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Vacation Rentals & Apartments in Oak Bluffs

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Vacation Rentals & Apartments in Oak Bluffs

About Oak Bluffs

1,293 apartments

Adorable Cottage Walking Distance to Town and Beach

Oak Bluffs house

4 bedrooms / 1 bathroom / sleeps 7

Price per night from

$214

1 / 15

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

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 12 minutes

Price per night from

$160

1 / 32

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

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 12 minutes

Price per night from

$177

1 / 31

WATERFRONT HOME WITH PRIVATE BEACH

Oak Bluffs house

7 bedrooms / 4 bathrooms / sleeps 12

“A memorable week at the Vineyard” We had a most enjoyable week - very comfortable accommodation. Everything went smoothly for our son's wedding, even the weather was kind!

Price per night from

$1,000

1 / 25

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$250

1 / 22

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

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 12 minutes

Price per night from

$172

1 / 33

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

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

Oak Bluffs house

1 bedroom / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 12 minutes

Price per night from

$155

1 / 32

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

Oak Bluffs house

1 bedroom / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 12 minutes

Price per night from

$144

1 / 24

BEAUTIFUL SECLUDED ESCAPE WITH CENTRAL A/C

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$625

1 / 10

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

Oak Bluffs house

3 bedrooms / 1 bathroom / sleeps 4

Price per night from

$207

1 / 15

Superb townhouse close to golfing & the beach - deck, tennis, & shared pool

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 12 minutes

Price per night from

$165

1 / 31

COZY,CUTE COTTAGE NEAR TOWN & BEACH.

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$129

1 / 10

Charming cottage with deck and playroom one mile from beach

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 12 minutes

Price per night from

$146

1 / 24

Charming house with lots of entertainment and gourmet kitchen!

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 12 minutes

Price per night from

$143

1 / 24

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

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$286

1 / 29

LIJOY - Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, B

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$357

1 / 34

Oak Bluffs Contemporary Summer Home

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$243

1 / 18

Cozy MV Cottage with Charming Romantic Gardens

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$525

1 / 17

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

Oak Bluffs house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$286

1 / 13

CLARO - New Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$257

1 / 27

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

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$386

1 / 17

“Gingerbread House”, water views, large porch!

Oak Bluffs cottage

4 bedrooms / 1 bathroom / sleeps 8

Price per night from

$400

1 / 12

Spacious Oak Bluffs Condo - Steps to Inkwell Beach

Oak Bluffs apartment

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 55 minutes

Price per night from

$210

1 / 24

OCALC - Adorable Campground Cottage, Overlooks Park , Walk to Town and Ink Well

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$357

1 / 17

Newly Renovated with Fabulous ocean views

Oak Bluffs cottage

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$900

1 / 19

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

Oak Bluffs house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$700

1 / 33

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

QUINTESSENTIAL VINEYARD SUMMER HOME

Oak Bluffs house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$500

1 / 20

BURBR - Perfect Retreat for Large Families, 1.5 miles Oak Bluffs Town Center

Oak Bluffs house

6 bedrooms / 3 bathrooms / sleeps 13

Price per night from

$354

1 / 22

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

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$351

1 / 24

KEEFJ - Historic Waterfront Home Located just 1 Mile from Oak Bluffs Center, Pri

Oak Bluffs house

7 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$3,193

1 / 48

Wonderful Contempory Home in Meadow View Farms

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$400

1 / 30

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. 1 hour 12 minutes

Price per night from

$195

1 / 32

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

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$400

1 / 27

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

4 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$929

1 / 26

BRANF - Exquistie Contemporary Home in Fresh Pond Estates, Screened Porch, ****

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$500

1 / 20

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

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Viewing 38 of 1,293

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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