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Waterfront & Beachfront

The Beach House  There are few homes anywhere on the island directly on a sandy swimming beach like Beach House. If you love a sunset, and water views that seemingly never...Read more

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

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Property Details
Spacious Home with Heated Pool, Pool Bar with TV, Patio Surround, Deck Overlooking the Pool & Yard, Centrally Located

Spacious home with private heated pool & hot tub, tucked away in a quiet neighborhood, centrally located providing easy access to beaches and towns.  The pool, patio area, deck, & pool bar...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $6,820
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,820
8
9
10
11
12
13
14
$6,820
15
16
17
18
19
20
21
$6,820
22
23
24
25
26
27
28
$6,820
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
 $6,820
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,820
7
8
9
10
11
12
13
$6,820
14
15
16
17
18
19
20
$6,820
21
22
23
24
25
26
27
$6,820
28
29
30
 $6,820
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees included in the rental rate, July & August

Pool Heated to 80 degrees, June & September, additional 350 per week surcharge

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HALLL

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Property Details
Makonikey, Water View, Walk to Private Association Beach, Large Yard Area.

Located in Makonikey,  a private enclave of homes on the North Shore.

Beautifully maintained four-bedroom vacation home with water views. Just a short walk or drive to private Makonikey association beach,  This...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$10 - $4,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,800
8
9
10
11
12
13
14
$3,800
15
16
17
18
19
20
21
$3,800
22
23
24
25
26
27
28
$4,400
29
30
 $4,500
July 2025
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
31
 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,500
3
4
5
6
7
8
9
$4,500
10
11
12
13
14
15
16
$4,500
17
18
19
20
21
22
23
$4,500
24
25
26
27
28
29
30
$4,500
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$3,800
14
15
16
17
18
19
20
$3,800
21
22
23
24
25
26
27
$3,800
28
29
30
 $3,500
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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HANRJ

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Property Details
Spacious Oak Bluffs Contemporary Home, 4 Bedrooms & 4 Baths, Quiet Private Location in Bayes Hill Community of Homes

Privately situated on the outskirts of Oak Bluffs, yet centrally located to towns and beaches. The home features a large patio area with outdoor dining and grill area and a spacious...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$10 - $7,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,300
8
9
10
11
12
13
14
$4,300
15
16
17
18
19
20
21
$4,300
22
23
24
25
26
27
28
$4,500
29
30
 $5,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$5,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
31
 $5,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,500
3
4
5
6
7
8
9
$7,000
10
11
12
13
14
15
16
$7,000
17
18
19
20
21
22
23
$7,000
24
25
26
27
28
29
30
$5,500
31
 $5,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
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
 $3,500
Clean Fee: 
$575
Tax: State & Local: 
11.7

 

 

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HARTM

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Property Details
Charming & Cozy 2 Bedroom, 2 Bath Home, West Chop area of Vineyard Haven, Located on a Quiet Street, Close to Town & Beach

Ideally located in the West Chop woods area of Vineyard Haven, just 1 mile to town center and the business district, and a 10 to 15-minute drive to various public...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$10 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,850
8
9
10
11
12
13
14
$3,850
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $4,650
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,650
6
7
8
9
10
11
12
$4,850
13
14
15
16
17
18
19
$4,850
20
21
22
23
24
25
26
$4,850
27
28
29
30
31
 $4,850
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,850
3
4
5
6
7
8
9
$5,150
10
11
12
13
14
15
16
$5,150
17
18
19
20
21
22
23
$5,150
24
25
26
27
28
29
30
$5,150
31
 $3,300
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,300
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
 $2,700
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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HERGT

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Property Details
Luxury Retreat Chilmark, Key to Quansoo Private Association Beach, Heated Pool, Stone Patio, Pool Pavillion, Propane Fire Pit, Set on 7.5 private acres

New for 2024: Heated Pool with Patio Surround, Propane Fire Pit,  Post and Beam Pool Pavillion with outdoor kitchen hosting 36" Lynx Grill,  Lynx Sink, Power Burner, undercounter Fridge and dishwasher, Raised...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10 - $18,500
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
$18,500
29
30
 $20,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$20,500
6
7
8
9
10
11
12
$20,500
13
14
15
16
17
18
19
$22,500
20
21
22
23
24
25
26
$22,500
27
28
29
30
31
 $25,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$25,000
3
4
5
6
7
8
9
$25,000
10
11
12
13
14
15
16
$25,000
17
18
19
20
21
22
23
$25,000
24
25
26
27
28
29
30
$18,500
31
 $18,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$18,500
7
8
9
10
11
12
13
$18,500
14
15
16
17
18
19
20
$18,500
21
22
23
24
25
26
27
$18,500
28
29
30
 
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

Pool will be heated to 82 degrees July and August included in rental rate.

 

Pool Heated to 82 degrees June & Sept weeks $300/week 

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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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HODGE

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Property Details
Stunning Waterfront Home on the Lagoon, Complete Renovation and Professionally Decorated. Private Beach Area and Dock, Perfect Retreat for Extended Families, Walk to Town. Swim, Sun, Kayak or Bring your own boat.

Exquisite waterfront family compound sleeps 12, with 270-degree water view of the Lagoon,  85' of sandy beach on the lagoon, and a private dock for boaters. Private dock (12' draft) with mooring and private sandy...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
6
Baths: 
4
Price Range:
$10 - $25,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,000
8
9
10
11
12
13
14
$17,500
15
16
17
18
19
20
21
$17,500
22
23
24
25
26
27
28
$17,500
29
30
 $30,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$30,000
6
7
8
9
10
11
12
$30,000
13
14
15
16
17
18
19
$30,000
20
21
22
23
24
25
26
$30,000
27
28
29
30
31
 $25,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$25,000
3
4
5
6
7
8
9
$35,000
10
11
12
13
14
15
16
$35,000
17
18
19
20
21
22
23
$35,000
24
25
26
27
28
29
30
$25,000
31
 $17,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$17,500
7
8
9
10
11
12
13
$15,000
14
15
16
17
18
19
20
$14,000
21
22
23
24
25
26
27
$14,000
28
29
30
 $15,500
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Private Dock plus Mooring that draws 12 feet. If you plan to bring a boat please speak with the agent for details as must be approved by owner!

 

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HODGW

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Property Details
New Tri Level Luxury Home, Heated Pool with Bluestone Patio Surround

Location location!

Just 1 mile from Oak Bluffs center this stunning 5 bedroom, 4.5 bath features a gunite pool with a bluestone patio surround, sure to be the focal point...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$10 - $17,300
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
$13,300
22
23
24
25
26
27
28
$15,000
29
30
 $15,400
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$15,400
6
7
8
9
10
11
12
$15,400
13
14
15
16
17
18
19
$15,400
20
21
22
23
24
25
26
$16,500
27
28
29
30
31
 $16,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$16,500
3
4
5
6
7
8
9
$17,300
10
11
12
13
14
15
16
$17,300
17
18
19
20
21
22
23
$17,300
24
25
26
27
28
29
30
$17,300
31
 $17,050
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$17,050
7
8
9
10
11
12
13
$15,400
14
15
16
17
18
19
20
$15,400
21
22
23
24
25
26
27
$15,400
28
29
30
 $12,500
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

Ferry Tickets available for weeks 6.21-6.28, 6.28-7.5, 8.23-8.30 - please inquire

 

Pool Heated to 81 included in rental rate, July and August weeks

 

June & September weeks to 81 degrees additional $500 fee. Higher temp upon request additional fee

 

Notice: Ring doorbell cameras are located on the front entry door and door on the left/parking side of the house:

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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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