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Vacation Rentals & Apartments in Oak Bluffs

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1,311 apartments

Adorable Cottage Walking Distance to Town and Beach

Oak Bluffs house

4 bedrooms / 1 bathroom / sleeps 7

Price per night from

$214

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

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

$248

Charming house with lots of entertainment and gourmet kitchen!

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$241

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$287

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. However, everything from the ease of reservation, kindness of staff, attentiveness to our concerns, and extreme hospitality made this a wonderful and memorable stay. The concerns about the noise are real, but wasn't an issue for us and I'm fairly noise sensitive. The location is beyond ideal, the property beautifully decorated, cleaned and maintained, and the proximity issue was actually quite pleasant after all our years of visiting the island. As a side note Larry's hospitality is beyond measure for so many reasons I can't name them all here. The bottom line...I would recommend this property to anyone and everyone, definitely a winner.

Responds fast! avg. 1 hour 5 minutes

Price per night from

$178

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

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$357

Ground-floor condo w/ shared pool & tennis courts, close to golfing & the beach!

Oak Bluffs house

1 bedroom / 2 bathrooms / sleeps 6

Price per night from

$204

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

$252

Oak Bluffs Contemporary Summer Home

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 22 minutes

Price per night from

$287

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

Oak Bluffs house

3 bedrooms / 1 bathroom / sleeps 4

Price per night from

$214

Cozy MV Cottage with Charming Romantic Gardens

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$602

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

$273

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

BEAUTIFUL SECLUDED ESCAPE WITH CENTRAL A/C

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$717

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

$212

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

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

Luxury Oak Bluffs Home with 18 X 30' Pool

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,143

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

Oak Bluffs house

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$300

Charming cottage with deck and playroom one mile from beach

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$164

Spacious Oak Bluffs Condo -Steps to Inkwell Beach

Oak Bluffs apartment

3 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 4 minutes

Price per night from

$343

“Gingerbread House”, water views, large porch!

Oak Bluffs cottage

4 bedrooms / 1 bathroom / sleeps 8

Price per night from

$459

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

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

Oak Bluffs house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$231

COZY,CUTE COTTAGE NEAR TOWN & BEACH.

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$129

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

$586

BRANF - Spacious Colonial with Contemporary Detailing in Fresh Pond Estates, Sc

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$450

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

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

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

Oak Bluffs house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$529

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

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$429

RUTHW - Lagoon Waterview, Central AC, 200 Yards to Lagoon, Swim and Kayak

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$314

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

4 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$1,066

QUINTESSENTIAL VINEYARD SUMMER HOME

Oak Bluffs house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$500

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

LEHNP - Beach Front East Chop Cottage, Spectacular Views, Perfect Getaway Cott

Oak Bluffs house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$179

Wonderful Contempory Home in Meadow View Farms

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$400

Viewing 38 of 1,311
rentals in Oak Bluffs

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About Oak Bluffs

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?

Top Destination reviews

Historic home with gorgeous antiques and modern conveniences
Oak Bluffs Locale

Older home with antique furnishings and flea market finds offers great location and ambience for visitors to Oak Bluffs. Front porch seating points an eye to the park and ocean and gives an opportunity to speak to walkers and bikers passing by. Sometimes it's all about location and less about modern updates.see more
Oak Bluffs Contemporary Summer Home
Great location

The location is great especially if you have teenagers. They can make their way to town with or without you. The layout is a little quirky but overall nice. The house overall was true to the posting. Cons: there wasn't any storage for non-perishable food in the kitchen. The posting should include bringing your own sheets and towels. Use of the washer and dryer would be nice and the downstairs area had moisture issues. Overall I would recommend the house to friends.see more
In-Town Historic Property on Martha's Vineyard
Perfect!

My sister and I stayed in Unit 1 and had a fabulous time. We were pleasantly surprised at how nicely furnished, roomy, and well maintained it was. The kitchen is large and has everything needed for preparing meals. It is perfectly located right on Circuit Avenue, and is a short walk down to the harbor. We especially enjoyed the large balcony facing the street. Although it's located right above Sharkey's Restaurant, we hardly heard any noise. The owner and caretaker were very accessible if we needed anything. We can't wait to stay again next year.see more
Adorable GINGER BREAD house on MV..NICE !!!
Wonderful cottage

We have just returned from a wonderful week at Tranquility Cottage. Our stay was perfect. The cottage contained everything we needed. The downstairs was much more spacious than it appeared in the photos. Location could not have been better. Located in the peaceful surrounds of the Campground, yet within close walking distance of the harbor, Circuit Avenue and Ocean Park. The owner, Mike Mitchell, was very accommodating prior to our trip with very useful info about the cottage. He was a pleasure to deal with. I would highly recommend this cottage to my friends and family.see more
Heated Pool, Hottub,AC,WiFi,sleep22, 2 mi to beach
very happy with our choice

There are 4 bathrooms in main house, and one outside shower. I have never been in a property that was so well stocked. There was a sewing kit in a night stand. There are beds everywhere. Two down in the cellar, two in the TV room, one in the kitchen. Master bedroom had a king and a single bed in room. Two beds in walk in closet. The rest of bedrooms had full to queen size beds. There were three refrigerators two in garage, and one in kitchen. Plenty of sitting for large group. There were nicely landscaped grounds all around the house. Plenty of privacy from any neighbors.see more
Lovely Oak Bluffs home one mile from town and beach
we had a blast

the house was nice we loved it, it could use a little tlc but even as is I would recommend this place, nice quiet street close to everything,also the amenities were fablous … see more

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