Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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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: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$14 - $10,003
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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ROSKH

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Property Details
East Chop Classic Waterfront Home, Private Dock, Mooring Available, Spectacular Sunsets

Experience the epitome of summer living at East Chop Oak Bluffs in this delightful waterfront retreat. Nestled amidst the serenity of the beachfront, this cozy home boasts a private dock...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$14 - $10,003
June 2025
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Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Ferry Tickets Available,  7/26 to 8/2.  Please inquire for details!

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LONAJ

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Property Details
Luxurious Oak Bluffs Home, Multiple Living Spaces, Deck Dining Area. 3 Bedrms, Sleeps7

Welcome to this exquisite, contemporary, luxurious Oak Bluffs residence. Nestled on a tranquil street on the periphery of Oak Bluffs, this 3-bedroom, 2.5-bathroom home boasts opulent accents throughout.

Upon entry...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$14 - $9,205
June 2025
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

 

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COONC

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Property Details
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: 
4
Bedrooms: 
3
Baths: 
2
Price Range:
$14 - $9,002
June 2025
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Two-week minimum stay per owner! 

 

 

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VANA2

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Property Details
Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$14 - $8,505
June 2025
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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PRIAN

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Property Details
Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$14 - $8,302
June 2025
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Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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LECAY

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Property Details
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: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$14 - $8,001
June 2025
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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BEG21

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Property Details
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: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$14 - $8,001
June 2025
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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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CORAG

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Property Details
Lovely, Newly Updated Oak Bluffs Home. Multiple Indoor/Outdoor Living/Lounge Areas, Sleeps 8, 10/15 minute Walk to the Vilage Center.

Note: All photos are virtually staged photos by the owner, all new furnishings will be arriving throughout the winter months. 

Welcome to Noble House, a beautifully updated home nestled in a charming neighborhood just...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
3
Baths: 
2
Price Range:
$14 - $8,001
June 2025
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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BURBR

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Property Details
Perfect Retreat for Large Families, 1.5 miles to Oak Bluffs Town Center & Beach, Bike Path at end of Street

Spacious and perfect for extended families, featuring multiple attractively furnished living areas, and sleeps 13 comfortably. The lower level of the house features a queen bed, kitchenette, den area with...Read more

Location: 
Oak Bluffs
Sleeps: 
11
Bedrooms: 
5
Baths: 
3
Price Range:
$14 - $7,952
June 2025
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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CASHK

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Property Details
Lovely Home, Centrally Located, Bike Paths, AC all Rooms

This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window AC in all rooms, and a well-equipped modern kitchen. The home is nicely situated...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$14 - $7,805
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Clean Fee: 
$200 per week
Tax: State & Local: 
11.7
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PETEO

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Property Details
Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully Landscaped

Outstanding vacation home, centrally located to all three down-island town centers and multiple public beaches. This lovely home in a serene setting overlooks the picturesque Little Duarte Pond in the Iron Hill...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
5
Price Range:
$14 - $7,602
June 2025
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Clean Fee: 
$575 per week
Tax: State & Local: 
11.7
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VANAL

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Property Details
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: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$14 - $7,504
June 2025
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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DENAL

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Property Details

Charming, 4-bedroom Oak Bluffs Home, pristinely maintained!  The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$14 - $7,504
June 2025
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July 2025
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August 2025
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September 2025
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Parking for two cars only, no on-street parking!

 

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Property Details
"Endless Summer Vacation" Stylish, Newly Update 3 + Bedroom, Sleeps 8, East Chop Area of Oak Bluffs, Deck Living & Dining Area, Screened Porch,
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$14 - $7,504
June 2025
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July 2025
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August 2025
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September 2025
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Clean Fee: 
$330 per week
Tax: State & Local: 
11.7

Owner will rent off weekend dates to accommodate the need for ferry tickets July weeks. 

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