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Stunning Historic Home, Nicely Renovated with Luxury Details throughout, AC, View of Harbor from 2nd Level Porch

Quintessential, historic in-town Vineyard home, just steps from the beach and ferry.  Water views of Vineyard Haven Harbor. This totally renovated house is designed to create the perfect Vineyard vacation. ...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2026
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 $6,250
July 2026
SuMoTuWeThFrSaWeek
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$6,250
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$6,250
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$6,250
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$6,950
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 $7,550
August 2026
SuMoTuWeThFrSaWeek
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$7,550
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$7,550
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$7,550
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$7,550
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$7,550
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September 2026
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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CLASSIC, IN-TOWN EDGARTOWN, ENGLISH-COUNTRY CHIC LUXURY HOME WITH POOL AND MANICURED GROUNDS

Exquisite home in the village of Edgartown that exudes classic taste with English-Country styling.  This in-town location makes it easy to stroll down to dinner on the harbor or walk...Read more

Location: 
Edgartown
Sleeps: 
12
Bedrooms: 
7
Baths: 
6
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$12,500
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$12,500
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$15,000
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$25,000
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29
30
 $29,500
July 2026
SuMoTuWeThFrSaWeek
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$29,500
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$29,500
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$29,500
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$29,500
26
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30
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 $29,500
August 2026
SuMoTuWeThFrSaWeek
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$29,500
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$29,500
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$29,500
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$29,500
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$29,500
30
31
 $12,500
September 2026
SuMoTuWeThFrSaWeek
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$12,500
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$10,500
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$10,500
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$10,500
27
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29
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 $10,500
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7
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Stylish Contemporary Vacation Home situated in Meadow View Farms, Open Light Filled Design, Expansive Private Deck

Come and enjoy this light-filled, beautifully maintained, three-level contemporary home complete with gardens, landscaped yard, and a children’s backyard playground.  

The main level features an open kitchen, dining, and TV/living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$0 - $0
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: 
$425 per week
Tax: State & Local: 
11.7
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Katama South Beach, 20 x 40 Heated Gunite Pool, Walk or Bike to the Beach, Luxury Home,

Stunning tri-level vacation home bordered by professionally landscaped grounds with Gunite pool, located in a quiet Katama neighborhood, walk or bike to South Beach. This spacious home is perfect for...Read more

Location: 
Katama
Sleeps: 
12
Bedrooms: 
5
Baths: 
3
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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 $17,500
July 2026
SuMoTuWeThFrSaWeek
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$17,500
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$17,500
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$17,500
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$17,500
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 $17,500
August 2026
SuMoTuWeThFrSaWeek
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$17,500
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$19,500
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$19,500
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$19,500
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$18,000
30
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September 2026
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Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Pool Heated to 82 degrees, last week of June through first week of September included in rental rate

Pool Heat to 82 degrees, first three weeks of June and last three weeks of September additional $300.      

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Long Point Beach House, All New Primary Suite, Expansive Sun Porch with Living and Dining Areas, Expansive Deck, Private Yard

This Beach-chic Long Point retreat has just undergone an update in most areas with an all-new Primary Bedroom suite and expansive sun porch hosting both living and dining areas and decorated in nautical...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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2
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$2,700
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$2,700
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$2,700
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$4,850
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 $7,000
July 2026
SuMoTuWeThFrSaWeek
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$7,000
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$7,000
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$7,000
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$7,000
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 $7,500
August 2026
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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$7,500
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$7,500
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$7,500
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 $7,500
September 2026
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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$7,500
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Stunning Greek Revival, Newly Updated, Edgartown Village Area, Walk to Fuller St and Lighthouse Beaches

Located in one of the most desirable areas of the Village center, this luxury home with its recent renovation meets the needs of today's families! A five minute stroll brings...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$0 - $0
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: 
$400 per week
Tax: State & Local: 
11.7

2 week minimum stay required

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Outstanding Tri -Level Katama Home, Pool, new 18 x 40 Heated Saltwater Pool, Bluestone Patio, Fire Pit, Walk or Bike to South Beach and 5 minute Drive to Edgartown Village Area

Beautiful tri-level contemporary home with an 18 x 40 heated saltwater pool, bluestone patio, outdoor dining area, chaise lounge chairs, and fire pit. This recently updated home includes a spacious open floor plan with vaulted ceilings, a...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
4
Baths: 
4
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$8,000
7
8
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$8,500
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$12,000
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$16,500
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30
 $17,500
July 2026
SuMoTuWeThFrSaWeek
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$17,500
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$17,500
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$17,500
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$17,500
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 $17,500
August 2026
SuMoTuWeThFrSaWeek
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$17,500
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$17,500
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$17,500
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$17,500
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$16,990
30
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 $9,800
September 2026
SuMoTuWeThFrSaWeek
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$9,800
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$9,200
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$7,500
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$7,500
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 $7,500
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Pool is heated to 84 degrees July & August &  included in the rental rate.

 

Pool heated to 84 degrees June & September, additional $450/week propane surcharge.

 

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Gracious Waterview Estate Home, Heated Pool, Hot Tub, Exclusive Eel Pond Area of Edgartown Village

Luxury Coastal Gambrel Home with Pool and Carriage House.  This Eloquent Home was designed by architect Patrick Ahearn and features waterviews of Nantucket Sound from many rooms within the house,...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
7
Baths: 
5
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$40,000
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 $40,000
August 2026
SuMoTuWeThFrSaWeek
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$40,000
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$40,000
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$40,000
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$40,000
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$35,000
30
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September 2026
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Clean Fee: 
$900 per week
Tax: State & Local: 
11.7

2 Week Minimum Stay required   

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Light Filled, Stylish Cape Home, Ideal Central Location to Vineyard Haven, Oak Bluffs, Edgartown and Public Beaches.

Sure to please, this lovely all-new custom Cape is bordered by lawn and tall oaks and features a spacious open floor plan in the main living level with a dormered...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
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: 
$380 per week
Tax: State & Local: 
11.7
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Meeting House Village Condo, Association Pool, Short Drive to Edgartown Center, South Beach & State Beach

Note: Owner is replacing Sofas seen in photos with two new slip covered sofas and will be replacing all bedding and the baths will get a primp as well. New kitchen items...Read more

Location: 
Edgartown
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$0 - $0
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: 
$275 per week
Tax: State & Local: 
11.7
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Outstanding Waterfront Home & Guest House, Panoramic Views, Beach on the Lagoon, 5 Bedrooms, 4 Baths, AC

Gorgeous Expansive Waterfront Main & Guest Cottage, perfect for a multigenerational family vacation.  Spectacular views across and up the lagoon, this pristine home and guest cottage sits on just under two...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
4
Price Range:
$0 - $0
June 2026
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July 2026
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August 2026
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$18,000
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$15,500
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 $15,500
September 2026
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$15,500
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Two Week Minimum Stay Required per Owner

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Note:  Pool is heated by solar panels so the temperature cannot be set. Generally is in the 80's during the latter part of June through the first week of September.  ...Read more

Location: 
Chilmark
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$0 - $0
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: 
$800 per week
Tax: State & Local: 
11.7
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Classic Main St Home, Stylish Updates, Beautifully Landscaped, Porch overlooks Yard, Walk to Town Center

Classic Vineyard Haven Main St Home!  Recently updated throughout and is being offered as a vacation rental, ideal for families of 6.  Multiple living spaces assure that all have room to...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
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: 
$400 per week
Tax: State & Local: 
11.7
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Classic Lovely Vineyard Cottage, Pristine Condition, Approximately 1.5 Miles to Town and Beaches. Mature Landscaped Yard, Spacious Deck

The Perfect Cozy Cottage, is pristinely maintained and situated in a quiet neighborhood just on the outskirts of Oak Bluffs.  This spacious 2 bedroom, 2 bath home sleeps 4. The...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$2,700
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$2,700
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$2,700
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$2,700
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 $3,500
July 2026
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
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$3,500
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 $4,000
August 2026
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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$4,000
30
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 $2,700
September 2026
SuMoTuWeThFrSaWeek
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$2,700
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$2,700
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$2,700
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$2,700
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30
 
Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
11.7
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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
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July 2026
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August 2026
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September 2026
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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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