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Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC

This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more

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

Ferry Tickets Available for weeks 6/28-7/5, 7/19-7/26 & 7/26-8/2 - please inquire

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BELAT

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Property Details
West Tisbury Country Setting, Access to Association Pool and Tennis, A/C, Wifi

Spacious, light-filled home set in a lovely community with AC and a well-equipped kitchen. The sun room opens to the deck which overlooks a lovely, private yard.  A combined living and dining...Read more

Location: 
West Tisbury
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,300 - $3,300
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
29
30
 $3,300
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,300
6
7
8
9
10
11
12
$3,300
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 $3,400
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,400
3
4
5
6
7
8
9
$3,400
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 $2,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,600
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: 
$250 per week
Tax: State & Local: 
11.7
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BELLJ

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Property Details
Gorgeous Beach Retreat, 20 x 40 Heated Pebble Tec Pool, Tennis Courts, Walk or Bike to South Beach

Ferry Tickets available 7/13-7/20  & 7/20 to 7/27.  Inquire for details! (mv)

This stunning newly updated contemporary beach home is just steps from South Beach, and even fewer steps to the bike...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
4
Baths: 
3
Price Range:
$10,000 - $30,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$15,000
8
9
10
11
12
13
14
$15,000
15
16
17
18
19
20
21
$20,000
22
23
24
25
26
27
28
$20,000
29
30
 $25,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$25,000
6
7
8
9
10
11
12
$25,000
13
14
15
16
17
18
19
$25,000
20
21
22
23
24
25
26
$25,000
27
28
29
30
31
 $30,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$30,000
3
4
5
6
7
8
9
$30,000
10
11
12
13
14
15
16
$30,000
17
18
19
20
21
22
23
$30,020
24
25
26
27
28
29
30
$25,000
31
 $20,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$20,000
7
8
9
10
11
12
13
$15,000
14
15
16
17
18
19
20
$15,000
21
22
23
24
25
26
27
$15,000
28
29
30
 $11,000
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Ferry Tickets available 7/13-7/20  & 7/20 to 7/27.  Inquire for details! (mv)

 

Pool Heated to 82 included in rental rate July & August weeks.

Pool heated to 82 additional $300 per week June & September, May & October pool heated to 82 additional $400 per week

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BERNC

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Property Details
Mini Retreat with Pool, Private Peaceful Chilmark Location, Lucy Vincent and Menemsha Beaches Nearby.

Impeccably maintained and updated, this adorable summer home is perfect for families looking for luxury features such as quality linens in a quiet location. The 12 by 18-foot spa pool is...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,710 - $13,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,350
8
9
10
11
12
13
14
$7,350
15
16
17
18
19
20
21
$8,000
22
23
24
25
26
27
28
$12,400
29
30
 $13,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$13,000
6
7
8
9
10
11
12
$13,000
13
14
15
16
17
18
19
$13,000
20
21
22
23
24
25
26
$13,000
27
28
29
30
31
 $13,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$13,500
3
4
5
6
7
8
9
$13,500
10
11
12
13
14
15
16
$13,500
17
18
19
20
21
22
23
$13,500
24
25
26
27
28
29
30
$13,000
31
 $8,300
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$8,300
7
8
9
10
11
12
13
$7,650
14
15
16
17
18
19
20
$7,650
21
22
23
24
25
26
27
$7,650
28
29
30
 $4,800
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Pool heated to 82 degrees included in rental rate July & August

Pool heated to 82 degrees, May, June Sept and October additional $150 per week propane surcharge

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BERNS

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Property Details
Country Charm, Screened Porch, Large Yard, Bike Paths

Large families enjoy this wonderful summer home.  Conveniently located close to West Tisbury town center.  Great summer spaces for relaxing and enjoying barbeques, lawn games, lunch on the screened porch,...Read more

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

Ferry Tickets Available for weeks  8/17 - 8/24 - please inquire

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BETTD

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Property Details
Outstanding Luxury Family Retreat, Heated Pool, 10 Minute Walk/5 minute Bike Ride to Village Center,

This outstanding custom-built summer vacation home features an 18 X 40 ft heated pool with a bluestone patio surround.  Set on a large private yard, this designer home is just a 10-minute...Read more

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

Ferry Tickets Available for weeks 6/20-6/27 & 7/18-7/25 - please inquire

 

Pool Heated to 81 July & August included in rental rate. Off season pool heat may be extra fee, please inquire! 

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BETTE

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Property Details
Luxury Gambrel Home. Heated Pool, Bluestone Patio Surround, Patio Dining, Walk to Town, 4 Bedrooms, 3.5 Baths

Unwind with family and friends in this newly constructed vacation home, featuring a heated pool and ideally situated on a peaceful lane, just a short stroll to the village center....Read more

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

Ferry Tickets Available for weeks 6/21-6/28, 7/5-7/12, 7/12-7/19, 8/30-9/6 - please inquire

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BIALS

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Property Details
Chilmark, Charming Updated Menemsha Home. Water Views & Sunset Views, Quintessential Beach House.

On a hilltop overlooking the ocean in Menemsha sits this authentic Vineyard home. From one of the most desirable locations on the island, it's an easy walk to the...Read more

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

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Property Details
East Chop Area, Tri-Level Home with Distant Water views, Located just 1.5 Mi to Oak Bluffs Center

Beautiful summer home with distant water views, located in the desirable East Chop neighborhood.  This 4 bedroom, 3 bath home is located just 1.5 miles from Oak Bluffs Center & Beach. 

The...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$5,550 - $7,150
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,550
8
9
10
11
12
13
14
$6,000
15
16
17
18
19
20
21
$6,500
22
23
24
25
26
27
28
$6,500
29
30
 $7,150
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,150
6
7
8
9
10
11
12
$7,150
13
14
15
16
17
18
19
$7,150
20
21
22
23
24
25
26
$7,150
27
28
29
30
31
 $7,150
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,150
3
4
5
6
7
8
9
$7,150
10
11
12
13
14
15
16
$7,150
17
18
19
20
21
22
23
$7,150
24
25
26
27
28
29
30
$7,150
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
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
 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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BLACJ

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Property Details
Long Point Beach House, All New Primary Suite, Expansive Sun Porch with Living and Dining Areas, Expansive Deck, Private Yard

This Beach-chic Long Point retreat has just undergone an update in most areas with an all-new Primary Bedroom suite and expansive sun porch hosting both living and dining areas and decorated in nautical...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$2,700 - $7,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,700
8
9
10
11
12
13
14
$2,700
15
16
17
18
19
20
21
$2,700
22
23
24
25
26
27
28
$4,850
29
30
 $7,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
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
 $7,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,500
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
$7,500
24
25
26
27
28
29
30
$7,500
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
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

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