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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Seaview Condominium, Waterview, Walk to Town and Beach

Beachfront Condominium with breathtaking views of Nantucket Sound. Just steps to the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$0 - $0
June 2026
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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ST304

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Sea View Condominium, Water View, Walk to town and beach

Sea View Condominium with a breathtaking view of Nantucket Sound from almost every room. Just steps from the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$0 - $0
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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FRIEM

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Beautiful East Chop Home , Walk to Town & Beach, Outdoor Patio Area with Patio Dining

Lovely Spacious East Chop Area home features elegant custom craftsmanship throughout, a light-filled open kitchen, living and dining areas, and a family/TV room. 3 bedrooms on the 2nd level and 2...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
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ALLER

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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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 $4,200
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
Add Favorite
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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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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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July 2026
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August 2026
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September 2026
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$3,500
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 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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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 $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
June 2026
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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CAH48

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Property Details
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: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$2,700
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$2,700
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$2,700
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$2,700
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 $3,500
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 $2,700
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$2,700
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Clean Fee: 
$300, additional may apply multiple week rentals
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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 $7,400
July 2026
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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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$11,500
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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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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
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

 

Add Favorite
 
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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
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July 2026
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August 2026
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$8,500
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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
Add Favorite
 
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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
SuMoTuWeThFrSaWeek
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2
3
4
5
6
$3,750
7
8
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$3,750
14
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$4,350
21
22
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$4,600
28
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 $5,400
July 2026
SuMoTuWeThFrSaWeek
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2
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$5,400
5
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$5,400
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$5,600
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$5,600
26
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 $5,600
August 2026
SuMoTuWeThFrSaWeek
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$5,600
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$6,850
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$6,850
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$6,850
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$6,350
30
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 $3,750
September 2026
SuMoTuWeThFrSaWeek
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$3,750
6
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$3,750
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$3,750
20
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$3,750
27
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29
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 $3,750
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
Add Favorite
 
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LORJU

(0)Inquire/Share
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
SuMoTuWeThFrSaWeek
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$13,500
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$13,500
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$13,500
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$13,500
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 $13,500
July 2026
SuMoTuWeThFrSaWeek
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$13,500
5
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$13,500
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$13,500
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$13,500
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 $15,000
August 2026
SuMoTuWeThFrSaWeek
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$15,000
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$15,000
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$15,000
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$15,000
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$13,500
30
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 $13,500
September 2026
SuMoTuWeThFrSaWeek
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$13,500
6
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$8,000
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$8,000
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$8,000
27
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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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