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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 - $24,000
June 2027
SuMoTuWeThFrSaWeek
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$15,000
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$15,000
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$15,000
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$15,500
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29
30
 $20,000
July 2027
SuMoTuWeThFrSaWeek
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$20,000
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$20,000
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$20,000
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$20,000
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$24,000
August 2027
SuMoTuWeThFrSaWeek
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$27,500
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$27,500
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$24,000
22
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$22,500
29
30
31
 $18,500
September 2027
SuMoTuWeThFrSaWeek
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$18,500
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$18,500
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$18,500
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$18,500
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27
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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, For 2027 this Home is Under the code MUCCJ

Experience refined coastal living at this exceptional cottage- style waterfront retreat in the coveted East Chop area of Oak Bluffs. 

This idyllic waterfront summer sanctuary is poised to create cherished...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$8,000 - $8,000
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Owner reduced rate for weeks 8/15 & 8/22 - see calendar for adjusted rates

This property is under a new code for the 2027 season.  Please see MUCCJ

 

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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:
$3,900 - $4,900
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$450 per week, $600 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. The property backs up...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10,000 - $16,500
June 2027
SuMoTuWeThFrSaWeek
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$11,000
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$11,000
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$13,500
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$16,000
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 $16,500
July 2027
SuMoTuWeThFrSaWeek
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$16,500
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$16,500
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$15,500
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$16,000
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$17,000
August 2027
SuMoTuWeThFrSaWeek
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$18,500
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$18,500
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$18,500
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$16,500
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30
31
 $12,500
September 2027
SuMoTuWeThFrSaWeek
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$12,500
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$10,000
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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:
$5,000 - $9,750
June 2027
SuMoTuWeThFrSaWeek
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$5,000
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$5,750
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$5,750
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$7,500
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 $9,750
July 2027
SuMoTuWeThFrSaWeek
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$9,750
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$9,750
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$9,750
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$9,750
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$9,750
August 2027
SuMoTuWeThFrSaWeek
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$9,750
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$9,750
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$9,750
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$9,750
29
30
31
 $7,500
September 2027
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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$5,750
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$5,750
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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:
$2,800 - $4,160
June 2027
SuMoTuWeThFrSaWeek
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2
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5
$3,100
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$3,100
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$3,100
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$3,100
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28
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 $3,850
July 2027
SuMoTuWeThFrSaWeek
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$3,850
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$3,850
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$3,850
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$3,850
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$3,850
August 2027
SuMoTuWeThFrSaWeek
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$4,160
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$4,160
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$4,160
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$4,160
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 $4,160
September 2027
SuMoTuWeThFrSaWeek
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$4,160
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$3,800
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$3,800
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$3,800
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30
 $3,800
Clean Fee: 
$250 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 2027
SuMoTuWeThFrSaWeek
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2
3
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5
$5,800
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$5,800
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$6,800
27
28
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30
 $11,000
July 2027
SuMoTuWeThFrSaWeek
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$11,000
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$11,000
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$11,000
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$12,000
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$12,000
August 2027
SuMoTuWeThFrSaWeek
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$12,000
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$12,000
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$12,000
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$10,000
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 $7,000
September 2027
SuMoTuWeThFrSaWeek
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$7,000
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$6,500
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$6,500
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$6,500
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 $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:
$4,500 - $4,500
June 2027
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July 2027
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August 2027
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

 Ferry Tickets available weeks 8/30 to 9/5 and 9/5 to 9/12 - please inquire

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Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$2,500 - $6,000
June 2027
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$4,000
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 $5,000
July 2027
SuMoTuWeThFrSaWeek
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$5,000
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$5,000
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$5,000
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$5,000
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$5,000
August 2027
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
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$8,000
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$6,000
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 $6,000
September 2027
SuMoTuWeThFrSaWeek
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$6,000
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$3,000
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$3,000
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$3,000
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30
 $3,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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Tashmoo Cove Townhouse, Association Pool, Association Tennis Courts.

MVVR Exclusive: Beautifully appointed with a mix of Asian and Tibetan antique furniture, furnishings from Napa Valley, Sundance, and Pottery Barn, and original artwork, this highly desirable townhouse provides a luxurious...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$2,200 - $4,900
June 2027
SuMoTuWeThFrSaWeek
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5
$3,270
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$3,270
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$3,270
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$3,270
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28
29
30
 $4,400
July 2027
SuMoTuWeThFrSaWeek
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2
3
$4,400
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$4,400
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$4,400
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$4,400
25
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30
31
$4,800
August 2027
SuMoTuWeThFrSaWeek
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7
$4,900
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$4,900
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$4,900
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27
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$4,450
29
30
31
 $3,150
September 2027
SuMoTuWeThFrSaWeek
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4
$3,150
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$3,150
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$2,750
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$2,250
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29
30
 $2,250
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

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