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This luxuriously updated tri-level condo retreat at Quail Run in the community of homes known as Sengekontacket, has been transformed, bringing a fresh, coastal feel to every corner. The end...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$3,500 - $5,000
June 2027
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July 2027
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Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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Note: Older style TVs seen in photos have been replaced. 

This bright and classic summer cottage is ideally located just one mile from Oak Bluffs town center and all the...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$4,000 - $4,950
June 2027
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July 2027
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$4,950
August 2027
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$4,950
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$4,950
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$4,950
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$4,950
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30
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 $4,000
September 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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29
30
 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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Longview Contemporary, A/C, WiFi, Close to Lambert's Cove Beach

Tree Tops:  Tri-level contemporary home in the desirable community of Long View off of Lambert's Cove Rd, 7/10 mile to Lambert's Cove Beach. Vineyard Haven village center is a 15-minute drive from...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,520 - $4,930
June 2027
SuMoTuWeThFrSaWeek
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3
4
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$2,520
6
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$2,520
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$2,520
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$3,360
27
28
29
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 $4,620
July 2027
SuMoTuWeThFrSaWeek
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$4,620
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$4,620
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$4,620
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$4,620
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$4,930
August 2027
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$4,930
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$4,930
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$4,930
22
23
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28
$4,930
29
30
31
 $4,200
September 2027
SuMoTuWeThFrSaWeek
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2
3
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$4,200
5
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$2,520
12
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$2,520
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25
$2,520
26
27
28
29
30
 $2,520
Clean Fee: 
$475 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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$3,270
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$3,270
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$3,270
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$3,270
27
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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19
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23
24
$4,400
25
26
27
28
29
30
31
$4,800
August 2027
SuMoTuWeThFrSaWeek
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2
3
4
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6
7
$4,900
8
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14
$4,900
15
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$4,900
22
23
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27
28
$4,450
29
30
31
 $3,150
September 2027
SuMoTuWeThFrSaWeek
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$3,150
5
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$3,150
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$2,750
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$2,250
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29
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 $2,250
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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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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Lovely Contemporary Home, Quiet Location in Pond View, Private Back Yard, Porch & Deck

Beautifully maintained, family-friendly home.

Lovely 3 Bedroom, 2.5 bath home situated in a quiet enclave of homes known as Pond View and just 2.5 miles to the center of Oak Bluffs....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,700 - $4,900
June 2027
SuMoTuWeThFrSaWeek
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30
 $4,700
July 2027
SuMoTuWeThFrSaWeek
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2
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$4,700
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$4,700
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$4,700
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$4,700
25
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31
$4,900
August 2027
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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September 2027
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Lovely All Newly Furnished Home, Walk to Vineyard Haven Village Center

Perfectly located for those who love to walk! Vineyard Haven Yacht Club, Main St with its lovely shops, and the Vineyard Haven library are all within a 10-minute walk from...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,860 - $4,860
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: 
$500 per week
Tax: State & Local: 
11.7

Owner will provide Sheets & Towels additional $150. Guests can choose to bring their own linens, or rent linens. Please Inquire with agent for details. 

 

 

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Country Charm, Screened Porch, Large Yard, Bike Paths

Large families enjoy this wonderful summer home.  Conveniently located close to West Tisbury town center.  Great summer spaces for relaxing and enjoying barbeques, lawn games, lunch on the screened porch,...Read more

Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$3,600 - $4,800
June 2027
SuMoTuWeThFrSaWeek
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5
$3,600
6
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$3,600
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$3,600
20
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$3,800
27
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 $4,000
July 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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$4,800
August 2027
SuMoTuWeThFrSaWeek
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$4,800
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$4,800
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$4,800
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$4,800
29
30
31
 $3,900
September 2027
SuMoTuWeThFrSaWeek
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$3,900
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$3,900
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$3,900
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$3,900
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29
30
 $3,900
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner reduced rates for available weeks in July - see calendar for adjusted rates

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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:
$4,800 - $4,800
June 2027
SuMoTuWeThFrSaWeek
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 $4,800
July 2027
SuMoTuWeThFrSaWeek
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2
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$4,800
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$4,800
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$4,800
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$4,800
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$4,800
August 2027
SuMoTuWeThFrSaWeek
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$4,800
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$4,800
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$4,800
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$4,800
29
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31
 $4,800
September 2027
SuMoTuWeThFrSaWeek
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$4,800
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Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi

Centrally located in the Hidden Cove community of homes on the outskirts of Oak Bluffs. Lovely area to bike, walk, or play tennis at the association courts. 

The main level features an...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,400 - $4,720
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$2,400
6
7
8
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12
$3,050
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$3,050
20
21
22
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25
26
$3,200
27
28
29
30
 $4,100
July 2027
SuMoTuWeThFrSaWeek
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2
3
$4,100
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9
10
$4,100
11
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$4,300
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23
24
$4,300
25
26
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29
30
31
$4,600
August 2027
SuMoTuWeThFrSaWeek
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3
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$4,720
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$4,720
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$4,720
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$3,570
29
30
31
 $4,100
September 2027
SuMoTuWeThFrSaWeek
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$4,100
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$4,100
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$4,100
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$4,100
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 $4,100
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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Waterfront, Water View, Walk to Beach

Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $4,700
June 2027
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July 2027
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September 2027
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Clean Fee: 
$300 per week, owner will provide sheets, towels, beach towels, additional $225 per rental period
Tax: State & Local: 
11.7

Owner will provide, sheets, towels & beach towels for an additional $225 per rented period. 

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Located in the Heart of Oak Bluffs, 5 Minute Walk to OB Center and 2 Blocks to the Beach
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
2
Price Range:
$2,000 - $4,700
June 2027
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September 2027
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Clean Fee: 
$260 per week
Tax: State & Local: 
11.7
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Outstanding Edgartown Vacation Home, Spacious Coastal Decor Interior, Large Deck, Screened Porch, Just 1.5 miles to the Village Center

Chic Contemporary Farmhouse, just a short distance to Edgartown Village Center, features a quiet and private setting with all-new beach-inspired decor throughout.

The home has an open first-floor layout with the kitchen,...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$3,000 - $4,600
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: 
$550 per week
Tax: State & Local: 
11.7
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Adorable Updated 2 Bedroom 1.5 Bath Cottage, Walk to Town, Harbor and Beach

If you are looking for an adorable cottage-style home in the center of Oak Bluffs this newly updated, tastefully decorated 2 bedroom, with one full bath and a half bath, is sure to...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$2,500 - $4,600
June 2027
SuMoTuWeThFrSaWeek
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$2,600
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$2,600
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$2,800
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$2,800
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 $3,900
July 2027
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$3,900
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$3,900
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$3,900
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$3,900
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$3,900
August 2027
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$4,600
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$4,600
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 $3,100
September 2027
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$3,100
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 $2,600
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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Seaview Condominium, Waterview, Walk to Town and Beach

Beachfront Condominium with breathtaking views of Nantucket Sound. Just steps to the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$4,100 - $4,500
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: 
$275 per week
Tax: State & Local: 
11.7

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