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 Condo Unit, Gorgeous Water Views, In Town Location, Modern updated Interior!

Note: Seavies 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...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,100 - $3,500
June 2026
SuMoTuWeThFrSaWeek
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$2,150
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$2,150
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$2,550
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$3,500
28
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30
 $3,800
July 2026
SuMoTuWeThFrSaWeek
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$3,800
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$3,900
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$4,600
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$4,600
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30
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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
31
 $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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29
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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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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 - $3,000
June 2026
SuMoTuWeThFrSaWeek
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$2,900
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$2,900
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 $3,000
July 2026
SuMoTuWeThFrSaWeek
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$3,000
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$3,000
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$3,000
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$3,000
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 $3,000
August 2026
SuMoTuWeThFrSaWeek
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$3,000
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$3,000
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$3,000
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$3,000
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$3,000
30
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 $2,900
September 2026
SuMoTuWeThFrSaWeek
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$2,900
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$2,900
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$2,900
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30
 
Clean Fee: 
$360 per week
Tax: State & Local: 
11.7
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KEANM

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Property Details
Lovely Oak Bluffs Home, 3 Bedrooms, 2.5 Baths, Sleeps 7. Set just on the Outskirts of Oak Bluffs Center

Lovely 3 bedroom, 2.5 bath home that sleeps 7. This sweet home is bordered by a large yard and is located just on the outskirts of Oak Bluffs. The patio...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $3,000
June 2026
SuMoTuWeThFrSaWeek
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$3,000
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 $4,600
July 2026
SuMoTuWeThFrSaWeek
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$4,600
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$4,600
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$4,600
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$4,600
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 $4,600
August 2026
SuMoTuWeThFrSaWeek
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$4,600
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$4,700
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$4,700
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$4,700
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$4,700
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 $4,700
September 2026
SuMoTuWeThFrSaWeek
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$4,700
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$3,000
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$3,000
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30
 
Clean Fee: 
$500 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:
$1,900 - $2,700
June 2026
SuMoTuWeThFrSaWeek
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$2,250
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$2,300
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$2,700
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$2,900
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 $3,200
July 2026
SuMoTuWeThFrSaWeek
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$3,200
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$3,200
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$3,200
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$3,200
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 $3,300
August 2026
SuMoTuWeThFrSaWeek
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$3,300
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$3,300
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$3,300
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$3,300
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$2,900
30
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 $2,000
September 2026
SuMoTuWeThFrSaWeek
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$2,000
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$2,000
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$2,000
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$2,000
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29
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 $1,900
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

Cottage books Tuesday to Tuesday July & August weeks

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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 - $2,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
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5
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$2,500
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$2,500
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$2,700
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$2,700
28
29
30
 $3,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
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$3,800
5
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$3,800
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$3,800
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$3,800
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30
31
 $3,800
August 2026
SuMoTuWeThFrSaWeek
 1
$3,800
2
3
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$4,500
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$4,500
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$4,500
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$3,500
30
31
 $3,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$3,000
6
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$2,500
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$2,500
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$2,500
27
28
29
30
 $2,500
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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BROWL

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Property Details
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
SuMoTuWeThFrSa
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July 2026
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August 2026
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September 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

Note: Exterior photos were taken in the winter. The deck will be set up for summer relaxing and dining, not seen in the current photos.  

New Sofas for 2026 in the...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$70 - $70
June 2026
SuMoTuWeThFrSa
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July 2026
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August 2026
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September 2026
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Clean Fee: 
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
SuMoTuWeThFrSa
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July 2026
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August 2026
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September 2026
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29
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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
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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 $5,350
July 2026
SuMoTuWeThFrSaWeek
 1
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$5,350
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$5,350
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$5,350
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$5,350
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 $7,000
August 2026
SuMoTuWeThFrSaWeek
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$7,000
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$7,000
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$7,200
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$7,500
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September 2026
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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MAHAB

(0)Inquire/Share
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
July 2026
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$4,000
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 $4,000
August 2026
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$4,000
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$4,000
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 $4,000
September 2026
SuMoTuWeThFrSaWeek
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$4,000
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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
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
SuMoTuWeThFrSaWeek
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$18,000
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$18,000
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$18,000
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$15,500
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 $15,500
September 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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July 2026
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August 2026
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September 2026
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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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July 2026
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$7,400
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August 2026
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 $5,000
September 2026
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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
SuMoTuWeThFrSaWeek
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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
August 2026
SuMoTuWeThFrSaWeek
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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
SuMoTuWeThFrSaWeek
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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
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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LONAJ

(0)Inquire/Share
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
SuMoTuWeThFrSa
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

 

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