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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Stunning Tri-Level Home, Heated Pool, Screened Porch, Beautifully Landscaped, Walk to Association Tennis Courts

Featured MVVR Listing:

Beautiful Coastal Inspired Retreat features multiple living spaces, a pool, a bluestone patio area, and a deck with an outdoor dining and grill area.  This beautiful home is...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$70 - $70
June 2026
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees included in rental rate last Saturday in June to the first Saturday in September. 

 

Pool Heated to 80 degrees, June & September weeks additional $300 propane surcharge per week. 

   

 

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HUN24

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Property Details
Gorgeous Waterfront Home, Stunning Views, Spacious Vacation Home, Perfect for Extended Family & Friends
Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$70 - $70
June 2026
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Clean Fee: 
Tax: State & Local: 
11.7
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ALVEN

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Property Details
Spacious Oak Bluffs Home, Heated Pool 16 x 32, 4 bedrooms & 3.5 baths sleeps 8

This charming and spacious 4-bedroom, 3.5-bath home offers multiple living areas, including a main living room with TV, a cozy sitting room, and a lower-level family room featuring a TV,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
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Clean Fee: 
$550
Tax: State & Local: 
11.7

Two week minimum stay required, house can be rented Sat 8/8 to 8/22 or 8/9 to 8/23

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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:
$0 - $0
June 2026
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Clean Fee: 
$200 per week
Tax: State & Local: 
11.7
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ALLER

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Property Details
Oak Bluffs 4 Bedroom Home, Walk to Town & Beach!

10-minute walk to Oak Bluffs center and beach area from this lovely modern vacation home.  Enjoy all that the summer community of Oak Bluffs has to offer with quaint shops,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2026
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 $5,250
August 2026
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 $4,500
September 2026
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$4,500
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$4,200
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$4,200
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 $4,200
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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ROLAJ

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Property Details
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: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2026
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Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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FISHJ

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Property Details
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: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$0 - $0
June 2026
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Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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TRAVM

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Property Details
Updated East Chop Area Summer Retreat, Great Proximity to Town Center and Beaches, Cottage Styling with All the Modern Amenities, Central A/C. Covered Porch and Open Patio Areas.

Visitors will enjoy this delightful &  comfortable 4 bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. 

Relax in the breeze with your morning coffee on the front...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2026
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 $5,350
July 2026
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 $7,000
August 2026
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$7,200
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$7,500
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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MAHAB

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Property Details
Sweet Updated 3 Bedroom Home, Nicely Tucked in Lightly Wooded Area, Central Location, Beaches and Towns just a short Drive!

Lovely reverse contemporary home with a large deck, outdoor dining, and grill area. The upper level of this home features an open kitchen, living, and dining area stylishly furnished.  Nicely equipped kitchen...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
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$4,000
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 $4,000
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September 2026
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$4,000
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$3,500
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$3,500
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 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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LANLL

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Property Details
Outstanding Waterfront Home & Guest House, Panoramic Views, Beach on the Lagoon, 5 Bedrooms, 4 Baths, AC

Gorgeous Expansive Waterfront Main & Guest Cottage, perfect for a multigenerational family vacation.  Spectacular views across and up the lagoon, this pristine home and guest cottage sits on just under two...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
4
Price Range:
$0 - $0
June 2026
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August 2026
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$18,000
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$18,000
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$15,500
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 $15,500
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$15,500
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Two Week Minimum Stay Required per Owner

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NEWMJ

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Property Details

Newly update mid-century modern beach house set in the private community of homes surrounding Sengekontacket pond. The cozy summer cottage offers indoor and outdoor living at its best with a...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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STEJE

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Property Details
Charming Oak Bluffs Home, Waterfront on the Lagoon, Patio & Deck Areas. Spectacular Views & Sunsets

Waterfront on the Lagoon! The highlight of this home is its breathtaking views across the lagoon and beautiful sunsets. Whether you're inside or outside on the deck or patio, you can...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$5,000
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$5,000
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 $7,400
July 2026
SuMoTuWeThFrSaWeek
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$7,400
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$7,400
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$7,400
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$7,400
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 $8,500
August 2026
SuMoTuWeThFrSaWeek
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$8,500
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$10,500
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$10,500
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$11,500
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 $5,000
September 2026
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$5,000
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MANUC

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Property Details
Hart Haven, Spacious Contemporary Colonial, Private Association Beach .8 mi from house, Private Association Tennis, 5 min walk from house

Located in the desirable enclave of homes known as Hart Haven just on the outskirts of Oak Bluffs Center, rental guests will surely enjoy this beautifully maintained home bordered by...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
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$10,000
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$10,000
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$10,000
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$10,000
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 $10,000
July 2026
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$10,000
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$10,000
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$10,000
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 $10,000
August 2026
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$10,000
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$11,000
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$11,000
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$11,000
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 $10,000
September 2026
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$10,000
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$10,000
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$10,000
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 $10,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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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:
$0 - $0
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

 

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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:
$0 - $0
June 2026
SuMoTuWeThFrSa
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July 2026
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August 2026
SuMoTuWeThFrSaWeek
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$8,500
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$8,500
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$6,500
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September 2026
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

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