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Stunning Historic Home, Nicely Renovated with Luxury Details throughout, AC, View of Harbor from 2nd Level Porch

Quintessential, historic in-town Vineyard home, just steps from the beach and ferry.  Water views of Vineyard Haven Harbor. This totally renovated house is designed to create the perfect Vineyard vacation. ...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2025
SuMoTuWeThFrSaWeek
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 $6,000
July 2025
SuMoTuWeThFrSaWeek
 1
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$6,000
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$6,000
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$6,000
20
21
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$6,700
27
28
29
30
31
 $7,300
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,300
3
4
5
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$7,300
10
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$7,300
17
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$7,300
24
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$7,000
31
 $5,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,700
7
8
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$5,700
14
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$5,700
21
22
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24
25
26
27
$5,700
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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GEORS

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Property Details
Family Friendly Edgartown Home, Heated Pool, 12' x 25', Screened Porch, Deck, Ideally Located, 5 Minute Drive to South Beach and Edgartown Village

This lovely spacious home is tucked away in Island Grove just on the outskirts of Edgartown Village.  The outdoor living spaces include a heated pool with patio area, screened porch with...Read more

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

Pool heated to 80 degrees, June through September included in rental rate!

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GIAMJ

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Property Details
Meetinghouse Middle Condo, Association Pool, Central Air

Set in quiet Meeting House Village on the outskirts of Edgartown, this lovely condominium unit features a spacious open main living level with glass sliders leading out to the deck with a...Read more

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

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Property Details
Stunning New Custom Luxury Home, Oak Bluffs, 18 x 36 Heated Saltwater Pool, Bluestone Patio, 4 Bedrooms 3.5 baths

Tucked just on the outskirts of Oak Bluffs downtown area this spacious architect-designed custom home offers families and friends an outstanding vacation experience. 

Professionally designed by a noted architect this outstanding...Read more

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

Pool Heated to 81 degrees July & August included in Rental Rate

Pool Heated to 81 degrees June & September additional $300 Propane Surcharge

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GLOVL

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Property Details
Lovely Contemporary Home, Quiet Location in Pond View, Private Back Yard, Porch & Deck

Beautifully maintained, family-friendly home.

Lovely 3 Bedroom, 2.5 bath home situated in a quiet enclave of homes known as Pond View and just 2.5 miles to the center of Oak Bluffs....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,700 - $4,900
June 2025
SuMoTuWeThFrSaWeek
1
2
3
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 $4,700
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
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$4,700
13
14
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18
19
$4,700
20
21
22
23
24
25
26
$4,700
27
28
29
30
31
 $4,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,900
3
4
5
6
7
8
9
$4,900
10
11
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15
16
$4,900
17
18
19
20
21
22
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$4,900
24
25
26
27
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29
30
$4,900
31
 
September 2025
SuMoTuWeThFrSa
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2
3
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5
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10
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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: 
$350 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:
$5,500 - $11,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
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30
 $10,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
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10
11
12
$10,000
13
14
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18
19
$10,000
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
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10
11
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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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GOLLB

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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:
$1,850 - $3,250
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
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10
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13
14
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26
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28
29
30
 $3,150
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,150
6
7
8
9
10
11
12
$3,150
13
14
15
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18
19
$3,150
20
21
22
23
24
25
26
$3,150
27
28
29
30
31
 $3,250
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,250
3
4
5
6
7
8
9
$3,250
10
11
12
13
14
15
16
$3,250
17
18
19
20
21
22
23
$3,250
24
25
26
27
28
29
30
$2,850
31
 $1,950
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$1,950
7
8
9
10
11
12
13
$1,950
14
15
16
17
18
19
20
$1,950
21
22
23
24
25
26
27
$1,950
28
29
30
 $1,850
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

Cottage books Tuesday to Tuesday July & August weeks

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GORDM

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Property Details
Spacious Contemporary Home, New Heated 20 x40 Pool, Beautifully Landscaped. Desirable Deep Bottom Community of Homes, Association Tennis Courts, Shared Dock on Great Pond for Launching Kayaks

Tucked in the exquisite community of homes known as Deep Bottom, this spacious home is sited on 2.78 acres with gorgeous views across horse pasture, pond, and meadows. Adding to the serenity of...Read more

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

Spa on the property is not available for renter use. 

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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:
$0 - $0
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
 $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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GRADL

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Property Details
Charming, Modern, Updated 4 Bedroom Home, 2 Bath, AC, Spacious Private Deck Area

Wonderful newly updated 4 bedroom home, tucked on a culdesac in a quiet but central location to beaches and town centers. The spacious private deck provides additional living space and hosts...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$3,200 - $5,800
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
 $5,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
9
10
11
12
$5,500
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,600
27
28
29
30
31
 $5,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,800
3
4
5
6
7
8
9
$5,800
10
11
12
13
14
15
16
$5,800
17
18
19
20
21
22
23
$5,800
24
25
26
27
28
29
30
$5,400
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$3,200
14
15
16
17
18
19
20
$3,200
21
22
23
24
25
26
27
$3,200
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

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