The Black Pearl: Oyster Harbors on Private Beachfront Estate with Deepwater Dock

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Last updated: 09/01/2015
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:7 nights
  • Internet:Yes
  • Pets considered:Yes
  • Wheel chair accessible:No

Property description

Welcome to what we affectionately refer to as “The Black Pearl”, a vintage home located at one of the Cape's most coveted locations in Oyster Harbors! This charming cape home is in the prime location facing Sampson’s Island, Cotuit Bay, and Martha’s Vineyard. Beautiful sunrises, sunsets, and prevailing winds keep the temperature just perfect and the bugs afar. Deep water dock with access to fast water in minutes. Boat available for qualified boaters. Six bedrooms of which three are water front. (Beds for 12: 1 king, 1 queen, 2 full, and 4 twins). Three full baths, 1 half bath and outside shower.

About the Location: Oyster Harbors is a private island that is only accessible to its residents, club members or registered guests. Only the owners or house managers can register guests for access. Admittance is extremely exclusive, time and date sensitive. Please inform house manager or owners of any guests that will be going to the residence during the rental stay.

About the Home: The Black Pearl is a vintage home that will be under renovation during the winter months for the next several years updating the physical condition of the property. While under renovation, the rental price cannot be beat and is below market based upon the home's coveted location. Guests will enjoy the beautiful sunrise, sunset, prevailing winds and sights of Martha’s Vineyard and Nantucket Sound from nearly every vista.

Though at first appearance the house is a bit timeworn, the charm of the home will overshadow its tattered exterior. The furnishing inside are impeccably maintained, in pristine condition and immaculate All linens are freshly pressed with quality duvets and pillows. Plenty of beach towels with Samson’s Island a quick swim, paddle board or kayak ride away.

See Amenities page for boat charter and kayak/paddle board rentals!

Check-In Time: 4:00 pm
Check-Out Time: 11:00 am

Minimum stay is 7 nights, however shorter stays will be considered with potentially higher rates. Please inquire with the owner directly.

Security Deposit: $2,500.00 ($3,000 with pre-approved pets)

Cleaning Fee: $750.00

Pets: By exception only

Maximum Occupancy: 12 people

Concierge Services:
• Daily housekeeping and laundry service available at $35.00 per hour - $50.00 minimum. One two hour visit required for every three day stay. Payment for scheduled housekeeping will be collected in advance of stay - 48 hour notice required
• Grocery delivery – provide your list and will be delivered to the home within 4 hour window of request - 48 hour notice, payment in advance
• Special California Wine Selections Available (Owners are from California and reside 30 minutes from Napa Valley), payment in advance
• Daily Errands - $35.00 per hour with 48 hour notice, payments in advance

June, September, and off season rentals require a daily housekeeping fee of $50 a day.

Rate: $25,000 for the weekend
Security Deposit of $20,000 required
12 Guests Maxium


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Property Type

  • House
  • 5000 sq. ft.

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals

Onsite Services

  • Car Available


  • Events Allowed
  • Long-Term Renters Welcome
  • Children Welcome
  • Non Smoking Only
  • Pets Considered:

    Pets considered on an individual basis upon owner approval. (Security deposit changes to $3,000 with pre-approved pets). If for a special event contact owner directly for pricing in addition to wedding security deposit....moreless

  • Wheelchair Inaccessible

Bedrooms: 6 Bedrooms, Sleeps 13, Beds for 12-13

  • Bedroom 1: 1 king


  • Bedroom 2: 1 queen


  • Bedroom 3: 3 twin/ single


  • Bedroom 4: 2 twin/ single


  • Bedroom 5: 1 queen


  • Bedroom 6: 1 queen


  • The bedrooms are set up wonderfully for a large family with children. The boys can have a room to themselves and the girls can have their privacy as well with twin beds galore. The individual adult rooms can accommodate 4+ couples...there is plenty of room for everybody....moreless

Bathrooms: 3 Bathrooms, 1 Half Bathroom

Other Amenities

  • Boat Charters: Cocktail cruises, site seeing or fishing charters on a 60 Viking or 32 foot regulator are available with catered snacks, meals, and beverages. Visit Martha’s Vineyard, Nantucket or Newport for a lunch, dinner or short day trip. Boat charters must be paid for in advance and are only refundable due to weather cancellations. Hourly Rate – minimum of two hours 60’ Viking: $800.00 per hour 32’ Regulator: $400.00 per hour Paddle Boards and Kayaks: Home comes with 1 paddle board and 2 kayaks. Additional equipment can be rented upon request. Lost or damaged equipment will be deducted from security deposit ...moreless


  • Books
  • DVD Player
  • Game Room
  • Satellite / Cable
  • Stereo
  • Television
  • Toys


  • Away From It All
  • Family
  • Sports & Activities


  • Churches
  • Cinemas
  • Health/Beauty Spa
  • Library
  • Marina
  • Museums
  • Restaurants

Local Services & Businesses

  • ATM/Bank
  • Fitness Center
  • Groceries
  • Hospital
  • Medical Services

Leisure Activities

  • Antiquing
  • Beachcombing
  • Bird Watching
  • Boating
  • Paddle Boating
  • Shelling
  • Sight Seeing
  • Walking
  • Wildlife Viewing

Location Type

  • Beach View:

    You have your own private beach, and an entire barrier island just 100 yards off your dock....moreless

  • Beachfront:

    This property is without a doubt the BEST location in Oyster Harbors. It is situated on the beach with views galore....moreless

  • Ocean View:

    Amazing views of Martha's Vineyard and Nantucket ....moreless

  • Oceanfront:

    This home has its own deep water dock....moreless

  • Resort:

    Located 1.5 miles from Wianno Yacht Club....moreless

  • Village:

    The village of Osterville is one of the Cape's best kept secrets - its maybe 2 miles from this home....moreless

  • Water View:

    The sun sets right over Cotuit Bay...moreless

  • Waterfront:

    Walk across the private lawn onto some of the best beaches in the cape....moreless

Sports & Adventure Activities

  • Cycling
  • Deepsea Fishing
  • Fishing
  • Golf
  • Kayaking
  • Pier Fishing
  • Sailing
  • Ski Privileges Optional
  • Snorkeling
  • Sound/Bay Fishing
  • Surf Fishing
  • Swimming
  • Tennis
  • Water Skiing
  • Water Tubing
  • Wind-Surfing


  • Dining:

    There are abundant areas to eat indoors or outdoors....moreless

  • Dining Room
  • Seating for 10 people


  • Clothes Dryer
  • Fireplace
  • Internet
  • Linens Provided
  • Living Room
  • Parking
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wood Stove


  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove


  • Boat
  • Deck / Patio
  • Golf
  • Kayak / Canoe
  • Lawn / Garden
  • Outdoor Grill
  • Tennis
  • Water Sports Gear


Write a review 5
from 1 traveler reviews
Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
Early summer
Jun 1 - Jun 30, 2016
7 night min stay

Summer 2016
Jul 1 - Sep 5, 2016
7 night min stay

My Standard Rate
7 night min stay


Additional information about rental rates

Fees and Rental Conditions:

  • Property Damage Protection $99
  • Cleaning Fee $750
  • Refundable Damage Deposit $2,500
  • Taxes Not included


Usage of the boat is subject to appropriate renter and qualifications. Renter must have appropriate insurance.

Cancellation policy:

100% refund if canceled at least 30 days before arrival date.

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Last updated: 09/01/2015
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates


75 Miles
Nearest Airport
Logan, Boston International Airport
2 Miles
Nearest Barpub
10 Miles
Nearest Ferry
Hyannis, MA
1 Miles
Nearest Golf
Oyster Harbors Golf Club
10 Miles
Nearest Train
Hyannis, MA
10 Miles
Nearest Motorway
Rte 6
2 Miles
Nearest Restaurant
Wimpy's Seafood Market
Nearest Beach
Private Beach

Car: Not Necessary

An ideal Cape Cod location, featuring all of the breathtaking views you can ask for. The house is large and can accommodate 12 sleeping in beds. Water sports, activities, and 'toys' are available as well. This is a family home and we want you to feel at home when you are here.


Owner info

Why the Owner Chose Osterville:
Get lost with the views, relax in a rocker on the porch, and watch your life slow down and appreciate life's simple pleasures and natural beauty.

The Unique Benefits at this House:
You cannot beat the location of this property and the surroundings. You have year round beach front access, a deep water dock, unobstructed views, and plenty of room for all the family and friends. The landscaped lawn and gardens are perfect for a special occasion or event. See Amenities section for Boat Charters, Paddle Boards, and Kayak Rentals info.

Contact us

Speaks: english



VRBO #503534

This listing was first published here in 2013.

Date last modified - Monday, November 30, 2015

Minimum stay: 7 nights
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Member since: 2013
Speaks: english
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  • Response time Within a few days
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  • Calendar last updated 09/01/2015

+01 4157972544

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The Black Pearl: Oyster Harbors On Private Beachfront Estate With Deepwater Dock

Osterville #503534

6 BR  3.5 BA  Sleeps 13

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