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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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Spectacular, Edgartown Village Luxury Home, Heated Pool, Pool House, Multiple Family Living Spaces

A luxurious retreat, architect-designed and renovated Colonial home featuring outstanding outdoor living space with heated Gunite pool, surrounded by a large bluestone patio, multiple areas to relax, and a pool...Read more

Location: 
Edgartown
Sleeps: 
12
Bedrooms: 
6
Baths: 
7
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$20,000
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$20,000
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$20,000
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$25,000
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 $32,000
July 2026
SuMoTuWeThFrSaWeek
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$32,000
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$32,000
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$32,000
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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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$32,000
30
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September 2026
SuMoTuWeThFrSaWeek
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$25,000
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$15,000
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$15,000
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 $15,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Pool heated To 82 in July and August
All other weeks pool heat is $400 per week

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Sweet Updated 3 Bedroom Home, Nicely Tucked in Lightly Wooded Area, Central Location, Beaches and Towns just a short Drive!

Lovely reverse contemporary home with a large deck, outdoor dining, and grill area. The upper level of this home features an open kitchen, living, and dining area stylishly furnished.  Nicely equipped kitchen...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
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$4,000
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29
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 $4,000
July 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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27
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30
31
 $4,000
August 2026
SuMoTuWeThFrSaWeek
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$4,000
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3
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$4,000
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$4,000
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$4,000
23
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$4,000
30
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 $4,000
September 2026
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$3,500
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$3,500
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 $3,500
Clean Fee: 
$300 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
SuMoTuWeThFrSaWeek
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$18,000
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$18,000
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$18,000
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$15,500
30
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 $15,500
September 2026
SuMoTuWeThFrSaWeek
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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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Adorable 2 Bedroom, 1 Bath Cottage, Large Private Back Yard, Deck, Walk to Vineyard Haven Center

Adorable light-filled cottage, with modern furnishings, this lovely 2 bedroom home is situated on a large lot on a quiet street just on the outskirts of Vineyard Haven Center.  The home has a...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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2
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 $4,900
July 2026
SuMoTuWeThFrSaWeek
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$4,900
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$4,900
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$4,900
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$4,900
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 $5,900
August 2026
SuMoTuWeThFrSaWeek
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$5,900
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$5,900
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$5,900
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$5,900
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$4,900
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 $4,900
September 2026
SuMoTuWeThFrSaWeek
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$4,900
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$4,900
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Clean Fee: 
$450 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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Quintessential West Chop Waterfront Home. Private Beach, Spectacular Views

Enjoy the essence of summer at this waterfront home with a private beach just 50 yards in front of the house. Evenings enjoy the magnificent sunsets while relaxing on the...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$25,000
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 $28,000
July 2026
SuMoTuWeThFrSaWeek
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$28,000
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$25,000
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$25,000
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$25,000
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 $28,000
August 2026
SuMoTuWeThFrSaWeek
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$28,000
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$28,000
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$28,000
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$28,000
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$28,000
30
31
 $25,000
September 2026
SuMoTuWeThFrSaWeek
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2
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5
$25,000
6
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$17,500
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$17,500
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$17,500
27
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29
30
 $17,500
Clean Fee: 
$800 per week
Tax: State & Local: 
11.7
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Newly update mid-century modern beach house set in the private community of homes surrounding Sengekontacket pond. The cozy summer cottage offers indoor and outdoor living at its best with a...Read more

Location: 
Oak Bluffs
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
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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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29
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 $3,500
July 2026
SuMoTuWeThFrSaWeek
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2
3
4
$3,500
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$3,500
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$3,500
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$3,500
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27
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30
31
 $4,000
August 2026
SuMoTuWeThFrSaWeek
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$4,000
2
3
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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
27
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29
30
 
Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
11.7
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Pristine Cape, Located on a Large Lot in Bold Meadow Area of Edgartown, Large Yard, Sleeps 8

The perfect vacation home sits on a large lot with a beautifully landscaped private yard bordered by woodlands.  Bold Meadow is a lovely private enclave of homes on the outskirts of...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
3
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: 
$525 per week
Tax: State & Local: 
11.7
Add Favorite
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Charming Oak Bluffs Home, Waterfront on the Lagoon, Patio & Deck Areas. Spectacular Views & Sunsets

Waterfront on the Lagoon! The highlight of this home is its breathtaking views across the lagoon and beautiful sunsets. Whether you're inside or outside on the deck or patio, you can...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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2
3
4
5
6
$5,000
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13
$5,000
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$5,000
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$5,000
28
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 $7,400
July 2026
SuMoTuWeThFrSaWeek
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2
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4
$7,400
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$7,400
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$7,400
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$7,400
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30
31
 $8,500
August 2026
SuMoTuWeThFrSaWeek
 1
$8,500
2
3
4
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8
$10,500
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$10,500
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$11,500
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
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$5,000
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
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Edgartown, Katama Area, Spacious Luxury with Designer Detailing, Chef's Kitchen, Multiple Living Spaces, 4 Bedrooms, 3.5 Baths

New in 2022 large addition and full renovation to this beautiful Katama home. Located within walking distance of town (1.4 miles) and biking to Katama South Beach (2.1 miles). 

The...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
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: 
$550 per week
Tax: State & Local: 
11.7

Sales Tax Exempt for weeks 8/8 & 8/15

 

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Hart Haven, Spacious Contemporary Colonial, Private Association Beach .8 mi from house, Private Association Tennis, 5 min walk from house

Located in the desirable enclave of homes known as Hart Haven just on the outskirts of Oak Bluffs Center, rental guests will surely enjoy this beautifully maintained home bordered by...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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$10,000
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 $10,000
July 2026
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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$10,000
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 $10,000
August 2026
SuMoTuWeThFrSaWeek
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$10,000
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$11,000
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$11,000
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$11,000
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 $10,000
September 2026
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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$10,000
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 $10,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Heated Pool, 10 x 16. Edgartown Village Center, Walk to Town, Sleeps 6, South and State Beaches 10 to 12 minute drive.

Beautiful new in-town home with heated pool,screened porch, a lovely, landscaped yard with expansive lawn area and nicely tucked on a quiet street just a 10-minute walk from the Edgartown...Read more

Location: 
Edgartown
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: 
$600 per week
Tax: State & Local: 
11.7

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