Beachfront holiday rental in Oak Bluffs

Find and book unique beachfront homes on Airbnb

Top-rated beachfront accommodation in Oak Bluffs

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Edgartown

4.83 out of 5 average rating, 70 reviews

Spacious, Old Vineyard charm with Private Beach

This is a classic, rare vintage Vineyard property: a beautifully simple, comfortable, and charming family house located directly on its own private beach on Katama Bay. Peaceful and secluded, yet a short walk or bike ride to the popular, public surf beach, and 3 miles from bustling, historic Edgartown. The house is both intimate and expansive: equally perfect for small families or larger groups, for quiet retreats or festive reunions. Spacious and soulful indoors and out. A magical refuge. .

Superhost

Cabin in Mattapoisett

4.92 out of 5 average rating, 24 reviews

Beach Escape

Private, sandy beach across the street on warm, calm Buzzards Bay. Spectacular sunsets over back marsh/pond. This newly renovated rustic, sunny, summer cottage is a studio for two adults. It offers pull out king sofa with two comfortable lounging chairs. Two unit electric stovetop, Keurig, propane grill, enclosed outdoor shower only. No children/pets/SMOKERS. Please bring your own toiletries, sheets,towels. Biking, walking trails nearby. No Cape Cod bridges or traffic. A piece of heaven.

Top Guest favourite

Home in Mashpee

5 out of 5 average rating, 10 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.

Top Guest favourite

Condo in Oak Bluffs

5 out of 5 average rating, 27 reviews

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!

Top Guest favourite

Apartment in Tisbury

4.92 out of 5 average rating, 131 reviews

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.

Top Guest favourite

Cottage in Mattapoisett

4.92 out of 5 average rating, 38 reviews

Cozy Mattapoisett Cottage Footsteps to the Beach

This Charming Cozy Cottage is situated on well maintained grounds that offer ocean views from the front deck & garden. Tastefully decorated & fully equipped. Only a 1-2 minute walk grants access to the neighborhood private beach. The area is peaceful & secluded. Once you get your groceries you will never want to leave. Mornings, you will be serenaded by the beautiful sounds of nature. Enjoy the magnificent ever changing scenarios of gorgeous sunrises & sunsets over Nasketucket Bay.

Guest favourite

Cottage in New Seabury

4.91 out of 5 average rating, 170 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 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 w/ 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!

Top Guest favourite

Bungalow in Cotuit

4.98 out of 5 average rating, 59 reviews

Cozy Cape Cod Beach House Bungalow

Anyone who books this house will absolutely fall in love with it and the town of Cotuit! The beach house is on a private beach and is part of a larger family estate that has been in the family for four generations. The one-bedroom/two-bath rustic beach house is surrounded by nature. It provides enough space for solo travelers or couples looking for a romantic spot or a no-frills writer’s retreat. It's given our family such amazing memories and we're excited to share it with you!

Top Guest favourite

Home in Falmouth

5 out of 5 average rating, 154 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 favourite

Cottage in New Seabury

5 out of 5 average rating, 29 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!

Guest favourite

Home in Chilmark

4.87 out of 5 average rating, 55 reviews

Cozy Waterfront Cottage, Newly Remodeled!

Beautifully upgraded WATERFRONT cottage in Menemsha with (essentially a) PRIVATE BEACH! Direct access to Vineyard Sound from your own staircase leading down to the water’s edge. Enjoy stunning sunsets and breathtaking views from every room. Private and peaceful but conveniently located just a short drive or bike ride to Menemsha or the Chilmark village center.

Guest favourite

Home in Mashpee

4.96 out of 5 average rating, 190 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!