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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Chic, Meticulously Maintained Cape Style Home. Walk to Oak Bluffs Town Center and Beaches, Tucked on a Large Beautifully Landscaped Lot

Nestled in a beautifully landscaped lot in a serene and private neighborhood, this meticulously maintained cottage in Oak Bluffs, Martha's Vineyard, offers a perfect retreat for rental guests. With chic...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
3
Price Range:
$3,750 - $6,350
June 2025
SuMoTuWeThFrSaWeek
1
2
3
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5
6
7
$3,750
8
9
10
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12
13
14
$3,750
15
16
17
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21
$4,350
22
23
24
25
26
27
28
$4,600
29
30
 $5,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
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10
11
12
$5,000
13
14
15
16
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18
19
$5,600
20
21
22
23
24
25
26
$5,600
27
28
29
30
31
 $5,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,600
3
4
5
6
7
8
9
$6,350
10
11
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$6,350
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$6,350
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25
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27
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29
30
$6,350
31
 $3,750
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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5
6
$3,750
7
8
9
10
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13
$3,750
14
15
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$3,750
21
22
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24
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26
27
$3,750
28
29
30
 $3,750
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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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:
$3,850 - $6,090
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,850
8
9
10
11
12
13
14
$3,850
15
16
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18
19
20
21
$4,960
22
23
24
25
26
27
28
$4,960
29
30
 $6,090
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,090
6
7
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10
11
12
$6,090
13
14
15
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19
$6,090
20
21
22
23
24
25
26
$6,090
27
28
29
30
31
 $6,090
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,090
3
4
5
6
7
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$6,090
10
11
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13
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$6,090
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18
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20
21
22
23
$6,090
24
25
26
27
28
29
30
$6,090
31
 $6,090
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,090
7
8
9
10
11
12
13
$4,960
14
15
16
17
18
19
20
$3,850
21
22
23
24
25
26
27
$3,850
28
29
30
 $3,850
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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DAWKN

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Property Details
Exquisite Designer Home, 10 minute Walk to Oak Bluffs Town Center, Screened Porch, Patio Dining Area, Landscaped Yard, Professionally Decorated, AC

Quietly nestled on a quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,050 - $6,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,300
8
9
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13
14
$5,300
15
16
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21
$5,300
22
23
24
25
26
27
28
$5,400
29
30
 $6,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
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12
$6,000
13
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$6,000
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21
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$6,000
27
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30
31
 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,000
3
4
5
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$6,000
10
11
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$6,000
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18
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21
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$6,000
24
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27
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29
30
$6,000
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
 1
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3
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5
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$6,000
7
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$5,100
14
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20
$5,100
21
22
23
24
25
26
27
$5,100
28
29
30
 $5,100
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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HANRJ

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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 - $6,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,300
8
9
10
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13
14
$4,300
15
16
17
18
19
20
21
$4,300
22
23
24
25
26
27
28
$4,500
29
30
 $5,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
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10
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12
$5,000
13
14
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$6,000
20
21
22
23
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25
26
$6,000
27
28
29
30
31
 $5,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,500
3
4
5
6
7
8
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$7,000
10
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$7,000
17
18
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21
22
23
$7,000
24
25
26
27
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29
30
$5,500
31
 $5,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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6
$5,000
7
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13
$4,000
14
15
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20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 $3,500
Clean Fee: 
$575
Tax: State & Local: 
11.7

 

 

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BOOND

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Property Details
Wonderful Vacation Home, East Chop Area of Oak Bluffs, Private Yard, Screened Porch, 4 bedrooms, 2 baths.

Nestled on a quiet street in the idyllic East Chop area of Oak Bluffs, this classic New England summer home offers vacationing families and friends a special place to gather...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,200 - $6,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,200
8
9
10
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13
14
$4,200
15
16
17
18
19
20
21
$4,200
22
23
24
25
26
27
28
$4,200
29
30
 $5,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,200
6
7
8
9
10
11
12
$5,200
13
14
15
16
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18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
31
 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,000
3
4
5
6
7
8
9
$6,000
10
11
12
13
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$6,500
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18
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20
21
22
23
$6,500
24
25
26
27
28
29
30
$6,000
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
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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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 - $5,900
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,800
8
9
10
11
12
13
14
$3,800
15
16
17
18
19
20
21
$3,800
22
23
24
25
26
27
28
$5,100
29
30
 $6,100
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,100
6
7
8
9
10
11
12
$6,100
13
14
15
16
17
18
19
$6,100
20
21
22
23
24
25
26
$6,300
27
28
29
30
31
 $6,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,600
3
4
5
6
7
8
9
$6,600
10
11
12
13
14
15
16
$6,600
17
18
19
20
21
22
23
$6,600
24
25
26
27
28
29
30
$5,900
31
 $3,800
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,800
7
8
9
10
11
12
13
$3,800
14
15
16
17
18
19
20
$3,800
21
22
23
24
25
26
27
$3,800
28
29
30
 $2,700
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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THOMS

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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 - $5,820
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,800
8
9
10
11
12
13
14
$3,800
15
16
17
18
19
20
21
$3,800
22
23
24
25
26
27
28
$5,500
29
30
 $6,300
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,300
6
7
8
9
10
11
12
$6,300
13
14
15
16
17
18
19
$6,300
20
21
22
23
24
25
26
$6,300
27
28
29
30
31
 $6,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,800
3
4
5
6
7
8
9
$6,800
10
11
12
13
14
15
16
$6,800
17
18
19
20
21
22
23
$6,800
24
25
26
27
28
29
30
$6,800
31
 $5,820
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,820
7
8
9
10
11
12
13
$3,800
14
15
16
17
18
19
20
$3,800
21
22
23
24
25
26
27
$3,800
28
29
30
 $3,800
Clean Fee: 
$425 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:
$3,700 - $5,750
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,700
8
9
10
11
12
13
14
$3,700
15
16
17
18
19
20
21
$3,700
22
23
24
25
26
27
28
$3,900
29
30
 $5,250
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,250
6
7
8
9
10
11
12
$5,250
13
14
15
16
17
18
19
$5,250
20
21
22
23
24
25
26
$5,250
27
28
29
30
31
 $5,250
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,250
3
4
5
6
7
8
9
$6,000
10
11
12
13
14
15
16
$6,000
17
18
19
20
21
22
23
$6,000
24
25
26
27
28
29
30
$5,750
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,200
14
15
16
17
18
19
20
$4,200
21
22
23
24
25
26
27
$4,200
28
29
30
 
Clean Fee: 
$475 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:
$5,500 - $5,500
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
31
 $6,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,000
3
4
5
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September 2025
SuMoTuWeThFrSa
 1
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12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Transferrable Ferry Tickets available, 7/13 -7/20 & 7/20 -7/27. Please inquire for details!

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ROS22

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Property Details

Set in the heart of Oak Bluffs and on a quiet residential street, this newly updated tastefully decorated vacation home offers rental guests all the comforts of home inside and out....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $5,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,000
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $5,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$5,000
13
14
15
16
17
18
19
$5,000
20
21
22
23
24
25
26
$5,000
27
28
29
30
31
 $5,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,500
3
4
5
6
7
8
9
$5,500
10
11
12
13
14
15
16
$5,500
17
18
19
20
21
22
23
$5,500
24
25
26
27
28
29
30
$5,500
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$4,000
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 $3,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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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 - $5,300
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,320
8
9
10
11
12
13
14
$3,320
15
16
17
18
19
20
21
$3,500
22
23
24
25
26
27
28
$3,600
29
30
 $4,600
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,600
6
7
8
9
10
11
12
$4,800
13
14
15
16
17
18
19
$4,800
20
21
22
23
24
25
26
$4,800
27
28
29
30
31
 $5,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,200
3
4
5
6
7
8
9
$5,300
10
11
12
13
14
15
16
$5,300
17
18
19
20
21
22
23
$5,600
24
25
26
27
28
29
30
$5,300
31
 $3,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,600
7
8
9
10
11
12
13
$3,300
14
15
16
17
18
19
20
$2,900
21
22
23
24
25
26
27
$2,900
28
29
30
 $2,900
Clean Fee: 
$275 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 - $5,300
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,320
8
9
10
11
12
13
14
$3,320
15
16
17
18
19
20
21
$3,500
22
23
24
25
26
27
28
$3,600
29
30
 $4,600
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,600
6
7
8
9
10
11
12
$4,800
13
14
15
16
17
18
19
$4,800
20
21
22
23
24
25
26
$4,800
27
28
29
30
31
 $4,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,800
3
4
5
6
7
8
9
$5,300
10
11
12
13
14
15
16
$5,300
17
18
19
20
21
22
23
$5,600
24
25
26
27
28
29
30
$5,300
31
 $3,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,600
7
8
9
10
11
12
13
$3,300
14
15
16
17
18
19
20
$2,900
21
22
23
24
25
26
27
$2,900
28
29
30
 $2,900
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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PEOTA

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Property Details
Pristine Water view Home, Located in the Community of Homes known as Water View Farms, Walk to Private Association Waterfront, Great Play Beach, Launch Kayaks

This charming updated home is set in idyllic Water View Farms overlooking Sengekontacket pond.  This well-thought-out home offers a beautifully landscaped yard and cottage-style living with indoor spaces that transition...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,000 - $5,250
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$3,500
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,720
29
30
 $5,250
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,250
6
7
8
9
10
11
12
$5,250
13
14
15
16
17
18
19
$5,250
20
21
22
23
24
25
26
$5,250
27
28
29
30
31
 $5,770
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,770
3
4
5
6
7
8
9
$5,770
10
11
12
13
14
15
16
$5,770
17
18
19
20
21
22
23
$5,770
24
25
26
27
28
29
30
$4,720
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,000
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$2,500
28
29
30
 $2,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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DENAL

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Property Details

Charming, 4-bedroom Oak Bluffs Home, pristinely maintained!  The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,000 - $5,250
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,500
8
9
10
11
12
13
14
$2,500
15
16
17
18
19
20
21
$2,500
22
23
24
25
26
27
28
$2,500
29
30
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
31
 $3,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,000
3
4
5
6
7
8
9
$5,000
10
11
12
13
14
15
16
$5,750
17
18
19
20
21
22
23
$5,750
24
25
26
27
28
29
30
$5,250
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$2,000
14
15
16
17
18
19
20
$2,000
21
22
23
24
25
26
27
$2,000
28
29
30
 $2,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Parking for two cars only, no on-street parking!

 

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DHANM

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Property Details
Adorable Oak Bluffs Cottage Just Over a Mile to the Village Center and Town Beaches, Porch, Deck, 4 Bedrooms, 2 Baths

Nestled on a quiet street, this recently updated residence boasts delightful indoor and outdoor living areas. The entrance porch offers cozy seating with wicker chairs and a small dining table that...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,300 - $5,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$3,600
29
30
 $4,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,200
6
7
8
9
10
11
12
$4,200
13
14
15
16
17
18
19
$4,200
20
21
22
23
24
25
26
$4,200
27
28
29
30
31
 $4,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,200
3
4
5
6
7
8
9
$5,000
10
11
12
13
14
15
16
$5,700
17
18
19
20
21
22
23
$5,000
24
25
26
27
28
29
30
$5,000
31
 $4,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,900
7
8
9
10
11
12
13
$3,000
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$3,000
28
29
30
 $2,300
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

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