Oak Bluffs Vacation Rentals

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BICKE

East Chop Area, Tri-Level Home with Distant Water views, Located just 1.5 Mi to Oak Bluffs Center

Beautiful summer home with distant water views, located in the desirable East Chop neighborhood. This 4 bedroom, 3 bath home is located just 1.5 miles from Oak Bluffs Center & Beach.

The...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$6,500 - $7,150

Clean Fee:

$600 per week

Tax: State & Local:

11.7

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BURBS

Set Just on the ouskirts of Oak Bluffs. Central AC, Screened Porch

Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs center and beach area. Fully furnished screen porch and shady porch. This lovely home sleeps families of 8 comfortably.

The main...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$5,500 - $7,000

Clean Fee:

$425 per week

Tax: State & Local:

11.7

Transferrable Ferry Tickets available, 7/13 -7/20 & 7/20 -7/27. Please inquire for details!

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HANRJ

Spacious Oak Bluffs Contemporary Home, 4 Bedrooms & 4 Baths, Quiet Private Location in Bayes Hill Community of Homes

Privately situated on the outskirts of Oak Bluffs, yet centrally located to towns and beaches. The home features a large patio area with outdoor dining and grill area and a spacious...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$3,000 - $7,000

Clean Fee:

$575

Tax: State & Local:

11.7

Owner reduced rates for available weeks in June, July & August - see calendar for adjusted rates

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BEG21

Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC

This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$3,500 - $7,000

Clean Fee:

$400 per week

Tax: State & Local:

11.7

Ferry Tickets Available for weeks 7/19-7/26 & 7/26-8/2 - please inquire

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HOL14

Gorgeous Waterfront Home on the Lagoon Oak Bluffs, Kayak, Swim, Enjoy the Sunsets, 4 bedrooms 4.5 Baths

Stunning Waterfront home nestled just in the outskirts of Oak Bluffs, 1 mile from town center and Oak Bluffs beaches. This home offers 150 feet of private lagoon beach perfect...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$5,000 - $7,000

Clean Fee:

$750 per week

Tax: State & Local:

11.7

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BRANF

Spacious Colonial with Contemporary Detailing in Fresh Pond Estates, Mulitpe Living Spaces, Screened Porch, Spacious Deck, AC, Wifi, Beautifully Furnished, Bike Paths at the head of the Road

Spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. . The main living level features an open concept and hosts a family...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$4,900 - $6,900

Clean Fee:

$500 per week ($350 for interim cleaning on multiple week rentals)

Tax: State & Local:

11.7

Ferry Tickets Available 8/24-8/31 - please inquire

Rate just reduced for 8/24 week - see calendar for adjusted rate

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GUCOB

Spacious Home with Heated Pool, Pool Bar with TV, Patio Surround, Deck Overlooking the Pool & Yard, Centrally Located

Spacious home with private heated pool & hot tub, tucked away in a quiet neighborhood, centrally located providing easy access to beaches and towns. The pool, patio area, deck, & pool bar...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$6,820 - $6,820

Clean Fee:

$400 per week

Tax: State & Local:

11.7

Pool Heated to 80 degrees included in the rental rate, July & August

Pool Heated to 80 degrees, June & September, additional 350 per week surcharge

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FISHJ

Stylish Contemporary Vacation Home situated in Meadow View Farms, Open Light Filled Design, Expansive Private Deck

Come and enjoy this light-filled, beautifully maintained, three-level contemporary home complete with gardens, landscaped yard, and a children’s backyard playground.

The main level features an open kitchen, dining, and TV/living...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$3,900 - $6,800

Clean Fee:

$425 per week

Tax: State & Local:

11.7

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LECAY

Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bedrooms, 15 Minute Walk to Oak Bluffs Center and Inkwell Beach

All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, all just a...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$4,500 - $6,500

Clean Fee:

$400 per week

Tax: State & Local:

11.7

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LIJOY

Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, Bike Paths at Entrance to Neighborhood, Multiple Beaches Near By

Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$4,700 - $6,500

Clean Fee:

$390 per week

Tax: State & Local:

11.7

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JOSEJ

Exquisite Coastal Style Home, Pool, Patio, Landscaped Yard! 10 minute walk to Oak Bluffs Center, Luxury Interior, 3 bedrooms, 4 baths, Multiple Living Spaces

This newly constructed, luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with varying depths of 3 to 8 feet, a...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$6,500 - $6,500

Clean Fee:

$700 per week

Tax: State & Local:

11.7

Rates just reduced for available weeks in July & August by 15% - see calendar for adjusted rates

Pool Heated to 81 degrees included in rental rate last Sat in June to first Sat in September. Pool Depth 3 feet to 8 Feet

Pool Heated to 81 degrees June and September weeks additional $275 per week

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Front of House , Wraparound Farmer's Porch

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THOMS

New Modern Farmhouse Design, Great Location!, Wraparound Farmers Porch, Deck Area.

Beautiful new 4 bedroom home, 3.5 bath sleeps 8. Ideally located just 2 miles from the center of Oak Bluffs and just minutes by car to the towns of Vineyard Haven and...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$3,100 - $6,300

Clean Fee:

$425 per week

Tax: State & Local:

11.7

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WHARG

Lovely Home in a quiet Neighborhood. Walk to Town Center and Inkwell Beach, Large Private Deck, Room AC

Spacious sun-filled contemporary home located on a quiet private street, a 10-minute walk to town center, Inkwell Beach, and the harborfront.

The first level features a spacious kitchen with stainless steel...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$6,300 - $6,300

Clean Fee:

$375 per week

Tax: State & Local:

11.7

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CLARO

Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch & Farmers Porch, Deck, Lovely Yard Area, Bike or Walk to Oak Bluffs Center.

Situated just on the outskirts of Oak Bluffs, this lovely vacation home offers renters modern styling with multiple living spaces and all the conveniences renters look for in a vacation home....Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$2,800 - $6,100

Clean Fee:

$450 per week

Tax: State & Local:

11.7

New Bedrooms 3 & 4, in the lower level, and bath are not available in 2025 for the weeks 7/5 & 8/23 and September. Occupancy limit is 6, 2 Bedrooms 1st and 2nd Level. Sleep sofa and a day bed in the 2nd level family room. Rates listed reflect this arrangement for 2025. Inquire with Agent for details.

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NEWMJ