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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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:
$10 - $2,500
June 2025
SuMoTuWeThFrSaWeek
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$2,500
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$2,500
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$2,500
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$3,300
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 $3,300
July 2025
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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 $3,300
August 2025
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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$3,000
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 $2,500
September 2025
SuMoTuWeThFrSaWeek
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$2,500
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$2,500
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$2,500
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$2,500
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30
 $2,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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ADELM

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Property Details
Waterfront Lagoon, Deck with Gorgeous Sunset Views, WiFi

Adorable waterfront cottage, pristinely maintained throughout the years.  Enjoy privacy and and gorgeous water views of the lagoon from the spacious deck.  Wade across the generally ankle deep inlet in...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
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$1,900
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$1,900
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$2,280
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$2,850
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 $2,850
July 2025
SuMoTuWeThFrSaWeek
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$2,850
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$2,850
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$2,850
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$2,850
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 $3,050
August 2025
SuMoTuWeThFrSaWeek
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$3,050
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$3,050
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$3,050
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$3,050
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$2,270
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 $1,950
September 2025
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$1,950
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$1,950
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$1,950
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30
 $1,950
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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ST203

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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: 
5
Bedrooms: 
2
Baths: 
2
Price Range:
$10 - $10
June 2025
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August 2025
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September 2025
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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:
$10 - $10
June 2025
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July 2025
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September 2025
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Clean Fee: 
$199 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:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
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$6,050
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 $5,800
July 2025
SuMoTuWeThFrSaWeek
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$5,800
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$5,800
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$5,800
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$6,050
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 $6,500
August 2025
SuMoTuWeThFrSaWeek
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$6,500
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$6,500
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$6,500
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September 2025
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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LONGK

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Property Details
Bayes Hill Beauty - Central A/C, Wifi, Association Tennis, Bose Soundock II
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
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$2,750
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$2,750
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$3,000
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$3,000
29
30
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
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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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 $4,000
August 2025
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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$3,750
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 $3,250
September 2025
SuMoTuWeThFrSaWeek
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$3,250
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$3,000
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$3,000
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$2,500
28
29
30
 $2,500
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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ALLER

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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:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
1
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3
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7
$3,700
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$3,700
15
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$3,700
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$3,700
29
30
 $4,900
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$4,900
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$4,900
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$4,900
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$4,900
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31
 $4,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,900
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$6,000
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$6,000
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$6,000
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$5,200
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 $4,200
September 2025
SuMoTuWeThFrSaWeek
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$4,200
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$4,200
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$4,200
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$4,200
28
29
30
 
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
Add Favorite
rolaj13-01-patio.jpg
 
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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:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,300
8
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14
$4,300
15
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$5,100
22
23
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27
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$6,000
29
30
 $6,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$6,200
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$6,200
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$6,200
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$6,200
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 $6,300
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,300
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$6,300
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$6,300
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$6,300
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$5,800
31
 $5,900
September 2025
SuMoTuWeThFrSaWeek
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$5,900
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$5,900
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$5,900
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$5,900
28
29
30
 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ROCHA

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Property Details
Bridle Path House, Quiet Lovely Neighborhood, Porch and Deck Areas, Large Yard, Central Location to all 3 Down Island Towns and Beaches

Lovely 3 bedroom 3 bath home bordered by a large landscaped yard. The exterior features a shady wrap-around porch with rockers, a perfect place to relax, read a book and enjoy the...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
1
2
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14
$5,100
15
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$5,100
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$5,900
29
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 $5,900
July 2025
SuMoTuWeThFrSaWeek
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$5,900
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$5,900
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$5,900
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$5,900
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 $5,900
August 2025
SuMoTuWeThFrSaWeek
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$5,900
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$5,900
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$5,900
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$5,900
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$5,900
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September 2025
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Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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COONC

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Property Details
The Boathouse, East Chop Location, Gorgeous Water and Sunset Views, Architect Designed Gem

Designed by a renowned island architect and custom-crafted,  The Boathouse underwent construction and total renovation in 2016 and is now a terrific year-round home.  The exterior of the house maintains...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
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$6,500
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$6,500
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$6,500
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$6,500
29
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 $8,000
July 2025
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
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$8,000
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$8,000
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 $8,000
August 2025
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
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$8,000
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$8,000
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$8,000
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 $8,000
September 2025
SuMoTuWeThFrSaWeek
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$8,000
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$6,500
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$6,500
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$6,500
28
29
30
 $4,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Two-week minimum stay per owner! 

 

 

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SUTTJ

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Property Details
Newly Renovated, Modern Cottage Luxury, Professionally Decorated, 1 mile from Oak Bluffs Center & Beach

Stunning new stylish renovation, professionally decorated, a step above your average rental, and just 1 mile to the Harbor and the center of Oak Bluffs!

The main living level features an...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
1
2
3
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5
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7
$3,000
8
9
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13
14
$3,500
15
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$3,800
22
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27
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$4,950
29
30
 $5,800
July 2025
SuMoTuWeThFrSaWeek
 1
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3
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$5,800
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$5,800
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$5,800
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$6,000
27
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31
 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,000
3
4
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$6,000
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$6,500
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$6,500
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25
26
27
28
29
30
$6,000
31
 $4,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,600
7
8
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10
11
12
13
$3,500
14
15
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20
$3,500
21
22
23
24
25
26
27
$3,500
28
29
30
 $2,900
Clean Fee: 
$500 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:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
1
2
3
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$7,500
8
9
10
11
12
13
14
$7,500
15
16
17
18
19
20
21
$7,500
22
23
24
25
26
27
28
$7,500
29
30
 $7,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$9,250
20
21
22
23
24
25
26
$9,250
27
28
29
30
31
 $9,250
August 2025
SuMoTuWeThFrSaWeek
 1
2
$9,250
3
4
5
6
7
8
9
$12,250
10
11
12
13
14
15
16
$12,250
17
18
19
20
21
22
23
$12,250
24
25
26
27
28
29
30
$7,500
31
 $7,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,500
7
8
9
10
11
12
13
14
15
16
17
18
19
20
$6,250
21
22
23
24
25
26
27
$6,250
28
29
30
 $6,250
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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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:
$10 - $10
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,000
8
9
10
11
12
13
14
$5,000
15
16
17
18
19
20
21
$5,000
22
23
24
25
26
27
28
$5,000
29
30
 $9,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,200
6
7
8
9
10
11
12
$9,200
13
14
15
16
17
18
19
$9,200
20
21
22
23
24
25
26
$9,200
27
28
29
30
31
 $9,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$9,200
3
4
5
6
7
8
9
$9,200
10
11
12
13
14
15
16
$9,200
17
18
19
20
21
22
23
$9,200
24
25
26
27
28
29
30
$6,900
31
 $6,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,900
7
8
9
10
11
12
13
$5,000
14
15
16
17
18
19
20
$5,000
21
22
23
24
25
26
27
$5,000
28
29
30
 $5,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

 

 

 

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