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Vacation Rentals & Apartments in Oak Bluffs

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525 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. 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. 3 hours 19 minutes

Price per night from

$224

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$290

BEAUTIFUL SECLUDED ESCAPE WITH CENTRAL A/C

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$715

COZY,CUTE COTTAGE NEAR TOWN & BEACH.

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$129

Oak Bluffs Contemporary Summer Home

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$331

Lovely Oak Bluffs home one mile from town and beach

Oak Bluffs house

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$514

Luxury Oak Bluffs Home with 18 X 30' Pool

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,143

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

4 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$975

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

Oak Bluffs apartment

3 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 18 minutes

Price per night from

$532

“Gingerbread House”, water views, large porch!

Oak Bluffs cottage

4 bedrooms / 1 bathroom / sleeps 8

Price per night from

$458

Beautiful Oak Bluffs Home with Wonderful Waterviews

Oak Bluffs house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$1,438

Cape Style Home near Lagoon Pond- short walk to Lagoon Beach

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$400

CLASSIC, VINTAGE,GINGERBREAD

Oak Bluffs house

7 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$543

OAK BLUFFS VICTORIAN ONE BLOCK FROM BEACH, TWO BLOCKS FROM TOWN!

Oak Bluffs house

6 bedrooms / 3 bathrooms / sleeps 12

“We had a restful time and we laughed alot - the porch was great!” The house was very nice - we had fun laughing and playing games. Proximity to the beach and town was great and all within walking distance. The layout was nice except the difficult steep stairs near kitchen - overall great time.

Price per night from

$571

Guest Room in a Cozy Cottage

Oak Bluffs private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$344

Wonderful Contempory Home in Meadow View Farms

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$429

Summer Vacation Rental

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$418

Enjoy Sea Breezes from third floor roof deck!

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$904

Oak Bluffs Cape Not too Far from Town

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$229

Cute Guest House Overlooking the Lagoon

Oak Bluffs house

2 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$857

Seaglass Cottage on East Chop

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$414

Newly Renovated 2 Bedroom Oak Bluffs House within Walking Distance to Town

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$357

Lovely three bedroom home located in the Hidden Cove area of Oak Bluffs

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$286

Gracious five bedroom in-town Oak Bluffs victorian

Oak Bluffs house

5 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$357

Clean, comfortable ranch with lots of amenities

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$396

Spectacular Martha's Vineyard Island Home!

Oak Bluffs townhouse

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 36 minutes

Price per night from

$453

Charming 4 bedroom home in the east chop neighborhood of Oak Bluffs

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$582

Beautiful Four Bedroom Home Walking Distance to Downtown Oak Bluffs

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$550

Beautiful Main & Guest house short walk to Lagoon Pond

Oak Bluffs house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$571

Adorable Oak Bluffs Cottage Walking Distance to Town

Oak Bluffs house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$285

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

ENJOY WATERVIEWS OF SENGENKONTACKET POND FROM THE WONDERFUL DECK

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$257

Completely Renovated Cottage Close to Town

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$643

Beautiful Oak Bluffs home on Lagoon Pond with Pool!

Oak Bluffs house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$571

Ocean Park Victorian Carousel House

Oak Bluffs house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$975

Four bedroom Oak Bluffs Home

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$357

Beautiful Four Bedroom Home with Central Air Conditioning

Oak Bluffs house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$446

COME EXPERIENCE THE MAGIC OF THE VINEYARD

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

“Great Time!” The house and furnishings were very nice. The beds were a little hard, which could easily be fixed by an egg-carton type pad. The utensils in the kitchen were not good for cooking, they melted every time they touched the pan. The grill could use a major cleaning, and also having a grill brush handy would be ideal. For some reason while we were there, the queen size bedroom's electric didn't work, but it was not a big deal for us, because we didn't use that room at all. There's a fire pit, but we had no idea where to get firewood to build a fire. Flyers or phone numbers would have helped. Also we were 'supposed' to have bicycles with the rental, and we couldn't find them. I emailed the owners, and he called me right away saying it was a liability to have bikes with the property. Very understandable. That's the reason we chose this house, because it had so many of the things we needed/wanted. But we rented bikes for two days and the owners reimbursed us, because it was advertised as having bicycles with the property. There was a pack-n-play and a high chair and booster seat. That's very helpful with an 11 month old little girl. Overall it was a great experience and we would definitely stay here again if we vacation on the Vineyard in the future!

Price per night from

$400

Viewing 38 of 525
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

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
CLASSIC AND CHARMING COTTAGE WALKING DISTANCE TO THE BEACH AND TOWN
Great!

The home was large enough to accommodate everyone. Our family had a fantastic time! … 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, AC, WiFi, Sleeps 22, 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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