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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Waterview, Walk to the Beach and Town Center, Impeccably Maintained 4 bedroom Home set in the Heart of Oak Bluffs.
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10 - $12,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,400
8
9
10
11
12
13
14
$4,400
15
16
17
18
19
20
21
$4,900
22
23
24
25
26
27
28
$4,900
29
30
 $9,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,000
6
7
8
9
10
11
12
$9,000
13
14
15
16
17
18
19
$9,000
20
21
22
23
24
25
26
$9,000
27
28
29
30
31
 $12,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$12,000
3
4
5
6
7
8
9
$12,000
10
11
12
13
14
15
16
$12,000
17
18
19
20
21
22
23
$12,000
24
25
26
27
28
29
30
$8,500
31
 $5,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,700
7
8
9
10
11
12
13
$5,700
14
15
16
17
18
19
20
$5,700
21
22
23
24
25
26
27
$5,700
28
29
30
 $5,600
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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CENCR

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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:
$10 - $11,800
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,800
22
23
24
25
26
27
28
$4,800
29
30
 $6,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,800
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
31
 $7,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,500
3
4
5
6
7
8
9
$11,800
10
11
12
13
14
15
16
$11,800
17
18
19
20
21
22
23
$11,800
24
25
26
27
28
29
30
$5,800
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
$3,500
21
22
23
24
25
26
27
$3,000
28
29
30
 $3,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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PIN15

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Property Details
Beautiful Oak Bluffs Home, Screened Porch & Open Porch, Association Tennis Courts, 4 bedrooms, 3.5 baths, Ideally Located just 2 miles to Town and Beach

Spacious contemporary home nestled in the lovely community of homes Meadow View Farms just on the outskirts of Oak Bluffs and 2 miles to town center and Oak Bluffs beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10 - $11,750
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,750
8
9
10
11
12
13
14
$9,750
15
16
17
18
19
20
21
$9,750
22
23
24
25
26
27
28
$9,750
29
30
 $11,750
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,750
6
7
8
9
10
11
12
$11,750
13
14
15
16
17
18
19
$11,750
20
21
22
23
24
25
26
$11,750
27
28
29
30
31
 $11,750
August 2025
SuMoTuWeThFrSaWeek
 1
2
$11,750
3
4
5
6
7
8
9
$11,750
10
11
12
13
14
15
16
$11,750
17
18
19
20
21
22
23
$11,750
24
25
26
27
28
29
30
$11,750
31
 $11,750
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$11,750
7
8
9
10
11
12
13
$9,750
14
15
16
17
18
19
20
$9,750
21
22
23
24
25
26
27
$9,750
28
29
30
 $6,820
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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HOL14

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Property Details
Gorgeous Waterfront Home on the Lagoon Oak Bluffs, Kayak, Swim, Enjoy the Sunsets, 4 bedrooms 4.5 Baths

Stunning Waterfront home nestled just in the outskirts of Oak Bluffs, 1 mile from town center and Oak Bluffs beaches. This home offers 150 feet of private lagoon beach perfect...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$10 - $11,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,000
8
9
10
11
12
13
14
$9,000
15
16
17
18
19
20
21
$9,000
22
23
24
25
26
27
28
$9,000
29
30
 $11,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,500
6
7
8
9
10
11
12
$11,500
13
14
15
16
17
18
19
$11,500
20
21
22
23
24
25
26
$11,500
27
28
29
30
31
 $15,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$15,800
3
4
5
6
7
8
9
$15,800
10
11
12
13
14
15
16
$15,800
17
18
19
20
21
22
23
$15,800
24
25
26
27
28
29
30
$15,800
31
 $9,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$9,500
7
8
9
10
11
12
13
$9,000
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$7,000
28
29
30
 $7,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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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:
$10 - $11,500
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
 $7,400
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,400
6
7
8
9
10
11
12
$7,400
13
14
15
16
17
18
19
$7,400
20
21
22
23
24
25
26
$7,400
27
28
29
30
31
 $8,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,500
3
4
5
6
7
8
9
$10,500
10
11
12
13
14
15
16
$10,500
17
18
19
20
21
22
23
$11,500
24
25
26
27
28
29
30
$8,500
31
 $5,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$450 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:
$10 - $11,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,750
8
9
10
11
12
13
14
$5,750
15
16
17
18
19
20
21
$5,750
22
23
24
25
26
27
28
$7,000
29
30
 $9,750
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,750
6
7
8
9
10
11
12
$9,750
13
14
15
16
17
18
19
$9,750
20
21
22
23
24
25
26
$9,750
27
28
29
30
31
 $11,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$11,000
3
4
5
6
7
8
9
$11,000
10
11
12
13
14
15
16
$11,000
17
18
19
20
21
22
23
$11,000
24
25
26
27
28
29
30
$11,000
31
 $7,750
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,750
7
8
9
10
11
12
13
$7,000
14
15
16
17
18
19
20
$6,900
21
22
23
24
25
26
27
$6,800
28
29
30
 $6,700
Clean Fee: 
$500 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:
$10 - $11,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$10,000
8
9
10
11
12
13
14
$10,000
15
16
17
18
19
20
21
$10,000
22
23
24
25
26
27
28
$10,000
29
30
 $10,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$10,000
20
21
22
23
24
25
26
$10,000
27
28
29
30
31
 $10,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$10,000
3
4
5
6
7
8
9
$11,000
10
11
12
13
14
15
16
$11,000
17
18
19
20
21
22
23
$11,000
24
25
26
27
28
29
30
$11,000
31
 $10,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$10,000
7
8
9
10
11
12
13
$10,000
14
15
16
17
18
19
20
$10,000
21
22
23
24
25
26
27
$10,000
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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GOLDF

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Property Details
Outstanding Oak Bluffs Summer Home with Heated Pool and Patio Surround, Screened Porch with Living and Dining Area, Association Tennis Courts.

MVVR Exclusive Listing:  Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful getaway yet is just a short drive to the...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$10 - $10,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
$9,000
29
30
 $10,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$10,500
20
21
22
23
24
25
26
$10,500
27
28
29
30
31
 $11,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$11,000
3
4
5
6
7
8
9
$11,000
10
11
12
13
14
15
16
$11,000
17
18
19
20
21
22
23
$11,000
24
25
26
27
28
29
30
$9,000
31
 $9,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$9,000
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$5,500
21
22
23
24
25
26
27
$5,500
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Pool Heated to 80 July & August and the 1st week in September included in the rental rate!

 

Pool Heated to 80  May, June & September weeks at additional cost ($400). 

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ROSKH

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Property Details
East Chop Classic Waterfront Home, Private Dock, Mooring Available, Spectacular Sunsets

Experience the epitome of summer living at East Chop Oak Bluffs in this delightful waterfront retreat. Nestled amidst the serenity of the beachfront, this cozy home boasts a private dock...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $10,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,000
8
9
10
11
12
13
14
$6,000
15
16
17
18
19
20
21
$6,000
22
23
24
25
26
27
28
$6,000
29
30
 $10,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$10,000
20
21
22
23
24
25
26
$10,000
27
28
29
30
31
 $10,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$10,000
3
4
5
6
7
8
9
$10,000
10
11
12
13
14
15
16
$10,000
17
18
19
20
21
22
23
$10,000
24
25
26
27
28
29
30
$10,000
31
 $8,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$6,000
28
29
30
 $6,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
Add Favorite
 
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CURRM

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Property Details
Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

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

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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POWDA

(0)Inquire/Share
Property Details
Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$10 - $9,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,000
8
9
10
11
12
13
14
$6,500
15
16
17
18
19
20
21
$7,000
22
23
24
25
26
27
28
$7,500
29
30
 $8,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,500
6
7
8
9
10
11
12
$8,500
13
14
15
16
17
18
19
$8,500
20
21
22
23
24
25
26
$9,000
27
28
29
30
31
 $9,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$9,000
3
4
5
6
7
8
9
$12,000
10
11
12
13
14
15
16
$12,000
17
18
19
20
21
22
23
$10,000
24
25
26
27
28
29
30
$10,000
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$6,000
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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HOD28

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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:
$10 - $8,750
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,500
8
9
10
11
12
13
14
$6,500
15
16
17
18
19
20
21
$6,500
22
23
24
25
26
27
28
$7,000
29
30
 $8,750
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,750
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$8,000
20
21
22
23
24
25
26
$8,000
27
28
29
30
31
 $8,750
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,750
3
4
5
6
7
8
9
$8,750
10
11
12
13
14
15
16
$10,350
17
18
19
20
21
22
23
$10,350
24
25
26
27
28
29
30
$8,750
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
 $5,000
Clean Fee: 
$575 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. 

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WESTW

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Property Details
Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis

Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
5
Baths: 
2
Price Range:
$10 - $8,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,500
8
9
10
11
12
13
14
$6,500
15
16
17
18
19
20
21
$6,500
22
23
24
25
26
27
28
$7,500
29
30
 $8,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,500
6
7
8
9
10
11
12
$9,000
13
14
15
16
17
18
19
$9,000
20
21
22
23
24
25
26
$10,000
27
28
29
30
31
 $10,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$10,000
3
4
5
6
7
8
9
$12,000
10
11
12
13
14
15
16
$12,000
17
18
19
20
21
22
23
$12,000
24
25
26
27
28
29
30
$8,500
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$5,500
21
22
23
24
25
26
27
$5,000
28
29
30
 $5,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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VANA2

(0)Inquire/Share
Property Details
Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

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

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Property Details
Beautiful Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$10 - $8,300
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
$7,500
29
30
 $7,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,800
6
7
8
9
10
11
12
$7,800
13
14
15
16
17
18
19
$7,800
20
21
22
23
24
25
26
$7,800
27
28
29
30
31
 $8,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,000
3
4
5
6
7
8
9
$8,300
10
11
12
13
14
15
16
$8,300
17
18
19
20
21
22
23
$8,300
24
25
26
27
28
29
30
$7,500
31
 
September 2025
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

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