Discover a selection of 48 vacation rentals in Oak Bluffs, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $430 per night, and houses and condos are popular options for a stay in Oak Bluffs. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Oak Bluffs
Destination guide

Take the ferry to fun at Oak Bluffs

If you're heading over to Martha's Vineyard, the chances are Oak Bluffs is where you'll step off the ferry. And there's probably no need to go further. Oak Bluffs—with its placid beaches, its ice cream parlors piled with fancies, and its streets lined with gingerbread cottages—has plenty to delight visitors. There are also carousels to ride, fishing boats to hire, and winding lanes to bike down. No wonder that Oak Bluffs vacation rentals top the list for places to stay on MV, especially for those with kids.

Things to do

Sightseeing in and around Oak Bluffs

Are you looking for top things to see and do in the city? Venture out of your cozy vacation rental and experience everything that makes Oak Bluffs a fun place to get away. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Farm Neck Golf Club (1.2 mi / 2 km)
  • Shining Sea Bikeway (9.2 mi / 14.8 km)
  • Cape Cod Country Club (11.5 mi / 18.5 km)
  • Falmouth Country Club (10 mi / 16.1 km)
  • Mashpee River Reservation (13.2 mi / 21.2 km)
  • Stand Up & Paddle Cape Cod (15.1 mi / 24.3 km)

Oak Bluffs—simple seaside pleasures

As a town surrounded on three sides by the sea, much of what goes on in Oak Bluffs involves a healthy mix of sun, sea, and sand. Picnic hampers and spades at the ready, then, for days of paddling, sunbathing, and snacking next to sun-spangled waves. The more active-minded can grab a paddle, and head out in a kayak or on a paddleboard since the waters are calm here. Then there are lungfuls of fresh, salt-tanged air to invigorate those taking fishing trips around the area. And greens with a view greet those teeing up at Oak Bluffs' scenic golf course.


Oak Bluffs—a walk on the mild side

The Atlantic Ocean plays a big role in Martha's Vineyard weather, helping to keep this Massachusetts island relatively mild, whatever the season. If you've booked Oak Bluffs vacation rentals to make the most of the beach, July or August are ideal: expect a warm 70-80°F with few rainy days. September is only slightly cooler, a rather pleasant 70°F, and you'll notice the streets and ice-cream parlors are a little less crowded. And while spring may be fresh, it is the perfect time enjoy an outdoors Oak Bluffs break, glowing at its verdant best.

Natural features

The bays and birds of Oak Bluffs

It's out in the bays surrounding Martha's Vineyard that nature is at its wildest. Boats can be hired to whisk you out to spot whales or dolphins. On land, Oak Bluffs presents its softer side, with its gently rolling fields, woods, and meadows. These slip into marshes or dune banks where they meet the sea. There are some wonderful birding chances at nature preserves like Felix Neck Wildlife Sanctuary, with swans, kestrels, and heron being common. And by the shore, you may find crabs, clams, shrimp, or even the primal and bizarre horseshoe crabs.

How to get there

Transportation to and around Oak Bluffs

The nearest airport is in Vineyard Haven, MA (MVY-Martha's Vineyard), located 5.2 mi (8.3 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Hyannis, MA (HYA-Barnstable Municipal), which is 20.5 mi (32.9 km) away.

What are the top vacation rentals in or near Oak Bluffs?

Whether you're in search of an intimate escape for you and your sweetie or someplace roomy to fit family and friends, you'll find some top vacation rentals in and around Oak Bluffs. Here are a couple to get you inspired:

  • Around 11 miles from the center of Oak Bluffs, it's hard to beat "Exceptional - Waterfront Home". It has 3 bedrooms and handy features including golf and an iron and ironing board.
  • Alternatively, make a booking at "Panoramic Views Of Snug Harbor In Beautiful West Falmouth". Located around 12 miles from the heart of Oak Bluffs, it has 6 bedrooms and features WiFi and high-speed internet services.

For even more great options, use the search bar at the top of the page to find the perfect Oak Bluffs vacation rental for you.

What are the best tiny house vacation rentals in or near Oak Bluffs?

Punching way above its weight when it comes to character and ingenuity, a tiny house vacation rental in Oak Bluffs delivers big adventure. Disconnect all your gadgets and turn your focus to outdoor fun at one of these compact stays:

  • Take a few days off to experience a simpler way of life at "Marion Village's Very Best Cottage - Tiny Home Living Close To The Town Beach". Located in Marion Center, a dryer and a microwave oven are included here.
  • "Stay In A Tiny House 0. 4mi To Beach Village Restaurants Pet Friendly 2 Bikes" offers plenty of conveniences, including a toaster and a boat. Located in Dennis Port, you'll be able to live large in this small but cleverly designed abode.

Can I find log cabins to rent in or near Oak Bluffs?

Choose a charming log cabin from the many dotted in or around Oak Bluffs and you'll soon be inside your wooden hideaway, wine in hand, unwinding next to a blazing fire. But adventure is right outside your door too. These cabins promise the perfect blend of comfort and fun:

  • "Spacious Wellfleet Tree Top Log Cabin Great For Families And Reunions": Enjoy a few days relaxing at this great escape surrounded by nature. Once you've recharged, enjoy golf or windsurfing, which are among the fun things to do in this region.
  • "Rustic Cozy Log Cabin": After a big day of trying out some popular local pastimes, such as mountain biking and cross-country skiing, recharge your batteries at this top-rated property.

What are the top-rated vacation rentals for weekend getaways in or near Oak Bluffs?

Nothing tops a short escape to perk you up. Pack your carry-on bag and catch your breath at one of these enticing weekend getaways in and around Oak Bluffs:

  • Enjoy a change of scenery at "Luxurious Estate Includes - Tennis Court", which is around 20 miles to the northeast of Oak Bluffs. There's plenty of nature and adventure to keep you happy here. Try surfing and boogie boarding and basketball or simply delight in the sights of Veterans Memorial Park and Long Beach.
  • "Oceanfront Contemporary Home - Breathtaking Views" is another great setting for a fun few days away. Around 20 miles north of Oak Bluffs, use it as a base to try some mountain biking or sailing. John Jenney Museum and Woods Hole Historical Museum also have to be on your to-do list while you're here.

Can I find studio apartments for rent in and around Oak Bluffs?

Usually compact, reasonably priced and well located, it's hard not to be impressed by a studio apartment. Settle into one of these vacation rentals and get to know Oak Bluffs up close:

  • Make "Luxurious Harbor View “eliza” Cottage Next To White Elephant" your home for a few days or more. This sought-after vacation rental features amenities including a nearby waterfront and a hair dryer.
  • Alternatively, get away to "Cape Cod/oceanfront On Nantucket Sound W", which offers conveniences including cable/satellite TV services and a nearby beach.

With the cash you save on your studio apartment, you can afford to explore even more of Oak Bluffs. Cultural sights like Isabella Stewart Gardner Museum and Roxbury Center for Arts will help you better understand the personality of this destination.

Can I find short term rentals in or near Oak Bluffs?

Every once in a while, you just need to take a break from the real world, even if it's only for a couple of days. Enjoy a delightful mix of exploring and relaxing at one of these short-term rentals in or around Oak Bluffs:

  • Close to the center of Oak Bluffs, "Located Steps Away To Main Street And. 7 Miles From Surf Drive Beach" is the perfect place for a short and sweet break. While you're about, be sure to visit well-known attractions like Walden Pond and Louisa May Alcott's Orchard House.
  • Eat, sleep and explore what's around you from "Water View - Walk Town/beach, Pets Considered", another terrific option. Old Manse and Concord Visitors Center should be on your must-do list when you're ready to see the sights.

What are the best romantic weekend getaways in or near Oak Bluffs?

Whether spent in a log cabin or a beach house, a romantic weekend getaway is a wonderful way to add some fire to your relationship. Whisk your honey off for a couple of leisurely days at one of these escapes in or near Oak Bluffs:

  • Around 11 miles from Oak Bluffs, "Exceptional - Waterfront Home" is the perfect place for doting couples. Beauty services and a resort are some of the many amenities you'll find here.
  • Another place where you can enjoy a few idyllic days together is "Panoramic Views Of Snug Harbor In Beautiful West Falmouth". Around 12 miles from Oak Bluffs, a fireplace and a nearby bay add to the ambiance here.

What are the best large group vacation rentals in or near Oak Bluffs?

Big groups mean big-time fun. They also mean finding a place that'll effortlessly fit your whole gang. Check out our large group vacation rentals in or around Oak Bluffs and get everybody together under one roof:

  • You'll have plenty of space to enjoy yourselves at "Panoramic Views Of Snug Harbor In Beautiful West Falmouth". Around 12 miles north of Oak Bluffs, this impressive property has 6 bedrooms and sleeps up to 12 guests. Top amenities include a water park and a kitchen.
  • "Luxurious Estate Includes - Tennis Court" is another excellent option. It's around 20 miles to the northeast of Oak Bluffs, has 6 bedrooms and accommodates up to 14 guests. A swimming pool and a kitchen are just a couple of things designed to make your stay even more comfortable.

What are the best houses for rent with a pool in or near Oak Bluffs?

Of all the conveniences a vacation rental can have, a pool delivers the most fun. Take a peek at these houses for rent with a pool in or near Oak Bluffs and spend your days splashing around. Just don't forget your inflatable pizza slice:

  • Pack your swimsuit and get away with your gang to "New House, Steps To Beaches, Main St". There are also lots of other convenient amenities here, including pet-friendly facilities and a toaster.
  • "Hóll Adventure House - Perfect For Groups" is the type of place you go to leave the everyday behind and appreciate your surroundings, starting with its pool. A dishwasher and a meal delivery service are also on hand to make your stay nice and comfortable.

Not sure what the weather is like in Oak Bluffs? It has a humid subtropical climate, with average summertime temperatures ranging from 65 ºF to 70 ºF. If you'd like more inspiration on where to stay in this epic destination, use the search bar at the top of the page and adjust the filters to look through our entire range of Oak Bluffs vacation rentals.

What are the best large family vacation rentals in or near Oak Bluffs?

It's always more fun to share precious moments with the people closest to your heart. Whether you're organizing a family get-together or taking time out with good friends, we'll have a large vacation rental that's perfect for you. These are two of our best in and around Oak Bluffs:

  • About 12 miles to the north of Oak Bluffs, "Panoramic Views Of Snug Harbor In Beautiful West Falmouth" has 6 bedrooms and sleeps up to 12 guests. It comes with lots of amenities, including childrens activities and a kitchen.
  • "Luxurious Estate Includes - Tennis Court" also has the space you need to connect with loved ones. This rental is around 20 miles to the northeast of Oak Bluffs, and accommodates 14 guests in its 6 bedrooms. A stereo and childrens activities will help keep everyone happy and comfortable.

When it's time to leave the house and explore, there are loads of family-friendly attractions nearby to keep everyone happy and entertained. New England Aquarium, Newbury Street and CoCo Key Water Resort - Boston should be at the top of your to-do list.