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Oak Bluffs Rentals

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Oak Bluffs Rentals

About Oak Bluffs

228 apartments

DOHEM - East Chop Seaside Cottage, Large Porch, WiFi, Spectacular Views

Oak Bluffs house

3 bedrooms / 1 bathroom / Sleeps 6

$529

1 / 13

In-Town Historic Property on Martha's Vineyard

Oak Bluffs apartment

2 bedrooms / 1 bathroom / Sleeps 5

“One of Oak Bluffs best kept secrets!” My family and I have been vineyarders for decades, and have been accustomed to rental property's away from the busy streets of downtown Oak Bluffs. Needless, to say we weren't optomistic about what to expect. Howe

$144

1 / 20

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

3 bedrooms / 2 bathrooms / Sleeps 6

$206

1 / 22

Charming Farmhouse

Oak Bluffs house

4 bedrooms / 1 bathroom / Sleeps 8

$397

1 / 17

ALLER - Oak Bluffs 4 Bedroom Home, Walk to Town and Beach!

Oak Bluffs house

4 bedrooms / 2 bathrooms / Sleeps 8

$386

1 / 17

Cozy condo with shared pool & tennis courts, close to golfing & the beach!

Oak Bluffs house

1 bedroom / 2 bathrooms / Sleeps 6

$108

1 / 24

Charming cottage with deck and playroom one mile from beach

Oak Bluffs house

4 bedrooms / 2 bathrooms / Sleeps 8

$114

1 / 24

BURBR - Perfect Retreat for Large Families, Newly updated, 1.5 miles to Town an

Oak Bluffs house

6 bedrooms / 3 bathrooms / Sleeps 13

$354

1 / 22

PETEV - Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association T

Oak Bluffs house

4 bedrooms / 2 bathrooms / Sleeps 8

$351

1 / 24

HODGO - ADORABLE, RECENTLY RENOVATED COTTAGE, WALK TO TOWN, BEACH and FERRY

Oak Bluffs house

2 bedrooms / 1 bathroom / Sleeps 4

$193

1 / 11

Summer Vacation Rental

Oak Bluffs house

3 bedrooms / 2 bathrooms / Sleeps 8

$300

1 / 11

WHARG - Beautifully Decorated, Private Tennis Court, Walk to Town Center and Ink

Oak Bluffs house

3 bedrooms / 3 bathrooms / Sleeps 6

$557

1 / 23

PATTP - Adorable Pristine Cape, Close to Town Center and Ink Well Beach. Landsca

Oak Bluffs house

3 bedrooms / 2 bathrooms / Sleeps 6

$221

1 / 11

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

$200

1 / 14

SAMAJ - Gorgeous Ocean View Cottage Home, Ink Well Beach Across Street, Walk to

Oak Bluffs house

6 bedrooms / 3 bathrooms / Sleeps 10

$571

1 / 27

KLEIB - Lagoon Waterfront and Beachfront, Spectacular Waterviews, Room A/C, WI

Oak Bluffs house

2 bedrooms / 1 bathroom / Sleeps 4

$221

1 / 20

GIORP - Cute and Cozy Oak Bluffs Cottage, Spacious Deck, Just over a Mile to Oa

Oak Bluffs house

2 bedrooms / 1 bathroom / Sleeps 5

$193

1 / 13

A deck, an enclosed yard - walking distance to the beach, ferry & town!

Oak Bluffs house

5 bedrooms / 2 bathrooms / Sleeps 10

$280

1 / 29

GOLDF - Outstanding Summer Home with Pool, Screened Porch, and Patio Area, Assoc

Oak Bluffs house

5 bedrooms / 2 bathrooms / Sleeps 8

$571

1 / 33

FISHJ - Stylish Contemporary Vacation Home situated in Meadow View Farms, Open L

Oak Bluffs house

4 bedrooms / 4 bathrooms / Sleeps 8

$357

1 / 28

BEAUTIFUL SECLUDED ESCAPE WITH CENTRAL A/C

Oak Bluffs house

4 bedrooms / 4 bathrooms / Sleeps 8

$625

1 / 10

TOTHG - Adorable Updated Vineyard Cottage, Lovely Landscaped Yard, Central A/C,

Oak Bluffs house

3 bedrooms / 1 bathroom / Sleeps 5

$257

1 / 13

Inviting cottage, water access nearby, spacious porch for entertaining!

Oak Bluffs house

2 bedrooms / 2 bathrooms / Sleeps 4

Responds fast! avg. 20 minutes

$177

1 / 27

BRIGY - Outstanding Designer Luxury Home, 18 X 30' Pool, Expansive Bluestone P

Oak Bluffs house

4 bedrooms / 4 bathrooms / Sleeps 8

$1,143

1 / 38

ROCHA - Bridle Path House, Quiet Lovely Neighbohood, Porch and Deck Areas, Lar

Oak Bluffs house

3 bedrooms / 3 bathrooms / Sleeps 8

$286

1 / 21

HAYEL - Gingerbread Cottage, Walk to Town, Harbor Area and Inkwell Beach, Large

Oak Bluffs house

4 bedrooms / 2 bathrooms / Sleeps 7

$529

1 / 12

ARMSA - Cozy Newly updated Seashore Cottage, East Chop Highlands Area, Farmers

Oak Bluffs house

3 bedrooms / 2 bathrooms / Sleeps 6

$286

1 / 29

TRAVM - Updated East Chop Area Summer Retreat, Great Proximity to Town Center a

Oak Bluffs house

4 bedrooms / 2 bathrooms / Sleeps 8

$400

1 / 27

CENCR - Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Grea

Oak Bluffs house

4 bedrooms / 3 bathrooms / Sleeps 8

$429

1 / 27

VANAL - Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Bea

Oak Bluffs house

3 bedrooms / 2 bathrooms / Sleeps 7

$500

1 / 18

ROLAJ - Waterfront, Waterview, Lagoon Beach, Hi Speed Internet

Oak Bluffs house

4 bedrooms / 2 bathrooms / Sleeps 8

$450

1 / 24

BACOL - Charming Waterview Home, Immaculate Beachy Interior, Spacious Shady Dec

Oak Bluffs house

3 bedrooms / 2 bathrooms / Sleeps 6

$429

1 / 19

THORB - Contemorary 4 Bedroom 4 Bath, Walk to Oak Bluffs Center and Inkwell Beac

Oak Bluffs house

4 bedrooms / 4 bathrooms / Sleeps 8

$286

1 / 28

Beautiful Campground Victorian Home in Oak Bluffs

Oak Bluffs house

3 bedrooms / 2 bathrooms / Sleeps 7

$357

1 / 19

Lovely clapboard home in a private setting in the heart of town

Oak Bluffs house

4 bedrooms / 2 bathrooms / Sleeps 8

$114

1 / 32

PETEO - Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully

Oak Bluffs house

4 bedrooms / 4 bathrooms / Sleeps 8

$429

1 / 34

CHUNM - Oak Bluffs, European Design, Private Yard, Beautifully Decorated, Patio

Oak Bluffs house

2 bedrooms / 1 bathroom / Sleeps 4

$214

1 / 20

MOORR - Adorable Renovated Vacation Home, WiFi, Patio, Large Yard, Central A/C,

Oak Bluffs house

3 bedrooms / 2 bathrooms / Sleeps 6

$200

1 / 14
Viewing 38 of 228

About Oak Bluffs

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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?

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