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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 - $18,000
June 2026
SuMoTuWeThFrSaWeek
 1
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3
4
5
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$8,500
7
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$8,500
14
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$11,000
21
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$14,000
28
29
30
 $18,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$18,000
5
6
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$18,000
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$18,000
19
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$18,000
26
27
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30
31
 $20,000
August 2026
SuMoTuWeThFrSaWeek
 1
$20,000
2
3
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5
6
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8
$20,000
9
10
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$21,000
16
17
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21
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$21,500
23
24
25
26
27
28
29
$18,000
30
31
 $10,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
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$10,000
13
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$10,000
20
21
22
23
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25
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$9,000
27
28
29
30
 $9,000
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 2026
SuMoTuWeThFrSaWeek
 1
2
3
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11
12
13
14
15
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22
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25
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27
28
29
30
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,700
5
6
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10
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$4,700
12
13
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$4,700
19
20
21
22
23
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25
$4,700
26
27
28
29
30
31
 $4,900
August 2026
SuMoTuWeThFrSaWeek
 1
$4,900
2
3
4
5
6
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September 2026
SuMoTuWeThFrSa
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27
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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 - $10,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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7
8
9
10
11
12
13
14
15
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18
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20
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22
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25
26
27
$8,300
28
29
30
 $10,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,000
5
6
7
8
9
10
11
$10,000
12
13
14
15
16
17
18
$10,500
19
20
21
22
23
24
25
$10,500
26
27
28
29
30
31
 $11,000
August 2026
SuMoTuWeThFrSaWeek
 1
$11,000
2
3
4
5
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$11,000
9
10
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$11,000
16
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$11,000
23
24
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28
29
$9,000
30
31
 $9,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,000
6
7
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9
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12
$5,500
13
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$5,500
20
21
22
23
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25
26
$5,500
27
28
29
30
 $5,500
Clean Fee: 
$600 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 - $2,700
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,250
7
8
9
10
11
12
13
$2,300
14
15
16
17
18
19
20
$2,700
21
22
23
24
25
26
27
$2,900
28
29
30
 $3,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,200
5
6
7
8
9
10
11
$3,200
12
13
14
15
16
17
18
$3,200
19
20
21
22
23
24
25
$3,200
26
27
28
29
30
31
 $3,300
August 2026
SuMoTuWeThFrSaWeek
 1
$3,300
2
3
4
5
6
7
8
$3,300
9
10
11
12
13
14
15
$3,300
16
17
18
19
20
21
22
$3,300
23
24
25
26
27
28
29
$2,900
30
31
 $2,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,000
6
7
8
9
10
11
12
$2,000
13
14
15
16
17
18
19
$2,000
20
21
22
23
24
25
26
$2,000
27
28
29
30
 $1,900
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:
$13,000 - $15,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
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15
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$15,000
28
29
30
 $13,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$13,000
5
6
7
8
9
10
11
$13,000
12
13
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15
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17
18
$13,000
19
20
21
22
23
24
25
$13,000
26
27
28
29
30
31
 $13,000
August 2026
SuMoTuWeThFrSaWeek
 1
$13,000
2
3
4
5
6
7
8
$15,000
9
10
11
12
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14
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$15,000
16
17
18
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20
21
22
$15,000
23
24
25
26
27
28
29
30
31
 
September 2026
SuMoTuWeThFrSa
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2
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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 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSa
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August 2026
SuMoTuWeThFrSa
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September 2026
SuMoTuWeThFrSa
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28
29
30
 
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 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,200
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
$4,000
28
29
30
 $5,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$5,500
12
13
14
15
16
17
18
$5,500
19
20
21
22
23
24
25
$5,600
26
27
28
29
30
31
 $5,800
August 2026
SuMoTuWeThFrSaWeek
 1
$5,800
2
3
4
5
6
7
8
$5,800
9
10
11
12
13
14
15
$5,800
16
17
18
19
20
21
22
$5,800
23
24
25
26
27
28
29
$5,400
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$3,200
13
14
15
16
17
18
19
$3,200
20
21
22
23
24
25
26
$3,200
27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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GRAND

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Property Details
Lovely Edgartown Home, Private Location just 1.5 Miles to Village Center, Pool, 5 Bedrooms, 4.5 Baths, Sleeps 10

Charming 5-Bedroom, 4.5-Bath Home with Pool: Nestled in a private setting, this cozy home features a large above-ground pool, perfect for relaxation and fun, a private yard, and a large deck...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$0 - $0
June 2026
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
 $10,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,000
5
6
7
8
9
10
11
$9,000
12
13
14
15
16
17
18
$9,000
19
20
21
22
23
24
25
$9,000
26
27
28
29
30
31
 $10,000
August 2026
SuMoTuWeThFrSaWeek
 1
$10,000
2
3
4
5
6
7
8
$12,000
9
10
11
12
13
14
15
$12,000
16
17
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19
20
21
22
$12,000
23
24
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29
$12,000
30
31
 
September 2026
SuMoTuWeThFrSa
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2
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25
26
27
28
29
30
 
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7
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GRATD

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Property Details
Located in the Heart of Oak Bluffs, 5 Minute Walk to OB Center and 2 Blocks to the Beach
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
2
Price Range:
$2,000 - $4,700
June 2026
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
$4,000
21
22
23
24
25
26
27
$4,300
28
29
30
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,700
5
6
7
8
9
10
11
$4,700
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,700
26
27
28
29
30
31
 $4,700
August 2026
SuMoTuWeThFrSaWeek
 1
$4,700
2
3
4
5
6
7
8
$4,700
9
10
11
12
13
14
15
$4,700
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 $4,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$4,100
13
14
15
16
17
18
19
$3,900
20
21
22
23
24
25
26
$3,300
27
28
29
30
 $2,700
Clean Fee: 
$260 per week
Tax: State & Local: 
11.7
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GRILJ

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Property Details
Lovely Custom Post & Beam Home, Tucked on Gorgeous Private Acreage, 1.5 Miles from the Center of Vineyard Haven.

Complete Detailed Description to follow soon. 

Attention Parents: Please be aware that the stairs leading to the 2nd-level primary bedroom do not meet current building codes but are grandfathered in....Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,700 - $6,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
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
$3,500
28
29
30
 $4,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,800
5
6
7
8
9
10
11
$4,800
12
13
14
15
16
17
18
$4,800
19
20
21
22
23
24
25
$4,800
26
27
28
29
30
31
 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$5,500
2
3
4
5
6
7
8
$6,000
9
10
11
12
13
14
15
$6,000
16
17
18
19
20
21
22
$6,000
23
24
25
26
27
28
29
$5,200
30
31
 $3,500
September 2026
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
 $3,000
Clean Fee: 
$575
Tax: State & Local: 
11.7

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