Beachfront holiday rentals in Oak Bluffs

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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 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. .

Top guest favourite

Home in Mashpee

5 out of 5 average rating, 9 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.

Guest favourite

Home in North Falmouth

4.91 out of 5 average rating, 69 reviews

Waterfront Cape Cod Escape w/ Water Access

Create lifelong memories at this exclusive Cape Cod waterfront retreat on a private road! Nestled on an acre with stunning water views, this 4-bedroom home (2 w/ ocean views) boasts a spacious open layout and 2 stylish living rooms. Relax in the large waterfront yard with an inflatable jacuzzi, BBQ, and outdoor shower. Enjoy deep water access, dine under the stars, soak in breathtaking sunsets, visit Old Silver Beach, and explore charming Historic North Falmouth. Your dream Cape Escape awaits!

Guest favourite

Cottage in Sandwich

4.95 out of 5 average rating, 234 reviews

WOW VIEW! Waterfront, Private Beach, King Bed!

Wake up to magnificent panoramic views of a beautiful lake with waves lapping below your window! See a video tour on YouTube: "WOW View! Cape Cod Lakefront Cottage. Private Beach, King bed" Guests love the stylish, peaceful, open design; wall-to-wall, floor-to-ceiling windows; private beach with picnic table and chaise lounge chairs; a full, modern kitchen; luxurious King gel/coil bed, private office, bathroom's curved shower, AC, and much more! It's like being on your own luxury houseboat!

Top guest favourite

Flat in Vineyard Haven

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.

Guest favourite

Apartment in Oak Bluffs

4.97 out of 5 average rating, 30 reviews

LOCATION LOCATION!! Ocean- View TOP Floor Condo

Come stay in one of THE most desirable locations on the Vineyard! Enjoy amazing sunrises & SPECTACULAR ocean views from this family-run, premier top floor (3 of 3) 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 avail. Bed linens & towels are included. We hope to accommodate you!!

Guest favourite

Cottage in New Seabury

4.91 out of 5 average rating, 169 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

Flat in Sandwich

4.92 out of 5 average rating, 132 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

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

Lighthouse in Pocasset

4.94 out of 5 average rating, 110 reviews

Wings Neck Lighthouse

Once in a lifetime experience to stay in a Lighthouse. Historic, unique and charming but with all of the conveniences that make a great vacation. Just feet from the Atlantic with 360 degrees of ocean view. Beautiful, peaceful and memorable all year long. Sandy private association beach just steps away. Expansive lawn and patio for enjoying salt air, waves, boats and sunsets.

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.