated on Lagoon Pond in Oak Bluffs. Sleeps 10 plus 2 in the optional guest cottage. The house is under 2 miles from OB center - convenient for walking and bike riding. Beach access! The house boasts a pizza oven, outdoor nooks (hammocks!), and a spacious yard. There are amenities galore including, but not limited to: an outdoor shower, grill, board games, wifi, towels, linens, etc. 1 week min stay, Sunday turnovers in July & August.

4.94 out of 5 average rating, 67 reviews
Top guest favorite
A vibrant green kayak glides over calm waters, with a person seated inside holding a paddle. In the background, a cottage displays large wall-to-wall windows reflecting the surrounding trees, providing a connection to nature.
Home in Sandwich

WOW LAKE VIEW! Waterfront with Beach, King Bed

Wake up to magnificent Panoramic Views of a Beautiful Lake with Waves Lapping below your Window! Scan the QR code to See a Full Video Tour on YouTube. Guests love its Stylish, Peaceful, Open Design; Wall-to-Wall, Floor-to-Ceiling Windows; Private Beach with Chaise Lounge Chairs; a Full, Modern Kitchen; Comfortable King hybrid gel/coil Bed; Private Office; Bathroom with Curved Shower; AC, and Much More! It's like being on your own Luxury Houseboat!

4.96 out of 5 average rating, 280 reviews
Guest favorite
Condo in New Seabury

New Seabury Cape Condo | Pool & Beach Escape

Top 5% of Air Bnbs! Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.

4.97 out of 5 average rating, 179 reviews
Superhost
A cozy living area showcases a large, comfortable sofa and a wooden coffee table, with a mounted map adding character to the space. Sunlight streams through multiple windows, illuminating the room's airy feel. A dining table is visible, suggesting a welcoming atmosphere for gatherings.
Home in Chilmark

Evelyn's Menemsha Camp - Best Vineyard View

Evelyn's House on the hill overlooking Menemsha Beach is the classic Marthas Vineyard Beach Cottage. Evelyn Flanders built her " Camp"in 1909 where the views of Menemsha Harbor and famous sunsets would be about as good as it gets. It's the same today. With 2 bedrooms, 2 baths and a loft it's perfect beach base camp.. Take the path to Menemsha beach or your passes to Lucy Vincent. You are most welcome to bring one pet.

4.85 out of 5 average rating, 20 reviews

Popular amenities for Oak Bluffs beachfront rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly beachfront home rentals

Superhost
A beach cottage showcases a wooden deck leading up to its exterior, featuring multiple windows and a blue trim. Surrounding greenery and sandy terrain create a natural setting. The entrance is visible, alongside a glimpse of parked vehicles in the background.
Cabin in Aquinnah

50s Cottage on Martha’s Vineyard w/Private beach

4.61 out of 5 average rating, 61 reviews
Guest favorite
Cottage in Falmouth

Cheerful 4 bedroom cottage, private beach access

4.94 out of 5 average rating, 17 reviews
Guest favorite
Four kayaks in vibrant colors are positioned on a grassy area by the water's edge. A calm bay reflects the surrounding scenery, and a dock with boats is visible in the background. The tranquil setting emphasizes the peaceful waterfront location.
Home in Mashpee

Waterfront, beach, dock, Kayaks. 8/29 2nt special

4.75 out of 5 average rating, 40 reviews
Guest favorite
The entrance of the Cape Cod home is framed by lush greenery and low maintenance plants. Natural stone pathways lead to the inviting porch, where a welcome sign is displayed. Soft shadows are cast by the surrounding trees, creating a serene, welcoming entryway.
Home in Falmouth

Salt Pond Bird Sanctuary Sunset

4.95 out of 5 average rating, 100 reviews
Top guest favorite
Home in Oak Bluffs

Waterfront, large home and yard

4.94 out of 5 average rating, 48 reviews
Guest favorite
The exterior of a classic Cape home is showcased, featuring shingle siding and white trim. A welcoming entrance is highlighted by a red door and a white porch. Lush greenery surrounds the house, with a pink chair positioned on the porch.
Home in Woods Hole

Woods Hole with views of Great Harbor.

4.95 out of 5 average rating, 21 reviews
Home in Chappaquiddick

Classic Chappy Beach House

5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Mashpee

Beach house on Waquoit Bay

5.0 out of 5 average rating, 8 reviews

Beachfront home rentals with a pool

The entrance of the condominium is shown, featuring a wooden exterior with shingles. A pathway leads to the door, surrounded by neatly trimmed shrubs and grass. Bright sunlight highlights the clear sky and the inviting pathway.
Condo in Falmouth

Condo in Falmouth MA

4.72 out of 5 average rating, 47 reviewsA two-story country home is surrounded by a grassy yard and features a deck made of wooden slats. The exterior showcases a traditional design with wooden shingles and green accents on the doors. A clear blue sky provides a bright backdrop.
Home in West Tisbury

Charming Getaway Post&Beam Home Cozy and Sweet

5.0 out of 5 average rating, 5 reviewsA relaxing outdoor pool area features lounge chairs arranged along the pool's edge. The surrounding building, showcasing spacious balconies, houses multiple units. Guests enjoy sunbathing and walking nearby, with clear skies overhead enhancing the scene.
Condo in Falmouth

Two bedroom condo .on the water Falmouth, ma

5.0 out of 5 average rating, 5 reviews
Superhost
The exterior of a three-story resort building features a stone façade, multiple balconies, and well-maintained landscaping. A brick fence and pathway are visible in front, providing access from the road. The sky appears cloudy, suggesting an overcast atmosphere.
Resort in Falmouth

Captain's Quarters, Cape Cod

5.0 out of 5 average rating, 3 reviews
Hotel room in North Falmouth

Escape to Beachside Bliss | Suite w/ Ocean View

Hotel room in North Falmouth

Serene Beachside Room w/ Stunning Sunset Views

Hotel room in North Falmouth

Breathtaking Old Silver Beach Access, 2 Rooms

Hotel room in North Falmouth

Stunning Cape Rod Getaway w/ Private Beach Access

Private beachfront home rentals

Superhost
A panoramic view showcases a sandy beach meeting calm ocean waters under a clear blue sky. Lush green grass lines a white picket fence, providing a sense of privacy. Small groups of people can be seen enjoying the beach, creating a relaxed coastal scene.
Cottage in New Seabury

Private Beach Cottage steps to private beach

4.87 out of 5 average rating, 60 reviews
Guest favorite
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

Nantucket Style Cottage Steps from Private Beach

4.98 out of 5 average rating, 42 reviews
Top guest favorite
The spacious foyer features a grand staircase leading to the upper level. Expansive windows allow natural light to fill the room, highlighting the polished wooden floors. A cozy seating area is arranged by the windows, complemented by a vibrant area rug and a modern fireplace.
Home in Sandwich

Lakefront Modern Luxury * Private Beach * Cape Cod

5.0 out of 5 average rating, 95 reviews
Top guest favorite
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 Falmouth

Family Cottage by the Bay

5.0 out of 5 average rating, 65 reviews
Top guest favorite
A private deck features a glass-topped table set for dining, surrounded by black metal chairs. Soft blue cushions add comfort to the seating area, while a vase with yellow tulips brings a pop of color. The tranquil view of Deans Pond complements the inviting outdoor space.
Place to stay in New Seabury

Summer at Serenity By The Sea!

4.96 out of 5 average rating, 90 reviews
Top guest favorite
A view from a wooden deck showcases tranquil Jenkins Pond, surrounded by tall trees and clear blue sky. Sunlight reflects off the water's surface, highlighting the serene outdoor setting that invites relaxation.
Home in Falmouth

Stunning 4-bedroom Private Fresh Water Beach Front

4.99 out of 5 average rating, 80 reviews
Superhost
A serene outdoor patio area is presented, featuring a circular table with seating for four beneath a large umbrella. Lush greenery surrounds the space, with a white lattice fence in the background and colorful flowers adding a touch of vibrancy.
Cottage in Mashpee

The Loveshack, Steps to Private Waterfront

4.73 out of 5 average rating, 139 reviews
Guest favorite
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

Comfy beach house in Mattapoisett

4.88 out of 5 average rating, 42 reviews

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