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:
$0 - $0
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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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
June 2026
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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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
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July 2026
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$7,400
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$7,400
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 $8,500
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$11,500
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 $5,000
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Clean Fee: 
$450 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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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

 

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BARNJ

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Property Details
Chic, Meticulously Maintained Cape Style Home, 3 bedrooms, 3 Baths, Sleeps 6, Walk to Oak Bluffs Town Center and Beaches, Tucked on a Large Beautifully Landscaped Lot

Nestled in a beautifully landscaped lot in a serene and private neighborhood, this meticulously maintained cottage in Oak Bluffs offers a perfect retreat for rental guests. With chic luxury amenities, it's...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$0 - $0
June 2026
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$5,600
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 $5,600
August 2026
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 $3,750
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 $3,750
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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LORJU

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Property Details
Stunning Oak Bluffs Luxury Home with Heated Pool, Multiple Living Areas, Walk to Town 8/10ths mile from house.

This charming tri-level home is nestled on a peaceful street in the heart of Oak Bluffs, just a 10 to 15-minute walk from the town center, Inkwell Beach, Town Beaches,...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$0 - $0
June 2026
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July 2026
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$13,500
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$13,500
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 $15,000
August 2026
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$15,000
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 $13,500
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$8,000
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Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Pool Heated to 82 degrees, included in the rental rate!

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