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Waterfront, Water View, Lagoon Beach

This charming, recently renovated, waterfront home atop the lagoon bluffs, boasts spectacular sunsets and panoramic waterfront views of the Lagoon, outer Vineyard Haven Harbor, and Cape Cod from patios, living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,000 - $4,200
June 2026
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July 2026
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August 2026
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September 2026
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Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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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 - $6,000
June 2026
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
 $5,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
7
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9
10
11
$5,000
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
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
$5,500
16
17
18
19
20
21
22
$6,000
23
24
25
26
27
28
29
$6,000
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
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12
$4,000
13
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18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $3,000
Clean Fee: 
$380 per week
Tax: State & Local: 
11.7
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Deluxe Family & Friends Compound, Heated Pool, 7 bedrooms 5.5 Baths

This exceptional estate is nestled in the prestigious Oyster Pond enclave, located on the outskirts of Edgartown. Set on expansive private grounds, this vacation retreat features 7 bedrooms and 5.5...Read more

Location: 
Edgartown
Sleeps: 
14
Bedrooms: 
7
Baths: 
5
Price Range:
$14,000 - $27,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
6
$15,000
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
$15,500
28
29
30
 $20,000
July 2026
SuMoTuWeThFrSaWeek
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2
3
4
$20,000
5
6
7
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10
11
$20,000
12
13
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18
$20,000
19
20
21
22
23
24
25
$20,000
26
27
28
29
30
31
 $24,000
August 2026
SuMoTuWeThFrSaWeek
 1
$24,000
2
3
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5
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7
8
$27,500
9
10
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12
13
14
15
$27,500
16
17
18
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21
22
$24,000
23
24
25
26
27
28
29
$22,500
30
31
 $18,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
$18,500
6
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12
$18,500
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19
$18,500
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21
22
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25
26
$18,500
27
28
29
30
 $18,500
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

Pool is heated to 81 degrees and included in the rent July & August weeks. Off season May to October there is an additional fee for pool heat. Inquire with an agent for details

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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:
$6,000 - $10,000
June 2026
SuMoTuWeThFrSaWeek
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5
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$6,000
7
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13
$6,000
14
15
16
17
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19
20
$6,000
21
22
23
24
25
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27
$6,000
28
29
30
 $10,000
July 2026
SuMoTuWeThFrSaWeek
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2
3
4
$10,000
5
6
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11
$10,000
12
13
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18
$10,000
19
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22
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25
$10,000
26
27
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29
30
31
 $10,000
August 2026
SuMoTuWeThFrSaWeek
 1
$10,000
2
3
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$10,000
9
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15
$10,000
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22
$10,000
23
24
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28
29
$10,000
30
31
 $8,000
September 2026
SuMoTuWeThFrSaWeek
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$8,000
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$6,000
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$6,000
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$6,000
27
28
29
30
 $6,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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1.5 Acres of Privacy, Bike Paths Adjacent to House, Association Pool, WiFi, Central A/C

West Tisbury - Newly updated and featuring 5 bedrooms and 4 baths.  Recently renovated including all new kitchen, updated baths, flooring, carpeting, walls painted, and lovely furnishings.  There is central AC on the 1st...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$3,500 - $6,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
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13
$4,000
14
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20
$4,000
21
22
23
24
25
26
27
$5,000
28
29
30
 $5,900
July 2026
SuMoTuWeThFrSaWeek
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2
3
4
$5,900
5
6
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$6,250
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$6,250
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25
$6,500
26
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30
31
 $6,500
August 2026
SuMoTuWeThFrSaWeek
 1
$6,500
2
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$6,500
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$6,500
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$6,500
23
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29
$6,500
30
31
 $5,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
$5,900
6
7
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12
$4,900
13
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$4,900
20
21
22
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24
25
26
$4,900
27
28
29
30
 $3,900
Clean Fee: 
$450 per week, $500 per week with pet
Tax: State & Local: 
11.7
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Chic Contemporary Luxury Home, Heated Pool 14 x 31, Private Patio, Screened Porch, Sun Deck, Situated on Large Acreage off of Lambert's Cove Rd. Lambert’s Cove Beach 1 mile.

Lambert’s Cove Area: Beautiful new modern architectural farmhouse, features open living spaces with soaring cathedral ceilings and walls of glass opening out to the patio and yard areas.  Privacy and peace...Read more

Location: 
West Tisbury
Sleeps: 
7
Bedrooms: 
4
Baths: 
3
Price Range:
$10,000 - $17,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$11,000
7
8
9
10
11
12
13
$11,000
14
15
16
17
18
19
20
$13,500
21
22
23
24
25
26
27
$16,000
28
29
30
 $16,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$16,500
5
6
7
8
9
10
11
$16,500
12
13
14
15
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17
18
$15,500
19
20
21
22
23
24
25
$16,000
26
27
28
29
30
31
 $17,000
August 2026
SuMoTuWeThFrSaWeek
 1
$17,000
2
3
4
5
6
7
8
$18,500
9
10
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12
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14
15
$18,500
16
17
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19
20
21
22
$18,500
23
24
25
26
27
28
29
$15,000
30
31
 $12,000
September 2026
SuMoTuWeThFrSaWeek
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2
3
4
5
$12,000
6
7
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10
11
12
13
14
15
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21
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25
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28
29
30
 
Clean Fee: 
$650 per week, $450 interim cleaning on multiple week rentals
Tax: State & Local: 
11.7

Pool Heated to 81 degrees July & August, additional $300 per week propane fee. 

Pool Heated to 81 degrees June & September, additional $300 per week propane fee

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Water view Upper Makonikey Home, Distinctive Design by Royal Barry Wills, Two Private Association Beaches, Central A/C

Classic Royal Barry Wills-designed cedar-shingled Vineyard home, beautifully sited on five private landscaped acres in the exclusive enclave of homes known as Makonikey. Lovely distant water views of Vineyard Sound and...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$4,500 - $9,750
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
7
8
9
10
11
12
13
$5,750
14
15
16
17
18
19
20
$5,750
21
22
23
24
25
26
27
$7,500
28
29
30
 $9,750
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,750
5
6
7
8
9
10
11
$9,750
12
13
14
15
16
17
18
$9,750
19
20
21
22
23
24
25
$9,750
26
27
28
29
30
31
 $9,750
August 2026
SuMoTuWeThFrSaWeek
 1
$9,750
2
3
4
5
6
7
8
$9,750
9
10
11
12
13
14
15
$9,750
16
17
18
19
20
21
22
$9,750
23
24
25
26
27
28
29
$9,750
30
31
 $7,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$5,750
20
21
22
23
24
25
26
$5,750
27
28
29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Waterview Farms, Water view

Lovely contemporary home in one of the island's premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $4,160
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,460
7
8
9
10
11
12
13
$3,460
14
15
16
17
18
19
20
$3,460
21
22
23
24
25
26
27
$3,460
28
29
30
 $4,160
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,160
5
6
7
8
9
10
11
$4,160
12
13
14
15
16
17
18
$4,160
19
20
21
22
23
24
25
$4,160
26
27
28
29
30
31
 $4,160
August 2026
SuMoTuWeThFrSaWeek
 1
$4,160
2
3
4
5
6
7
8
$4,160
9
10
11
12
13
14
15
$4,160
16
17
18
19
20
21
22
$4,160
23
24
25
26
27
28
29
$4,160
30
31
 $4,160
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,160
6
7
8
9
10
11
12
$4,160
13
14
15
16
17
18
19
$4,160
20
21
22
23
24
25
26
$4,160
27
28
29
30
 $4,160
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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Newly refurbished Tri Level, Gorgeous Water Views of North Shore in Exclusive Makonikey Area

Stunning Hilltop Post & Beam Vacation Home with a relaxed coastal ambiance and picturesque distant water vistas! Nestled off Lambert’s Cove Rd in Vineyard Haven, this exquisite property resides within...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$5,000 - $12,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,800
7
8
9
10
11
12
13
$5,800
14
15
16
17
18
19
20
$6,800
21
22
23
24
25
26
27
$8,990
28
29
30
 $11,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000
5
6
7
8
9
10
11
$11,000
12
13
14
15
16
17
18
$11,000
19
20
21
22
23
24
25
$12,000
26
27
28
29
30
31
 $12,000
August 2026
SuMoTuWeThFrSaWeek
 1
$12,000
2
3
4
5
6
7
8
$12,000
9
10
11
12
13
14
15
$12,000
16
17
18
19
20
21
22
$12,000
23
24
25
26
27
28
29
$10,000
30
31
 $7,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
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
 $5,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

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Gorgeous Water views, set in private Mink Meadows Golf Course Community , Private Association Beach, Walk or drive to the Golf Course Club House

Beautiful home in Mink Meadows area of West Chop.  Guests will enjoy the gorgeous water views across Mink Meadows Pond to the North Shore. Swans, geese, and ducks reside in the...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $7,900
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$5,200
14
15
16
17
18
19
20
$5,200
21
22
23
24
25
26
27
$5,200
28
29
30
 $7,750
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,750
5
6
7
8
9
10
11
$7,750
12
13
14
15
16
17
18
$7,750
19
20
21
22
23
24
25
$7,750
26
27
28
29
30
31
 $7,900
August 2026
SuMoTuWeThFrSaWeek
 1
$7,900
2
3
4
5
6
7
8
$7,900
9
10
11
12
13
14
15
$7,900
16
17
18
19
20
21
22
$7,900
23
24
25
26
27
28
29
$7,900
30
31
 $4,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

 

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