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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Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, Bike Paths at Entrance to Neighborhood, Multiple Beaches Near By

Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,700 - $7,800
June 2026
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July 2026
SuMoTuWeThFrSaWeek
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$6,400
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$6,400
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$6,400
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 $6,600
August 2026
SuMoTuWeThFrSaWeek
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$6,600
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$7,000
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$7,000
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$7,000
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$6,400
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 $6,700
September 2026
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$6,700
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$5,500
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$4,700
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$4,700
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 $4,700
Clean Fee: 
$420 per week
Tax: State & Local: 
11.7
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INGAE

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Property Details
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$5,250 - $7,750
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$9,750
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$9,750
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$9,750
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 $11,000
August 2026
SuMoTuWeThFrSaWeek
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$11,000
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$11,000
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$11,000
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$11,000
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$11,000
30
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 $7,750
September 2026
SuMoTuWeThFrSaWeek
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$7,750
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$7,000
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$6,900
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$6,800
27
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29
30
 $6,700
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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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:
$5,500 - $7,500
June 2026
SuMoTuWeThFrSa
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July 2026
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$5,500
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$5,000
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$5,000
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August 2026
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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$7,500
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September 2026
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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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:
$3,500 - $7,500
June 2026
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July 2026
SuMoTuWeThFrSaWeek
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$5,000
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$4,000
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$4,000
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 $5,000
August 2026
SuMoTuWeThFrSaWeek
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$5,000
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$7,500
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$7,500
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$7,500
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$5,000
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 $4,500
September 2026
SuMoTuWeThFrSaWeek
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$4,500
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$4,500
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$3,500
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$3,500
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 $3,500
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Rates reduced for available weeks June - July - see calendar for adjusted rates

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WHARG

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Property Details
Lovely Home in a quiet Neighborhood. Walk to Town Center and Inkwell Beach, Large Private Deck, Room AC

Spacious sun-filled contemporary home located on a quiet private street, a 10-minute walk to town center, Inkwell Beach, and the harborfront.

The first level features a spacious kitchen with stainless steel...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$7,200 - $7,200
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$6,900
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$6,900
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$6,900
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 $6,900
August 2026
SuMoTuWeThFrSaWeek
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$6,900
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$7,900
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$7,900
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$7,900
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$7,900
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 $7,200
September 2026
SuMoTuWeThFrSaWeek
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$7,200
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Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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ROBIH

Inquire
Property Details
Seaview Condo Unit, Gorgeous Water Views, In Town Location, Modern updated Interior!

Note: Seaview Condos is a 3-minute walk from the Steamship Authority dock in Oak Bluffs and two blocks from the Island Queen ferry dock. Perfect location if you cannot or do...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,100 - $7,200
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$3,900
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$4,600
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$4,600
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 $5,600
August 2026
SuMoTuWeThFrSaWeek
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$5,600
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$5,600
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$5,600
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$5,600
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$3,900
30
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 $2,500
September 2026
SuMoTuWeThFrSaWeek
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$2,500
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$2,500
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$2,100
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$2,100
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 $2,100
Clean Fee: 
$240 per week
Tax: State & Local: 
11.7

5 minute walk from Steamship Authority Oak Bluffs dock to the Seaview Condos.  2 blocks from the Island Queen ferry dock.  

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TERSM

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Property Details
Modern, Newly Renovated, Architecturally Significant Beach Cottage Design. Close to Town and Beaches, Tucked in the Lovely Community of Summer Homes, Waterview Farms!

Gorgeous all newly renovated and newly furnished mid-century beach cottage, now a modern vacation oasis designed by the prominent interior design firm, - Tersigni Palachek. This eloquent, yet beachy home offers...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,600 - $7,200
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$6,400
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$6,400
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$6,400
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 $6,400
August 2026
SuMoTuWeThFrSaWeek
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$6,400
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$7,200
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$7,200
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$7,200
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$7,200
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 $7,200
September 2026
SuMoTuWeThFrSaWeek
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$7,200
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$2,700
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$2,700
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$2,700
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 $2,700
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Owner books Fri to Fri July & August weeks!

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BICKE

Inquire
Property Details
East Chop Area, Tri-Level Home with Distant Water views, Located just 1.5 Mi to Oak Bluffs Center

East Chop Escape with lovely Distant Water Views
Light-Filled Tri-Level Home, 4 Bedrooms, & 3 baths, 1.5 Miles to Oak Bluffs Center

Set in the highly sought-after East Chop neighborhood,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $7,150
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$7,150
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$7,150
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$7,150
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 $7,150
August 2026
SuMoTuWeThFrSaWeek
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$7,150
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$7,150
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$7,150
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$7,150
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$7,150
30
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 $7,000
September 2026
SuMoTuWeThFrSaWeek
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$7,000
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$6,500
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$6,500
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$6,500
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 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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BURBS

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Property Details
Set Just on the ouskirts of Oak Bluffs. Central AC, Screened Porch

Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs center and beach area.  Fully furnished screen porch and shady porch.  This lovely home sleeps families of 8 comfortably.

The main...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$6,500 - $7,100
June 2026
SuMoTuWeThFrSa
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July 2026
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$6,000
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 $6,500
August 2026
SuMoTuWeThFrSaWeek
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$6,500
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$7,000
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$6,500
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 $6,500
September 2026
SuMoTuWeThFrSaWeek
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$6,500
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Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
Add Favorite
 
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JOSEJ

Inquire
Property Details
Exquisite Coastal Style Home, Pool, Patio, Landscaped Yard! 10 minute walk to Oak Bluffs Center, Luxury Interior, 3 bedrooms, 4 baths, Multiple Living Spaces

This newly constructed, luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with varying depths of 3 to 8 feet, a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $7,000
June 2026
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July 2026
SuMoTuWeThFrSaWeek
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$11,500
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$11,500
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$11,500
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 $11,500
August 2026
SuMoTuWeThFrSaWeek
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$11,500
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$13,000
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$13,000
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$13,000
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$11,500
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 $11,500
September 2026
SuMoTuWeThFrSaWeek
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$11,500
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$7,000
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$6,000
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$6,000
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 $6,500
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Pool Heated to  81 degrees included in rental rate last Sat in June to first Sat in September. Pool Depth 3 feet to 8 Feet 

Pool Heated to 81 degrees June and September weeks additional $275 per week  

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DONAK

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Property Details
Stunning Luxury Home, Complete Renovation in Main House, Sweet Updated Guest House, Walk to Oak Bluffs Center

Gorgeous Luxury Home, Newly Renovated with Stylish Updates, Walking Distance to Oak Bluffs Center

This stunning bungalow-style home has undergone a complete renovation, blending luxury designer decor with the original...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$7,000 - $7,000
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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 $15,000
August 2026
SuMoTuWeThFrSaWeek
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$15,000
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$17,000
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$17,000
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$12,000
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$10,000
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 $7,000
September 2026
SuMoTuWeThFrSaWeek
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$7,000
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$7,000
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$7,000
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$7,000
27
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
Add Favorite
 
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THOMS

Inquire
Property Details
New Modern Farmhouse Design, Great Location!, Wraparound Farmers Porch, Deck Area.

Beautiful new 4 bedroom home, 3.5 bath sleeps 8.  Ideally located just 2 miles from the center of Oak Bluffs and just minutes by car to the towns of Vineyard Haven and...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,100 - $6,900
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$6,400
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13
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$6,400
19
20
21
22
23
24
25
$6,400
26
27
28
29
30
31
 $6,900
August 2026
SuMoTuWeThFrSaWeek
 1
$6,900
2
3
4
5
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$6,800
9
10
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$6,800
16
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$6,800
23
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$6,800
30
31
 $6,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,900
6
7
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10
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$3,800
13
14
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$3,800
20
21
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$3,800
27
28
29
30
 $3,800
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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FISHJ

Inquire
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:
$3,500 - $6,900
June 2026
SuMoTuWeThFrSa
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2
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July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$6,900
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$6,900
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$6,900
26
27
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30
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 $6,900
August 2026
SuMoTuWeThFrSaWeek
 1
$6,900
2
3
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5
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$6,900
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10
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$6,900
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$6,900
23
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$6,900
30
31
 $6,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,900
6
7
8
9
10
11
12
$5,500
13
14
15
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$4,500
20
21
22
23
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$4,500
27
28
29
30
 $4,500
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
Add Favorite
 
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HOD28

Inquire
Property Details
Beautiful Oak Bluffs home just blocks from the Center of Town, Ocean Park and Inkwell Beach.

Note: the kitchen is being completely remodeled for summer 2024 and will have all new high-end appliances, Subzero, Thermador, and new cabinets, and counters. 

Summer Joy!  Set in the heart of...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$5,750 - $6,750
June 2026
SuMoTuWeThFrSa
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2
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27
28
29
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July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
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9
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$8,250
12
13
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18
$8,250
19
20
21
22
23
24
25
$8,250
26
27
28
29
30
31
 $8,250
August 2026
SuMoTuWeThFrSaWeek
 1
$8,250
2
3
4
5
6
7
8
$9,000
9
10
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14
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$9,000
16
17
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$9,000
23
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$9,000
30
31
 $6,750
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,750
6
7
8
9
10
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12
$6,750
13
14
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18
19
$6,750
20
21
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23
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25
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$6,750
27
28
29
30
 $5,750
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

8-minute walk from the ferry dock in Oak Bluffs and 5 minute walk to the Ink Well Beach, and Oak Bluffs Center from the house. 

Add Favorite
 
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ARMSA

Inquire
Property Details
Cozy Newly updated Seashore Cottage, East Chop Highlands Area, Farmers Porch and Deck

If you are looking for an immaculate, charming, cottage-style, yet modern home close to Oak Bluffs center, look no further. This recently updated 3 bedroom, 2 bath home features sunny open...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,600 - $6,700
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
 1
2
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$6,700
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$6,700
19
20
21
22
23
24
25
$6,700
26
27
28
29
30
31
 $6,700
August 2026
SuMoTuWeThFrSaWeek
 1
$6,700
2
3
4
5
6
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$6,700
9
10
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$6,700
16
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$6,700
23
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28
29
$6,700
30
31
 $5,600
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,600
6
7
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$5,600
13
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19
$5,600
20
21
22
23
24
25
26
$5,600
27
28
29
30
 $5,600
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

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