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Massachusetts | Cape Cod

Pirates Cove Estate

7 bedrooms·6.5 bathrooms·12 guests
Beach access

Set within the prestigious gated community of Oyster Harbors in Osterville, this exceptional luxury estate offers an elegant retreat surrounded by beautifully landscaped grounds. A grand driveway leads to sophisticated living spaces designed for comfort and entertaining, including a spacious living room overlooking the expansive yard, a gourmet kitchen with new appliances and dual dishwashers, a charming breakfast area, formal dining room, library, and additional lower-level media room. Thoughtful details throughout the home create an atmosphere that is both welcoming and refined, while the stately back porch provides a peaceful setting for relaxing afternoons and evening gatherings. The residence features four bedrooms and three newly renovated full baths on the second floor, along with a cozy alcove featuring a built-in twin bed. A private guest suite above the garage offers a king bedroom, full bath, sitting area, kitchenette, and laundry, while the pool house adds even more flexibility with its own bedroom, full bath, sitting area, and kitchenette. Outdoors, a heated saltwater pool and hot tub create a private oasis for relaxation and recreation. Just moments from Osterville Village and the sandy shores of Dowses Beach, this remarkable property delivers an unforgettable Cape Cod experience in one of the area's most sought-after locations.

Our promise

Satisfaction Guarantee

We've reviewed thousands of homes and approve only the best. Each one is professionally managed and vetted for comfort and style, raising the bar for every stay.

KEY Curation Notes

Oyster Harbors is one of Cape Cod's most exclusive addresses. This is a gated, private community on Grand Island in Osterville — surrounded by North Bay, West Bay, and Nantucket Sound — where the neighborhood itself sets a standard most vacation rentals can't touch.
The property functions as a private compound. The main house, a garage suite with its own king bed, kitchenette, and sitting area, and a separate pool house with a full bath and bedroom give groups multiple zones to spread out and find privacy within the same stay.
Private saltwater heated pool and hot tub, with serious outdoor space. The landscaped yard with a stately back porch is designed for lingering — morning coffee, evening entertaining, and everything in between.
The kitchen is a genuine working kitchen. Two dishwashers, a full suite of appliances including a Nespresso and a food processor, and a breakfast room alongside the formal dining area make it well-suited for groups who want to cook seriously.
2-week minimum stay, with twice-weekly housekeeping required. The owner mandates use of her cleaner during your stay at an additional cost — factor that in when budgeting. This is a 14-night minimum, not a weekly rental.
Dowses Beach and Osterville village are close, but the car is essential. The neighborhood is private and residential — you'll drive to the beach, to dinner, and into town. Plan accordingly if anyone in your group is without a car. KEY.co can arrange grocery delivery so the kitchen is stocked before you arrive.

Amenities

Indoor
TV
Air conditioning
Dryer
Internet
Washer
Outdoor
Garden/Backyard
Outdoor grill
Pool
Heated pool
Hot tub/Jacuzzi
Misc
WiFi
Beach pass
Beach towels
Hair dryer
Iron and board

Elevate your stay with add-on services

Book a home, then customize your experience. From beach gear delivery to pre-arrival groceries and private chefs, we coordinate everything you need so you can make memories in the waves and stories at sunset.

Private chef

Private chef

In-home massage

In-home massage

Beach rentals

Beach rentals

Pre-arrival groceries

Pre-arrival groceries

Alcohol delivery

Alcohol delivery

Private driver

Private driver

Bedroom details

Bedroom 1: King
Bedroom 2: Queen
Bedroom 3: Queen
Bedroom 4: Queen
Bedroom 5: King
Bedroom 6: Double + Twin
Bedroom 7: Twin

Location

Inside the destination

Neighborhood: Oyster Harbors - This grand home is located in prestigious Oyster Harbors, a gated community of Osterville, near Osterville village and Dowses beach.

Parking information

The garage is not available for use.

We're here to help

Whether you have questions on this home or want us to source other options, we're a message away!

Policies

Check-in: 4:00 PM
Check-out: 10:00 AM
Renter's age: 25+ years old
No smoking allowed
No events allowed
Pets allowed by request

Things you need to know

The pool house includes a kitchenette, full bath, sitting area, and bedroom.

Fireplaces are not for guests' use.

For stays of 2 weeks or longer only, the host requires Guests to use her cleaner twice a week during the stay.

Restrictions

Guests & Occupancy

  • Primary Guest must be 25+ and present for the entire stay; violations may result in cancellation or eviction without refund
  • Limited to stated sleeping capacity; over-occupancy may result in eviction without refund
  • Primary Guest is responsible for all damages, charges, and rule compliance; credit card on file may be charged
  • Use is limited to vacation/recreational purposes only
  • Motor homes, campers, and tents are not permitted (violation may result in termination without refund)

Events & Noise

  • Events: Weddings, parties, reunions, or large gatherings are not permitted
  • Noise compliance: Must follow all local noise and occupancy ordinances

Prohibited Activities

  • Pets: Not allowed unless pre-approved with signed addendum; non-refundable fees apply; violations may result in eviction, loss of deposit, and additional charges
  • Smoking: Strictly prohibited; Guest responsible for any odor or damage-related charges
  • Fire hazards: No campfires, fireworks, or open flames unless explicitly allowed
  • Illegal/unauthorized use: Subletting and unapproved use are prohibited
  • Unapproved modifications: Installing equipment (e.g., window A/C) or altering the space is not allowed; damage/repair costs apply

Equipment & Amenities

  • HVAC & utilities: Doors/windows must remain closed when A/C is in use to prevent damage; misuse may result in repair charges
  • Appliances & systems: Operation is not guaranteed; no refunds for malfunctions (includes A/C, internet, appliances, power outages, etc.)
  • Internet/phone/TV _(if equipped)_: Long-distance calls and paid media are charged to Guest
  • Provided items: Guests may need to bring linens, towels, and supplies unless otherwise stated; rentals may be available for a fee
  • Equipment reporting: Damage must be reported within 24 hours; unreported or excess damage beyond coverage (up to $1,000 or $300 for shorter stays) is chargeable
  • Locked areas: Restricted areas are off-limits; unauthorized access may result in charges
  • Maintenance access: Authorized personnel may enter for inspection, repairs, or showings with notice where required

Checkout & Care

  • Cleaning expectations: Must leave in clean, habitable condition; excess cleaning fees apply
  • Damage reporting: Report cleanliness or maintenance issues within 24 hours of check-in
  • Furniture & care: Return furniture to original placement; moving damage or misplacement may incur fees
  • Trash: Must be properly disposed of per instructions; excess trash removal may incur charges
  • Checkout compliance: Late checkout may incur fees up to $100 per 30 minutes
  • Keys: Lost keys incur a $60 replacement fee

Liability & Disclaimers

  • Not responsible for lost items; return shipping costs apply; unclaimed items may be discarded after 30 days
  • Not liable for injury, illness, or damage occurring during the stay
  • No refunds for non-essential failures (appliances, utilities, internet, etc.)
  • No liability for weather, pests, allergens, or natural conditions
  • Natural disasters: If uninhabitable, limited to a pro-rated refund of rent paid only
  • No refunds or relocation for nearby construction disturbances
  • Rented as-is; no refunds if expectations are not met
  • Furnishings and features may change without notice; not guaranteed
  • Errors or omissions in descriptions are not guaranteed
  • Rates & availability: Subject to change without notice