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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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:
$3,900 - $3,900
June 2026
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Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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THORB

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Property Details
Contemporary 5 Bedroom 4 Bath, Multiple Living Spaces, Walk to Oak Bluffs Center and Inkwell Beach-10 minutes

Extended families are sure to enjoy this tri-level home featuring an open floor plan on the main level, a large main living room, and three den/TV areas, one on the first level...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$2,700 - $3,800
June 2026
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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KOEOB

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Property Details
Adorable Updated 2 Bedroom 1.5 Bath Cottage, Walk to Town, Harbor and Beach

If you are looking for an adorable cottage-style home in the center of Oak Bluffs this newly updated, tastefully decorated 2 bedroom, with one full bath and a half bath, is sure to...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$2,500 - $3,800
June 2026
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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FRANL

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Property Details
Modern, Light filled Home, Located at end of Quiet Street, 1.5 Miles to Oak Bluffs center, Harbor Area and one of many Public Beaches

Perfect Oak Bluffs vacation home.  Located just 1.5 miles to the village center, town beach, and centrally located to the towns of Vineyard Haven, Edgartown, and multiple public beaches.  This...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$2,300 - $3,600
June 2026
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 $2,300
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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ST203

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Property Details
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: 
5
Bedrooms: 
2
Baths: 
2
Price Range:
$2,900 - $3,300
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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LODGJ

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Property Details
Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet
Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,900 - $2,900
June 2026
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Clean Fee: 
$360 per week
Tax: State & Local: 
11.7
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ST304

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Property Details
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: 
5
Bedrooms: 
2
Baths: 
2
Price Range:
$2,900 - $2,900
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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GOLLB

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Property Details
Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi

MVVR EXCLUSIVE:  Classic, beach cottage with spectacular views across the sound, calm water swimming, and a great area for kayaking. The open kitchen, dining, and living areas are enhanced by the wall of windows...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
1
Price Range:
$1,850 - $2,700
June 2026
SuMoTuWeThFrSaWeek
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Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

Cottage books Tuesday to Tuesday July & August weeks

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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
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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
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Clean Fee: 
$200 per week
Tax: State & Local: 
11.7
Add Favorite
friem09 - 04 - ext.jpg
 
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FRIEM

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Property Details
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
Add Favorite
 
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KLEIB

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Property Details
Lagoon Waterfront & Beachfront, Spectacular Water views, Room A/C, WIFI

Adorable waterfront & beachfront cottage.   Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to a...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$0 - $0
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Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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GRACM

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Property Details
Beautful Oak Bluffs Home. Pool, Tucked on a Large Private &Extensively Landscaped Lot, 4 Bedrooms, Sleeps 9

Modern, spacious recently updated vacation home with a heated pool tucked on 1.5 acres of landscaped grounds provides an ideal setting for families and friends to enjoy their time together. The...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
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: 
$500 per week
Tax: State & Local: 
11.7

Pool Heated to 81 degrees July & August weeks included in the rental rate. 

Pool Heated to 81 degrees,  additional $275 per week June& September weeks 2023

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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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$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
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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
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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
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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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