Vacation Rentals & Apartments in Oak Bluffs

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Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$316

COZY,CUTE COTTAGE NEAR TOWN & BEACH.

Oak Bluffs house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$193

Oak Bluffs Contemporary Summer Home

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 1 minutes

Price per night from

$328

Lovely Oak Bluffs home one mile from town and beach

Oak Bluffs house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$529

Luxury Oak Bluffs Home with 18 X 30' Pool

Oak Bluffs house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,143

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$1,376

“Gingerbread House”, water views, large porch!

Oak Bluffs cottage

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$688

Beautiful Oak Bluffs Home with Wonderful Waterviews

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$2,126

Cape Style Home near Lagoon Pond- short walk to Lagoon Beach

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$427

CLASSIC, VINTAGE,GINGERBREAD

Oak Bluffs house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$1,071

OAK BLUFFS VICTORIAN ONE BLOCK FROM BEACH, TWO BLOCKS FROM TOWN!

Oak Bluffs house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 11

Price per night from

$600

Wonderful Contempory Home in Meadow View Farms

Oak Bluffs house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$500

Enjoy Sea Breezes from third floor roof deck!

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$904

Oak Bluffs Cape Not too Far from Town

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$229

Cute Guest House Overlooking the Lagoon

Oak Bluffs house

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$857

Seaglass Cottage on East Chop

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$571

Newly Renovated 2 Bedroom Oak Bluffs House within Walking Distance to Town

Oak Bluffs house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$314

Gracious five bedroom in-town Oak Bluffs victorian

Oak Bluffs house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$500

Clean, comfortable ranch with lots of amenities

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$544

Spectacular Martha's Vineyard Island Home!

Oak Bluffs townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$453

Charming 4 bedroom home in the east chop neighborhood of Oak Bluffs

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$573

Beautiful Four Bedroom Home Walking Distance to Downtown Oak Bluffs

Oak Bluffs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$575

Beautiful Main & Guest house short walk to Lagoon Pond

Oak Bluffs house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$571

Adorable Oak Bluffs Cottage Walking Distance to Town

Oak Bluffs house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$414

ENJOY WATERVIEWS OF SENGENKONTACKET POND FROM THE WONDERFUL DECK

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$279

Completely Renovated Cottage Close to Town

Oak Bluffs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$643

Beautiful Oak Bluffs home on Lagoon Pond with Pool!

Oak Bluffs house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$571

Ocean Park Victorian Carousel House

Oak Bluffs house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$1,475

Four bedroom Oak Bluffs Home

Oak Bluffs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$357

Charming East Chop Home

Oak Bluffs house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$357

Beautiful Four Bedroom Home with Central Air Conditioning

Oak Bluffs house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$446

COME EXPERIENCE THE MAGIC OF THE VINEYARD

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$471

Walk to Oak Bluffs Lagoon

Oak Bluffs house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$600

Beautiful four bedroom home in-town Oak Bluffs

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$429

In-town Oak Bluffs House

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$286

CLASSIC AND CHARMING COTTAGE WALKING DISTANCE TO THE BEACH AND TOWN

Oak Bluffs house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

“Family Fun” The house was comfortable and clean. It was family vacation that will remain memorable. With the exception of the rainy weather on several days. The house contributed to a lovely stay

Price per night from

$300

Charming Oak Bluffs Cottage within Walking Distance to Town

Oak Bluffs house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$714

Great Four Bedroom Home in Meadow View Farms

Oak Bluffs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$457

Viewing 38 of 441
rentals in Oak Bluffs

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About Oak Bluffs

The town of Oak Bluffs lies on the island of Martha’s Vineyard and is a popular tourist destination during the summer months, home to the largest marina on the island. Choose from over 900 Oak Bluffs vacation rentals and find your dream accommodation with FlipKey.

About Oak Bluffs

The pretty Gingerbread Cottages here have appealed to vacationers for over 100 years, and it’s easy to see why this quaint and charming town remains such a popular destination. With ferries arriving at the harbor from the mainland several times a day, families and couples come to Oak Bluffs for a relaxing break.

Beautiful beaches, rich history to explore and plenty of outdoor activities like golfing, fishing and hiking ensure that Oak Bluffs has everything you need for a great vacation. While you’re here, dine on delights such as fried seafood, blackened catfish and jambalaya. Wash it all down with a beer or root beer from the Offshore Ale Company, the island’s only brewery.

With around 203 sunny days a year, summer is definitely the warmest time to visit the town, but Oak Bluffs is just as beautiful during the Fall. Average summer temperatures are around 78 degrees Fahrenheit.

What to do

The beaches here are simply stunning, whether you head for Oak Bluffs Town Beach or relax on Joseph A. Sylvia State Beach. With two miles of golden sands, the calm waters and views of Cape Cod ensure this is a popular family spot that’s also good for windsurfing.

The marina here is a great spot for drinks and dining, with events like the Harbor Festival held here during the summer months. You’ll find the majority of stores, bars and restaurants on Circuit Avenue.

Don’t miss the chance to see the Flying Horses Carousel, the oldest operating carousel in the US, with hand-carved horses created in 1876.

There are plenty of outdoor activities here, too, with family fishing expeditions leaving from Oak Bluffs Dock and Farm Neck Golf Course with its 18-hole championship course and driving range. Pecoy Point Preserve is also nearby, with 14 acres of trails.

Top Oak Bluffs travel tips

Ferries arrive at the harbor from the mainland from five different destinations in Massachusetts: Falmouth, North Kingstown, Woods Hole, New Bedford and Hyannis.

The best way to explore this compact town is definitely on foot, but there is a bus service, or you can rent a bike or moped in the town center. There’s also a free pedicab service, with any tips and donations going to charity.

Beautiful beaches, family-friendly restaurants and outdoor activities continue to draw visitors to Oak Bluffs year after year.

Why not book a vacation rental with ocean views on FlipKey today and come find out what Oak Bluffs has to offer?

Top Destination reviews

Oak Bluffs Contemporary Summer Home
Great location

The location is great especially if you have teenagers. They can make their way to town with or without you. The layout is a little quirky but overall nice. The house overall was true to the posting. Cons: there wasn't any storage for non-perishable food in the kitchen. The posting should include bringing your own sheets and towels. Use of the washer and dryer would be nice and the downstairs area had moisture issues. Overall I would recommend the house to friends. … see more
CLASSIC AND CHARMING COTTAGE WALKING DISTANCE TO THE BEACH AND TOWN
Great!

The home was large enough to accommodate everyone. Our family had a fantastic time! … see more
Adorable GINGER BREAD house on MV..NICE !!!
Wonderful cottage

We have just returned from a wonderful week at Tranquility Cottage. Our stay was perfect. The cottage contained everything we needed. The downstairs was much more spacious than it appeared in the photos. Location could not have been better. Located in the peaceful surrounds of the Campground, yet within close walking distance of the harbor, Circuit Avenue and Ocean Park. The owner, Mike Mitchell, was very accommodating prior to our trip with very useful info about the cottage. He was a pleasure to deal with. I would highly recommend this cottage to my friends and family. … see more
Lovely Oak Bluffs home one mile from town and beach
we had a blast

the house was nice we loved it, it could use a little tlc but even as is I would recommend this place, nice quiet street close to everything,also the amenities were fablous … see more
COME EXPERIENCE THE MAGIC OF THE VINEYARD
Great Time!

The house and furnishings were very nice. The beds were a little hard, which could easily be fixed by an egg-carton type pad. The utensils in the kitchen were not good for cooking, they melted every time they touched the pan. The grill could use a major cleaning, and also having a grill brush handy would be ideal. For some reason while we were there, the queen size bedroom's electric didn't work, but it was not a big deal for us, because we didn't use that room at all. There's a fire pit, but we had no idea where to get firewood to build a fire. Flyers or phone numbers would have helped. Also we were 'supposed' to have bicycles with the rental, and we couldn't find them. I emailed the owners, and he called me right away saying it was a liability to have bikes with the property. Very understandable. That's the reason we chose this house, because it had so many of the things we needed/wanted. But we rented bikes for two days and the owners reimbursed us, because it was advertised as having bicycles with the property. There was a pack-n-play and a high chair and booster seat. That's very helpful with an 11 month old little girl. Overall it was a great experience and we would definitely stay here again if we vacation on the Vineyard in the future! … see more
OAK BLUFFS VICTORIAN ONE BLOCK FROM BEACH, TWO BLOCKS FROM TOWN!
We had a restful time and we laughed alot - the porch was great!

The house was very nice - we had fun laughing and playing games. Proximity to the beach and town was great and all within walking distance. The layout was nice except the difficult steep stairs near kitchen - overall great time. … see more

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