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Exquisite New Luxurious Home, Tucked in the Private Enclave, Known as -The Preserve, Heated Saltwater Pool 18' x 45, Screened Porch, Propane Fire pit with Adirondack Seating, Designer Interior

"The Preserve" in Oak Bluffs is a desirable enclave of homes that offers a serene and alluring living environment. This expansive luxury home designed by noted architect Chuck Sullivan was completed...Read more

Location: 
Oak Bluffs
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$17,500 - $27,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$20,000
8
9
10
11
12
13
14
$20,000
15
16
17
18
19
20
21
$22,500
22
23
24
25
26
27
28
$25,000
29
30
 $27,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$27,000
6
7
8
9
10
11
12
$27,000
13
14
15
16
17
18
19
$27,000
20
21
22
23
24
25
26
$27,000
27
28
29
30
31
 $28,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$28,500
3
4
5
6
7
8
9
$30,000
10
11
12
13
14
15
16
$32,500
17
18
19
20
21
22
23
$32,500
24
25
26
27
28
29
30
$27,000
31
 $20,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$20,000
7
8
9
10
11
12
13
$17,500
14
15
16
17
18
19
20
$17,500
21
22
23
24
25
26
27
$17,500
28
29
30
 
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

Pool Heated to 82 degrees  July & August  weeks, included in the rental rate

Pool Heated to 82 degrees June & September weeks, additional $300 per week surcharge

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CARDA

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Property Details
Essence of Chilmark Living, Tucked on High Knoll Providing Expansive Waterviews of the Atlantic, Luxurious Custom Design, Lush Gardens, 5 minute Drive to Lucy Vincent Beach

Experience the essence of Martha's Vineyard with family and friends at this exceptional home nestled on Peaked Hill in Chilmark, offering breathtaking views of the Atlantic. Set on 8 acres...Read more

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

Transferrable Ferry Tickets some weeks. Please Inquire for Details  (mv)

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CARLB

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Property Details
Upscale Designer Interior, Features 3 Living Spaces, Pool Table, Ping Pong Table, Large Deck, Central A/C, WiFi, Conveniently Located to Towns and Beaches

Beautifully renovated large cape, centrally located in the desirable community of Dodger's Hole.  This lovely 4 bedroom home features a large custom kitchen with upscale appliances and breakfast bar, an...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,200 - $4,700
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
$4,700
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
$5,000
20
21
22
23
24
25
26
$5,500
27
28
29
30
31
 $5,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,500
3
4
5
6
7
8
9
$5,500
10
11
12
13
14
15
16
$5,500
17
18
19
20
21
22
23
$5,500
24
25
26
27
28
29
30
$4,000
31
 $4,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,700
7
8
9
10
11
12
13
$4,700
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,500
28
29
30
 $4,500
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
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CAROB

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Property Details
Beautifully Updated and Newly Furnished, 4 Bedrooms, 3 Baths, Multiple Living Spaces, Centrally Located to Down Island Towns and Beaches.

This charming newly renovated home boasts an airy, open floor plan on the main level featuring a wall of glass sliders that open onto a spacious deck area complete with a...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $6,250
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,200
8
9
10
11
12
13
14
$3,200
15
16
17
18
19
20
21
$3,200
22
23
24
25
26
27
28
$4,000
29
30
 $6,250
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,250
6
7
8
9
10
11
12
$6,250
13
14
15
16
17
18
19
$6,250
20
21
22
23
24
25
26
$7,000
27
28
29
30
31
 $5,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,900
3
4
5
6
7
8
9
$6,500
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
$6,000
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
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
 $3,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Transferrable Ferry Ticket for Sale, 7/5 to 7/12 (mv). Please inquire for details 

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CARON

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Property Details
Exquisite, Contemporary Home, Katama Area of Edgartown, Newly Remodeled and Newly Furnished, Outdoor Kitchen and Lounge Area Area

Nestled in the heart of the Katama Area of Edgartown, this contemporary home draws inspiration from the coastal surroundings. Just a 5-minute drive to Edgartown Village Center and an 8-minute...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
5
Baths: 
4
Price Range:
$8,000 - $13,000
June 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
 
July 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
31
 
August 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
$15,000
10
11
12
13
14
15
16
$15,000
17
18
19
20
21
22
23
$15,000
24
25
26
27
28
29
30
$13,000
31
 $9,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$9,000
7
8
9
10
11
12
13
$8,000
14
15
16
17
18
19
20
$8,000
21
22
23
24
25
26
27
$8,000
28
29
30
 
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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CAS65

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Property Details
Sophisticated, Contemporary Vacation Retreat, Main & Guest House, Heated Pool, Outdoor Living Area, Pond Access for Paddle Boarding and Kayaking, Private Location

A light-filled, coastal-inspired luxury vacation home and guest house tucked in a private location featuring views of Watcha Pond, multiple living spaces, a gourmet kitchen, 4 bedrooms, 4 luxury bathrooms, and the ability to...Read more

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

Pool heated to 81 degrees included in rental rate July to 8/26.  Pool heated to 81 degrees June & September weeks additional $300 propane surcharge weekly.  

 

Main House only may be rented the weeks of  5/24 to 6/20, and 9/2 to 9/30 for $2000 less than the posted rate for Main and Guest House. Inquire for further details!

 

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CASED

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Property Details
Deep Bottom Pond, Private Heated Pool, Central Air, WiFi, Gorgeous Views

Contemporary home in the Deep Bottom area of West Tisbury. This gracious home with a pool and patio overlooks the open meadowland that is the Deep Bottom. The home is...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$6,800 - $12,900
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,800
8
9
10
11
12
13
14
$6,800
15
16
17
18
19
20
21
$7,500
22
23
24
25
26
27
28
$12,500
29
30
 $12,900
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,900
6
7
8
9
10
11
12
$12,900
13
14
15
16
17
18
19
$12,900
20
21
22
23
24
25
26
$12,900
27
28
29
30
31
 $12,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$12,900
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
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: 
$475 per week
Tax: State & Local: 
11.7

Pool Heated to 82 degrees mid June to mid Sept, pool heat costs included in rental rate.

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CASHK

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Property Details
Lovely Home, Centrally Located, Bike Paths, AC all Rooms

This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window AC in all rooms, and a well-equipped modern kitchen. The home is nicely situated...Read more

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

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Property Details
East Chop Waterfront, Extraordinary Sunsets &Views Across the Sound , Deck directly on the Beach, Casual Interior

Classic, casual beachfront home combines cottage styling with modern amenities. spectacular views, quietly lapping waves right outside your windows, and breathtaking sunsets. Ideally located in the East Chop Area of Oak Bluffs just a short distance...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,000 - $13,800
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,000
8
9
10
11
12
13
14
$5,000
15
16
17
18
19
20
21
$5,000
22
23
24
25
26
27
28
$6,000
29
30
 $9,700
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,700
6
7
8
9
10
11
12
$9,700
13
14
15
16
17
18
19
$9,700
20
21
22
23
24
25
26
$9,700
27
28
29
30
31
 $9,700
August 2025
SuMoTuWeThFrSaWeek
 1
2
$9,700
3
4
5
6
7
8
9
$13,800
10
11
12
13
14
15
16
$13,800
17
18
19
20
21
22
23
$13,800
24
25
26
27
28
29
30
$11,200
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$6,000
28
29
30
 
Clean Fee: 
$480 per week
Tax: State & Local: 
11.7

Rates reduced for available weeks - see calendar for adjusted rates

 

 

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CENCR

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Property Details
Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Great Area for Kayaking.

Spacious sun-filled home features open living spaces, hardwood floors throughout, 4 bedrooms and sleeps 8.

Exterior features include two decks, one sunny deck at the front of the house, and a large private...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $11,800
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $4,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,800
6
7
8
9
10
11
12
$4,800
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$5,200
27
28
29
30
31
 $5,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,800
3
4
5
6
7
8
9
$8,800
10
11
12
13
14
15
16
$11,800
17
18
19
20
21
22
23
$11,800
24
25
26
27
28
29
30
$5,800
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
$3,500
21
22
23
24
25
26
27
$3,000
28
29
30
 $3,000
Clean Fee: 
$480 per week
Tax: State & Local: 
11.7

Rates just reduced on available weeks - see calendar for adjusted rates

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