Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi

MVVR EXCLUSIVE:  Classic, beach cottage with spectacular views across the sound, calm water swimming, and a great area for kayaking. The open kitchen, dining, and living areas are enhanced by the wall of windows...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
1
Price Range:
$2,000 - $3,200
June 2027
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$2,250
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$2,300
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$2,700
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$2,900
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 $3,250
July 2027
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$3,250
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$3,250
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$3,250
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$3,250
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$3,350
August 2027
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$3,400
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$3,400
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$3,400
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$3,200
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 $2,000
September 2027
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$2,000
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 $2,000
Clean Fee: 
$325 per week
Tax: State & Local: 
14.45

Cottage books Tuesday to Tuesday July & August weeks

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ALVEN

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Property Details
Spacious Oak Bluffs Home, Heated Pool 16 x 32, 4 bedrooms & 3.5 baths sleeps 8

This charming and spacious 4-bedroom, 3.5-bath home offers multiple living areas, including a main living room with TV, a cozy sitting room, and a lower-level family room featuring a TV,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$0 - $0
June 2027
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Clean Fee: 
$550
Tax: State & Local: 
14.45
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BURBS~

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Property Details
Set Just on the ouskirts of Oak Bluffs. Central AC, Screened Porch

Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs center and beach area.  Fully furnished screen porch and shady porch.  This lovely home sleeps families of 8 comfortably.

The main...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$0 - $0
June 2027
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$6,500
August 2027
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Clean Fee: 
$475 per week
Tax: State & Local: 
14.45
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ST203

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Property Details
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:
$0 - $0
June 2027
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Clean Fee: 
$275 per week
Tax: State & Local: 
14.45
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ST304

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Property Details
Sea View Condominium, Water View, Walk to Town & Beach-Across the Street

Sea View Condominium with a breathtaking view of Nantucket Sound from almost every room. Just steps from the beach.Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$0 - $0
June 2027
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Clean Fee: 
$275 per week
Tax: State & Local: 
14.45
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MILTD

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Property Details
Perfect in Town Location. Just 1 to 2 blocks to Beach, Town Center & Harbor Area, Walk to and from the Ferry

Centrally located in the heart of Oak Bluffs, walk 1-2 blocks to the beach, public tennis courts, and town & harbor areas. This wonderful large home has a large wrap-around porch for relaxing, 7...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
7
Baths: 
3
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSaWeek
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$9,500
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$9,500
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$9,500
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$9,500
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 $13,500
July 2027
SuMoTuWeThFrSaWeek
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$13,500
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$13,500
August 2027
SuMoTuWeThFrSaWeek
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$13,500
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$13,500
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$13,500
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 $12,500
September 2027
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$12,500
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$12,500
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$12,500
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$12,500
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 $12,500
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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ALLER

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Property Details
Oak Bluffs 4 Bedroom Home, Walk to Town & Beach!

10-minute walk to Oak Bluffs center and beach area from this lovely modern vacation home.  Enjoy all that the summer community of Oak Bluffs has to offer with quaint shops,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSaWeek
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$3,680
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$3,680
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$3,680
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$3,900
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 $5,250
July 2027
SuMoTuWeThFrSaWeek
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$5,250
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$5,250
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$5,250
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$5,250
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$5,250
August 2027
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$5,750
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 $4,500
September 2027
SuMoTuWeThFrSaWeek
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$4,500
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$4,200
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$4,200
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$4,200
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 $4,200
Clean Fee: 
$475 per week
Tax: State & Local: 
14.45
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ROLAJ

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Property Details
Waterfront, Water View, Lagoon Beach

This charming, recently renovated, waterfront home atop the lagoon bluffs, boasts spectacular sunsets and panoramic waterfront views of the Lagoon, outer Vineyard Haven Harbor, and Cape Cod from patios, living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2027
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Clean Fee: 
$250 per week
Tax: State & Local: 
14.45
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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:
$0 - $0
June 2027
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Clean Fee: 
$480 per week
Tax: State & Local: 
14.45
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FISHJ

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Property Details
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 2027
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 $6,900
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$6,900
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 $6,900
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$5,200
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$5,200
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 $5,200
Clean Fee: 
$425 per week
Tax: State & Local: 
14.45
Add Favorite
 
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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:
$0 - $0
June 2027
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Clean Fee: 
$480 per week
Tax: State & Local: 
14.45

 

 

 

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LIJOY~

Inquire
Property Details
Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, Bike Paths at Entrance to Neighborhood, Multiple Beaches Near By

Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSaWeek
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 $6,800
July 2027
SuMoTuWeThFrSaWeek
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$6,800
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$7,200
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$7,000
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$7,000
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$7,300
August 2027
SuMoTuWeThFrSaWeek
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$7,300
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$7,800
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$7,800
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$7,300
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 $6,800
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SuMoTuWeThFrSaWeek
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$6,800
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$7,000
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29
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Clean Fee: 
$420 per week
Tax: State & Local: 
14.45
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TRAVM

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Property Details
Updated East Chop Area Summer Retreat, Great Proximity to Town Center and Beaches, Cottage Styling with All the Modern Amenities, Central A/C. Covered Porch and Open Patio Areas.

Visitors will enjoy this delightful &  comfortable 4 bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. 

Relax in the breeze with your morning coffee on the front...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2027
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 $5,350
July 2027
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$5,350
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$5,350
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$5,350
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$5,350
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$7,000
August 2027
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$7,000
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$7,200
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$7,500
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$7,500
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September 2027
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Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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TERSM

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Property Details
Modern, Newly Renovated, Architecturally Significant Beach Cottage Design. Close to Town and Beaches, Tucked in the Lovely Community of Summer Homes, Waterview Farms!

Gorgeous all newly renovated and newly furnished mid-century beach cottage, now a modern vacation oasis designed by the prominent interior design firm, - Tersigni Palachek. This eloquent, yet beachy home offers...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,900
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$3,900
27
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 $6,400
July 2027
SuMoTuWeThFrSaWeek
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$6,400
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$6,400
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$6,400
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$6,400
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$6,400
August 2027
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$7,200
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$7,200
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$7,200
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$7,200
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 $7,200
September 2027
SuMoTuWeThFrSaWeek
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$7,200
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$2,700
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$2,700
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$2,700
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 $2,700
Clean Fee: 
$425 per week
Tax: State & Local: 
14.45

Owner books Fri to Fri July & August weeks!

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MAHAB

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Property Details
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 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: 
$300 per week
Tax: State & Local: 
14.45

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