EMAIL: rent@sandpiperrental.com TELEPHONE: 508.627.6070
Need Ferry Tickets? Click Here to Find Out How!

Oak Bluffs Rentals

Our Oak Bluffs rentals are the prime summer vacation destination in Martha's Vineyard. Its fun and active ambiance really opens up with the arrival of Memorial weekend and stays in full swing until Columbus weekend. It has historically been a summer destination dating back to the mid 1800’s when the camp ground cottages were developed as a Methodist summer retreat which actually started with camp sites and developed into the quaint, colorful gingerbread cottages that we see today.

For attractions near your Oak Bluff vacation rentals, visit the town center,  located on the harbor and has a high energy level with hundreds of boats coming and going. Circuit Avenue is the commercial heart of Oak Bluffs. It has ice cream and sunscreen, coffee stands and souvenir shops. It has Reliable Self-Serve Market, family owned and operated, and Giordano's Restaurant and Clam Bar, offering up family style meals since 1930. It has Back Door Doughnuts (on a summer's night, between 9 p.m. and 12:30 a.m., buy them fresh from the oven in the parking lot behind Reliable Market.). Circuit Avenue starts with the Flying Horses Carousel, the nation's oldest operating platform carousel and a National Historical Landmark owned by the Martha's Vineyard Preservation Trust and ends with the start of the Art District on the other end. Oak Bluffs also hosts the "summer” steamship authority terminal adding to its high summer foot traffic.

There are many residential areas outside of the downtown that offer quiet privacy for your summer vacation yet have easy access to downtown Oak Bluffs, Edgartown and Vineyard Haven. Contact us for more information about any of the Oak Bluffs rentals on our site.


You may search for your vacation accommodations here. We have offered you several ways to search and locate your accommodations below.

Refine Your Search

Pick Your Dates

My dates are flexible

Number of Bedrooms

Sleeps

Area

Property Code

Features

Water

94 properties found

8013 Bed / 2.5 Bath / Sleeps 6

Oak Bluffs

More Details
A unique 3 bedroom 2.5 bathroom home built in the round on East Chop Drive overlooking the East Chop Lighthouse. Yes, th...read more

80113 Bed / 1.5 Bath / Sleeps 6

Oak Bluffs

More Details
Sparkling Vineyard cottage has the fresh airy updates with painted white ship lap for wall decor, hardwoods and stainles...read more

80146 Bed / 2.5 Bath / Sleeps 14

Oak Bluffs

More Details
This 6 bedroom Oak Bluffs Gingerbread home is well appointed with a grand open floor plan, chefs kitchen, formal dining,...read more

80164 Bed / 5.5 Bath / Sleeps 8

Oak Bluffs

More Details
A stoic restoration reveals a truly stunning home in Ocean Park - with a gourmet kitchen adorned with antique accents, a...read more

80176 Bed / 6.5 Bath / Sleeps 14

Oak Bluffs

More Details
ONLY A FIVE MINUTE WALK TO OAK BLUFFS CENTER! On the outskirts of the infamous Oak Bluffs ginger bread cottages, this ho...read more

80182 Bed / 2.0 Bath / Sleeps 4

Oak Bluffs

More Details
Modern two bedroom home just steps from everything you want to do in Oak Bluffs. Classic post and beam design packs a lo...read more

80194 Bed / 4.5 Bath / Sleeps 10

Oak Bluffs

More Details
ONLY A FIVE MINUTE WALK TO OAK BLUFFS CENTER! On the outskirts of the infamous Oak Bluffs ginger bread cottages, this ho...read more

8024 Bed / 2.5 Bath / Sleeps 8

Oak Bluffs

More Details
Prime Oak Bluffs location in a serene setting. This family home has plenty of room to spread out and enjoy your vacation...read more

80206 Bed / 5.5 Bath / Sleeps 15

Oak Bluffs

More Details
One of the original Harthaven homes, this freshly renovated is home is still being completed. New bathroom photos to com...read more

80224 Bed / 2.0 Bath / Sleeps 9

Oak Bluffs

More Details
This property offers the ease of getting to and from most sights and activities on the island of Martha's Vineyard. Just...read more