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Grand Island Villa

5 bedrooms·6.5 bathrooms·12 guests·6,500 sq/ft

Designed for elevated coastal living, this expansive estate offers an exceptional blend of privacy, comfort, and resort-style amenities within the secure gated community of Grand Island. Thoughtfully crafted for entertaining and relaxation, the home features soaring two-story ceilings, beautifully designed gathering spaces, and a seamless indoor-outdoor flow. The gourmet kitchen opens effortlessly into the dining and living areas, while French doors lead to a stunning backyard retreat complete with a heated pool, basketball court, clay tennis court, and lush landscaped grounds. Whether enjoying a spirited tennis match, gathering around the outdoor fireplace, or unwinding poolside, every detail of this property is designed to create unforgettable moments. The spacious layout includes multiple private suites and flexible living spaces ideal for families and groups. The first-floor primary suite offers a spa-inspired bath and dual walk-in closets, while additional ensuite bedrooms provide comfort and privacy throughout the home. A separate guest sanctuary above the detached four-car garage includes its own living area and kitchenette, creating the perfect private escape for visitors. Located near Cape Cod attractions, island ferries, beaches, and dining, this remarkable retreat combines luxury, recreation, and convenience in one extraordinary setting.

Our promise

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KEY Curation Notes

Over 6,000 square feet across two buildings within the gated enclave of Oyster Harbors on Grand Island — one of Cape Cod's most exclusive private communities, accessible only through a manned gatehouse. The setting is wooded, immaculately private, and quiet in a way that open-waterfront properties simply aren't.

Private heated pool in a secluded fenced yard, private clay tennis court, and an adjacent half basketball court — the recreational amenity depth here is unusual. The pool area is surrounded by manicured grounds with a pergola, lounge space, and gas grill; French doors from the dining room open directly to it.

A detached garage apartment adds meaningful separation for large groups — above the four-car garage, a private suite with king bed, en-suite bath, full wet bar, sectional lounge, and game table functions as a self-contained space. Ideal for grandparents, adult children, or a second couple wanting their own entrance and living area.

Five en-suite bedrooms plus a formal bar and cocktail room in the main house — the king primary suite on the main floor has river-stone walk-in shower, soaking tub, his-and-hers vanities, and two walk-in closets. The upstairs bedrooms each have private baths. A dedicated office on the main floor is a genuine convenience for anyone working remotely.

No beach on the property — Oyster Harbors' community beaches and the Oyster Harbors Club (membership required for golf) are the nearby amenities. Dowses Beach is about 2.5 miles away; Osterville Village shops and dining are a short drive.

Pool is seasonal and not guaranteed outside peak summer months — subject to routine maintenance and testing. Confirm availability for shoulder-season stays.

Amenities

Indoor

Air conditioning

Dryer

Internet

Washer

Outdoor

Garden/Backyard

Outdoor grill

Pool

Heated pool

Deck

Misc

Crib

Linens

Satellite / Cable

Towels

Vacuum

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

In-home massage

Beach rentals

Pre-arrival groceries

Alcohol delivery

Private driver

Bedroom details

Bedroom 1: King

Bedroom 2: King + Two Twins

Bedroom 3: Queen

Bedroom 4: Two Twins

Bedroom 5: King

Location

Inside the destination

Neighborhood: Oyster Harbors - Situated within the secure gated community of Grand Island. This home is located in a truly peaceful, private setting conveniently located next to Cape attractions, Island ferries and splendid restaurants.

Parking information

A detached four-car garage is available.

Reviews

David B.

Comfortable property that accommodated the whole family with activities, space to spread out, and comfort.

Policies

Check-in: 4:00 PM

Check-out: 10:00 AM

Renter's age: 25+ years old

No smoking allowed

No events allowed

No pets

Things you need to know

Pool use is seasonal, not guaranteed outside peak summer months, and subject to routine testing and maintenance.

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