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Oak Bluffs Rentals

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Oak Bluffs Rentals

About Oak Bluffs

231 apartments

Dog-friendly condo with shared pool & tennis courts - golf and beach nearby!

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 18 minutes

$165

1 / 33

Lovely townhouse w/ private deck, shared pool & tennis - walk to the beach!

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 18 minutes

$197

1 / 31

Charming cottage with deck and playroom one mile from beach

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 18 minutes

$147

1 / 24

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

$145

1 / 20

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

$250

1 / 22

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

Oak Bluffs house

1 bedroom / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 18 minutes

$146

1 / 24

SCHLE - PICTURESQUE WATER VIEWS ACROSS CONSERVATION LAND TO SENGEKONTACKET, SPA

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

$429

1 / 25

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

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 18 minutes

$230

1 / 44

Great Location, Beautiful Home

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

$230

1 / 13

Charming Farmhouse

Oak Bluffs house

4 bedrooms / 1 bathroom / sleeps 8

$400

1 / 17

WONDERFUL VIEWS OF SENGEKONTACKET POND FROM THIS LOVELY VINEYARD HOME

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

$357

1 / 20

Charming house with lots of entertainment and gourmet kitchen!

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 18 minutes

$129

1 / 24

GOLLB - Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi

Oak Bluffs house

3 bedrooms / 1 bathroom / sleeps 4

$193

1 / 15

Seaglass Cottage on East Chop

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

$329

1 / 21

ROBIH - Seaview Condo Unit, Gorgeous Waterviews, In Town Location, Modern updat

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 4

$229

1 / 20

SMYTS - Waterfront, Waterview, Private Beach Lagoon, Wifi Internet

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 7

$229

1 / 21

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

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 4

$221

1 / 20

Summer Vacation Rental

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 8

$300

1 / 11

BEAUTIFUL SECLUDED ESCAPE WITH CENTRAL A/C

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

$625

1 / 10

Cute Guest House Overlooking the Lagoon

Oak Bluffs house

2 bedrooms / 4 bathrooms / sleeps 12

$1,429

1 / 29

“Gingerbread House”, water views, large porch!

Oak Bluffs cottage

4 bedrooms / 1 bathroom / sleeps 8

$400

1 / 12

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

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

$450

1 / 24

Fabulous Gingerbread In The Heart Of OB!

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 2 hours 4 minutes

$489

1 / 23

Cozy townhouse w/ shared pool, tennis & great location close to the beach!

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 18 minutes

$165

1 / 32

Lakefront cottage with a deck, close to ferries & beaches!

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 18 minutes

$123

1 / 37

MCBAA - Walk to Town. Hi Speed Internet.

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

$229

1 / 25

MURPL - Meadow View Farms House, Beautiful Tri- Level Contemporary Spacious Bri

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

$400

1 / 30

Charming Oak Bluffs Cottage within Walking Distance to Town

Oak Bluffs house

6 bedrooms / 3 bathrooms / sleeps 12

$429

1 / 17

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

Oak Bluffs house

3 bedrooms / 1 bathroom / sleeps 5

$257

1 / 13

Walk to Beach from gorgeous Martha's Vineyard home

Oak Bluffs house

6 bedrooms / 3 bathrooms / sleeps 11

$800

1 / 44

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

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

$429

1 / 27

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

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 18 minutes

$114

1 / 32

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

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

$200

1 / 14

Lovely water views of Sengekontacket Pond

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

$571

1 / 22

Tranquil, quiet home w/ private deck - walk to beaches and downtown Oak Bluffs!

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 18 minutes

$208

1 / 32

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

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 4

$193

1 / 11

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

Guest Room in a Cozy Cottage

Oak Bluffs room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 4 minutes

$300

1 / 6
Viewing 38 of 231

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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