Oak Bluffs Vacation Rentals

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KEANM

Lovely Oak Bluffs Home, 3 Bedrooms, 2.5 Baths, Sleeps 7. Set just on the Outskirts of Oak Bluffs Center

Lovely 3 bedroom, 2.5 bath home that sleeps 7. This sweet home is bordered by a large yard and is located just on the outskirts of Oak Bluffs. The patio...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$2,500 - $4,700

Clean Fee:

$500 per week

Tax: State & Local:

11.7

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VANAL

Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and Town Center,

Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. The main living level features a lovely kitchen, very well stocked with...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$3,000 - $4,500

Clean Fee:

$350 per week

Tax: State & Local:

11.7

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WILCM

Hidden Cove, Association Tennis Courts, 3 Bedrooms, 2.5 Baths, Screened Porch and Deck

Nestled in the charming Hidden Cove community, this adorable contemporary home resides on a tranquil street within walking distance of the association's tennis courts. Its central location places it just...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$3,800 - $4,500

Clean Fee:

$325 per week

Tax: State & Local:

11.7

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COONC

The Boathouse, East Chop Location, Gorgeous Water and Sunset Views, Architect Designed Gem

Designed by a renowned island architect and custom-crafted, The Boathouse underwent construction and total renovation in 2016 and is now a terrific year-round home. The exterior of the house maintains...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$4,400 - $4,400

Clean Fee:

$400 per week

Tax: State & Local:

11.7

Two-week minimum stay per owner!

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ROLAJ

Waterfront, Water View, Lagoon Beach

This charming, recently renovated, waterfront home atop the lagoon bluffs, boasts spectacular sunsets and panoramic waterfront views of the Lagoon, outer Vineyard Haven Harbor, and Cape Cod from patios, living...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$4,000 - $4,200

Clean Fee:

$250 per week

Tax: State & Local:

11.7

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PETEV

Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association Tennis Courts, AC, Wi-fi, Bike Paths Nearby

Note: Pricing for this waterfront home takes into account that this is an older-style home. Please note that baths and kitchen have not been updated

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$2,460 - $4,100

Clean Fee:

$475 per week

Tax: State & Local:

11.7

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Expansive deck with Sectional Sofa, Chaise Lounge Chairs, Patio Dining and Grill

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TERSM

Modern, Newly Renovated, Architecturally Significant Beach Cottage Design. Close to Town and Beaches, Tucked in the Lovely Community of Summer Homes, Waterview Farms!

Gorgeous all newly renovated and newly furnished mid-century beach cottage, now a modern vacation oasis designed by the prominent interior design firm, - Tersigni Palachek. This eloquent, yet beachy home offers...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$2,600 - $4,100

Clean Fee:

$425 per week

Tax: State & Local:

11.7

Rate reduced for week 7/11-7/18 - see calendar for adjusted rates

Owner books Fri to Fri July & August weeks!

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CENCR

Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Great Area for Kayaking.

Spacious sun-filled home features open living spaces, hardwood floors throughout, 4 bedrooms and sleeps 8.

Exterior features include two decks, one sunny deck at the front of the house, and a large private...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$3,000 - $4,000

Clean Fee:

$480 per week

Tax: State & Local:

11.7

Rates just reduced on available weeks - see calendar for adjusted rates

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CAH48

Classic Lovely Vineyard Cottage, Pristine Condition, Approximately 1.5 Miles to Town and Beaches. Mature Landscaped Yard, Spacious Deck

The Perfect Cozy Cottage, is pristinely maintained and situated in a quiet neighborhood just on the outskirts of Oak Bluffs. This spacious 2 bedroom, 2 bath home sleeps 4. The...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$2,700 - $4,000

Clean Fee:

$300, additional may apply multiple week rentals

Tax: State & Local:

11.7

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THORB

Contemporary 5 Bedroom 4 Bath, Multiple Living Spaces, Walk to Oak Bluffs Center and Inkwell Beach-10 minutes

Extended families are sure to enjoy this tri-level home featuring an open floor plan on the main level, a large main living room, and three den/TV areas, one on the first level...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$2,700 - $3,800

Clean Fee:

$500 per week

Tax: State & Local:

11.7

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ROBIH

Seaview Condo Unit, Gorgeous Water Views, In Town Location, Modern updated Interior!

Note: Seavies Condos is a 3-minute walk from the Steamship Authority dock in Oak Bluffs and two blocks from the Island Queen ferry dock. Perfect location if you cannot or...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$1,950 - $3,800

Clean Fee:

$230 per week

Tax: State & Local:

11.7

5 minute walk from Steamship Authority Oak Bluffs dock to the Seaview Condos. 2 blocks from the Island Queen ferry dock.

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KNOXA

Modern Cottage, Recently Updated! Walk to Oak Bluffs Harbor and Town Center, 15 min walk

Walk to Oak Bluffs town center, ferry, or Inkwell Beach from this beach-chic recently renovated, adorable cottage!

Upon entering you are greeted with an open floor plan in the living, kitchen,...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$3,150 - $3,800

Clean Fee:

$300 per week

Tax: State & Local:

11.7

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FRANL

Modern, Light filled Home, Located at end of Quiet Street, 1.5 Miles to Oak Bluffs center, Harbor Area and one of many Public Beaches

Perfect Oak Bluffs vacation home. Located just 1.5 miles to the village center, town beach, and centrally located to the towns of Vineyard Haven, Edgartown, and multiple public beaches. This...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$2,300 - $3,600

Clean Fee:

$400 per week

Tax: State & Local:

11.7

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SACHE

Waterview Farms, Water view

Lovely contemporary home in one of the island's premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches....Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$3,000 - $3,500

Clean Fee:

$250 per week

Tax: State & Local:

11.7

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MAHAB