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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Classic Lovely Vineyard Cottage, Approximately 1.5 Miles to Oak Bluffs Center 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:
$2,700 - $4,000
June 2027
SuMoTuWeThFrSaWeek
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$2,700
6
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$2,700
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$2,700
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$2,700
27
28
29
30
 $3,500
July 2027
SuMoTuWeThFrSaWeek
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2
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$3,500
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$3,500
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$3,500
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$3,500
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30
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$4,000
August 2027
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
29
30
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 $3,000
September 2027
SuMoTuWeThFrSaWeek
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$3,000
5
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$2,700
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$2,700
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$2,700
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29
30
 $2,700
Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
14.45
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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 - $3,800
June 2027
SuMoTuWeThFrSaWeek
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$3,800
27
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 $3,800
July 2027
SuMoTuWeThFrSaWeek
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$3,800
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$3,800
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$3,800
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$3,800
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$3,800
August 2027
SuMoTuWeThFrSaWeek
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$3,800
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$3,800
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$3,800
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$3,800
29
30
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 $3,100
September 2027
SuMoTuWeThFrSaWeek
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$3,100
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$2,800
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$2,800
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$2,800
26
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28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
14.45
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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:
$3,500 - $3,500
June 2027
SuMoTuWeThFrSaWeek
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$5,500
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$5,500
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$5,500
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$5,500
27
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29
30
 $6,900
July 2027
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
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$6,900
August 2027
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
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 $6,900
September 2027
SuMoTuWeThFrSaWeek
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$6,900
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$5,500
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$5,200
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$5,200
26
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29
30
 $5,200
Clean Fee: 
$425 per week
Tax: State & Local: 
14.45
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HANRJ~

Inquire
Property Details
Spacious Oak Bluffs Contemporary Home, 4 Bedrooms & 4 Baths, Quiet Private Location in Bayes Hill Community of Homes

Privately situated on the outskirts of Oak Bluffs, yet centrally located to towns and beaches. The home features a large patio area with outdoor dining and grill area and a spacious...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $3,500
June 2027
SuMoTuWeThFrSaWeek
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$3,500
6
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$3,500
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$3,500
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$3,800
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 $4,500
July 2027
SuMoTuWeThFrSaWeek
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$4,500
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$5,500
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$5,500
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$5,500
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$6,000
August 2027
SuMoTuWeThFrSaWeek
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$7,000
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$7,000
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$7,000
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$5,500
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 $4,000
September 2027
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
26
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29
30
 $3,500
Clean Fee: 
$575
Tax: State & Local: 
14.45

 

 

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LODGJ~

Inquire
Property Details
Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet
Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,200 - $3,200
June 2027
SuMoTuWeThFrSaWeek
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$3,200
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$3,200
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 $3,200
July 2027
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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$3,200
August 2027
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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 $3,200
September 2027
SuMoTuWeThFrSaWeek
 1
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$3,200
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$3,200
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$3,200
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29
30
 
Clean Fee: 
$360 per week
Tax: State & Local: 
14.45
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GOLLB~

Inquire
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:
$2,000 - $3,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,250
6
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$2,300
13
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$2,700
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$2,900
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 $3,250
July 2027
SuMoTuWeThFrSaWeek
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2
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$3,250
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$3,250
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$3,250
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$3,250
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$3,350
August 2027
SuMoTuWeThFrSaWeek
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$3,400
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$3,400
15
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$3,400
22
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$3,200
29
30
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 $2,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
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$2,000
5
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$2,000
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$2,000
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$2,000
26
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 $2,000
Clean Fee: 
$325 per week
Tax: State & Local: 
14.45

Cottage books Tuesday to Tuesday July & August weeks

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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 - $2,600
June 2027
SuMoTuWeThFrSaWeek
 1
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3
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5
$3,500
6
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$3,500
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$3,900
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$3,900
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 $6,400
July 2027
SuMoTuWeThFrSaWeek
 1
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$6,400
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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 2027
SuMoTuWeThFrSaWeek
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$7,200
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$7,200
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$7,200
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$7,200
29
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 $7,200
September 2027
SuMoTuWeThFrSaWeek
 1
2
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$7,200
5
6
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$2,700
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$2,700
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$2,700
26
27
28
29
30
 $2,700
Clean Fee: 
$425 per week
Tax: State & Local: 
14.45

Owner books Fri to Fri 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 2027
SuMoTuWeThFrSa
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July 2027
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August 2027
SuMoTuWeThFrSaWeek
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$15,000
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$15,000
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September 2027
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Clean Fee: 
$550
Tax: State & Local: 
14.45
Add Favorite
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BURBS~

Inquire
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:
$0 - $0
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSaWeek
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$6,500
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$6,500
August 2027
SuMoTuWeThFrSaWeek
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$7,100
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$7,100
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September 2027
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Clean Fee: 
$475 per week
Tax: State & Local: 
14.45
Add Favorite
 
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ST203

Inquire
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: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$0 - $0
June 2027
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July 2027
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September 2027
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Clean Fee: 
$275 per week
Tax: State & Local: 
14.45
Add Favorite
 
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ST304

Inquire
Property Details
Sea View Condominium, Water View, Walk to Town & Beach-Across the Street

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
June 2027
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July 2027
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September 2027
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Clean Fee: 
$275 per week
Tax: State & Local: 
14.45
Add Favorite
 
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ALLER

Inquire
Property Details
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 2027
SuMoTuWeThFrSaWeek
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$3,680
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$3,680
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$3,680
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$3,900
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29
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 $5,250
July 2027
SuMoTuWeThFrSaWeek
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$5,250
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$5,250
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$5,250
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$5,250
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$5,250
August 2027
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
22
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$5,750
29
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 $4,500
September 2027
SuMoTuWeThFrSaWeek
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$4,500
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$4,200
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$4,200
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$4,200
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 $4,200
Clean Fee: 
$475 per week
Tax: State & Local: 
14.45
Add Favorite
 
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KLEIB

Inquire
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
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$250 per week
Tax: State & Local: 
14.45
Add Favorite
 
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CENCR

Inquire
Property Details
Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Great Area for Kayaking.

Spacious sun-filled home features open living spaces, hardwood floors throughout, 4 bedrooms and sleeps 8.

Exterior features include two decks, one sunny deck at the front of the house, and a large private...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$480 per week
Tax: State & Local: 
14.45
Add Favorite
 
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LIJOY~

Inquire
Property Details
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:
$0 - $0
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
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 $6,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,800
4
5
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$7,200
11
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$7,000
18
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$7,000
25
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$7,300
August 2027
SuMoTuWeThFrSaWeek
1
2
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$7,300
8
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$7,800
15
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$7,800
22
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$7,300
29
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 $6,800
September 2027
SuMoTuWeThFrSaWeek
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2
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$6,800
5
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$7,000
12
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Clean Fee: 
$420 per week
Tax: State & Local: 
14.45

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