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Vacation Rentals & Apartments in Oak Bluffs

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Vacation Rentals & Apartments in Oak Bluffs

About Oak Bluffs

1,282 apartments

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

Price per night from

$145

1 / 20

WOODO - Weku House, Luxury Living, Features Outstanding Entertainment Level, Gu

Oak Bluffs house

6 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,286

1 / 43

Hidden Gem in Oak Bluffs with Private Tennis

Oak Bluffs house

3 bedrooms / 3 bathrooms / sleeps 6

“Awesome Vacation Experience” 8 Gorham Ave was a beautiful home for our summer vacation in 2009. With the three bedrooms, expansive kitchen, long back porch with grill, jacuzzi in the master bath, and BONUS*** tennis courts, we spent the most relaxing

Price per night from

$529

1 / 20

WIGGE - Adorable Cape Style Home, Situated on a Quiet Side Street, 15 Minute W

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$286

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

Price per night from

$193

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Coastal getaway w/ shared outdoor pool & 3 tennis courts - 1/2 mile to the beach

Oak Bluffs house

1 bedroom / 2 bathrooms / sleeps 6

Price per night from

$81

1 / 32

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

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$77

1 / 32

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

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$87

1 / 31

New construction w/ patio & yard - walk to the ferry, downtown & beaches!

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$124

1 / 32

WONDERFUL,SPACIOUS, LOVINGLY MAINTAINED HOME IN SENGEKONTACKET AREA

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$286

1 / 18

SMEDM - Retreat to this Lovely Vacation Home with Main and Guest House, Central

Oak Bluffs house

7 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$500

1 / 40

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

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$88

1 / 33

ENJOY WATERVIEWS OF SENGENKONTACKET POND FROM THE WONDERFUL DECK

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$243

1 / 21

Enjoy the charm of a Vineyard cottage with all the amenities of today

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$229

1 / 18

Newly Renovated with Fabulous ocean views

Oak Bluffs cottage

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$800

1 / 19

Lovely water views of Sengekontacket Pond

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$429

1 / 22

WESTW - Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sen

Oak Bluffs house

5 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$364

1 / 35

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

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,143

1 / 38

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

Oak Bluffs house

1 bedroom / 2 bathrooms / sleeps 6

Price per night from

$81

1 / 24

Charming cottage with deck and playroom one mile from beach

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$126

1 / 24

LECAY - Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bed

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$429

1 / 15

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

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$286

1 / 28

Price per night from

$193

1 / 9

FULMC - Oak Bluffs, Updated Coastal Decor, Set just on the Outskirts of Central

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$329

1 / 22

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

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$201

1 / 41

CLASSIC AND CHARMING COTTAGE WALKING DISTANCE TO THE BEACH AND TOWN

Oak Bluffs house

5 bedrooms / 2 bathrooms / sleeps 10

“Great!” The home was large enough to accommodate everyone. Our family had a fantastic time!

Price per night from

$200

1 / 14

Charming Oak Bluffs Cottage within Walking Distance to Town

Oak Bluffs house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$429

1 / 17

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

Oak Bluffs house

6 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$571

1 / 27

CHARMING COTTAGE-WALK TO TOWN & HARBOR!

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$239

1 / 13

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

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$400

1 / 28

CORSB - Outstanding Luxury Waterfront, Dock, Wifi Internet, A/C

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$843

1 / 24

RUTHW - Lagoon Waterview, Central AC, 200 Yards to Private Assoc Lagoon Beach,

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$314

1 / 21

BICKE - East Chop, Waterview, Central Air, Wifi Internet

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$721

1 / 20

SCHUS - Waterfront, Waterview

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$429

1 / 12

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

Oak Bluffs house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$571

1 / 23

Wonderful Spacious Oak Bluffs Home with Heated Pool

Oak Bluffs house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$714

1 / 37

Victorian jewel on sought after Ocean Park in Oak Bluffs

Oak Bluffs house

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$714

1 / 27

Oak Bluffs Contemporary Summer Home

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$243

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Viewing 38 of 1,282

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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