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5 Br Private Vacation Home Vacation Rental In Oak Bluffs, Massachusetts

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Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!

Type Private vacation home
Bedrooms 5
Bathrooms 4
House Rules
  • No pets allowed
  • Children allowed: ages 0-17
  • Smoking is not permitted
  • No events allowed;MUST be approved by Owner.
Max Occupancy 12
Host Language English
Property Id 4529589
Pirate's Reef is a NEW and beautifully decorated residence that offers 5 spacious bedrooms (2 master suites!) with 4.5 bathrooms, full finished basement with wet bar and combo pool table/table tennis, and accommodates up to 12 guests.

This is the PERFECT vacation home for you and your guests. This home is nestled behind the historic Shearer Cottage on a quiet lane in East Chop, located just minutes away from all the charm and activities that Oak Bluffs has to offer. The beach, harbor, and town are all just a pleasant 15 minute walk away, or less than a 5 minute drive/bike ride. Guests will enjoy the private, wooded area of the home's setting, allowing one to truly experience the magic of Vineyard "island living."

Each floor features 1 master suite and 1 living room, making it quite comfortable for multiple families, large groups, and entertaining. Pirate’s Reef has custom carpentry, a gas fireplace, central air conditioning, ceiling fans, a Weber gas grill, and a fire pit to help create those special memories outside. The home has blazing fast 1,000 mbps (1 gigabyte) WiFi, for when you want to stream your favorite TV shows and movies from the multiple Samsung SmartTVs throughout the home, or if you want to go live on Instagram #getawaysociety #piratesreef. The high-speed internet is ideal for those who want to “work-from-anywhere,” which in this case is the beautiful and serene island of Martha’s Vineyard.

The main level has a gourmet kitchen with a breakfast bar, a Keurig coffee maker, dishes, utensils, pots, pans, along with a gas range, and stainless steel appliances. The dining room has a large farmhouse table that seats at least 8 people. The living room has a 55” SmartTV with access to apps such as Netflix, Hulu, and Amazon Video, along with a DVD player. The main floor master bedroom has a king bed, flat screen TV, two large closets, and the bathroom has a huge walk-in shower.

The second level has 4 bedrooms. The upstairs master bedroom has a king bed, flat screen TV, and an en suite bathroom. The upstairs living room/bedroom has a sliding door and a private bath, flat screen TV, sleeper sofa, and a twin bed. The 4th bedroom has a full and twin bed and shares a Jack and Jill bathroom with the 5th bedroom, which has a queen and twin bed.

The full finished basement provides even more SPACE. Upon walking downstairs you'll immediately notice the warm hue of the hardwood floors, gray furniture, and gorgeous granite countertops on the wet bar. To top it off, the basement also contains a pool table and 65" SmartTV to ensure a good time will be had by all!

Off the living and dining room there is a wraparound deck with a Weber gas grill and outdoor seating, which provides a great environment for cookouts and gathering with friends and family. An outdoor shower enables you to rinse off after a long day at the beach. The washer and dryer is located in the unfinished basement. There is also ample parking in the driveway for 6 cars. This is a quintessential Martha's Vineyard vacation home and will exceed your expectations!

Note: The guest house above the garage is NOT part of the home rental.

Minimum age to rent is 25 years-old.

NO pets and NO smoking. Please do not move the furniture.

The cleaning fee covers cleaning, linens, towels, and the cost of laundering. Guests are subject to an additional $250 cleaning fee if grill not cleaned adequately after use.

We have consulted sources such as the Centers for Disease Control (CDC), Environmental Protection Agency (EPA), and World Health Organization (WHO). We are also implementing best practices from some of the top medical and hospitality institutions in the world to ensure we have the best cleaning and disinfecting protocols. Please rest assured that a clean home for our guests is of the utmost importance to us.

This is a Getaway Society vacation rental home. Please ask us about our portfolio of homes in Martha's Vineyard, Hilton Head, Orlando, Gatlinburg, Sandbridge Beach (Virginia), Broken Bow (Oklahoma), and the Pocono Mountains. Our vacation rental properties are perfectly located and stylishly designed to help you create an amazingly memorable experience on every single getaway. Visit our website for more information.
Oak Bluffs is home to this vacation home. Oak Bluffs Harbor and Woods Hole Ferry Terminal are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Inkwell Beach and Old Silver Beach. Traveling with kids? Consider Flying Horses Carousel and Island Cove Adventures. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and mountain biking nearby.
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    Policy

    Pet policy

    • Pets not allowed

    Check out time

    • 10:00 AM

    Check in policy

    • Check-in time starts at 4:00 pm
    • Contactless check-in available

    Payment policy

    • Localcurrency: USD

    Check out policy

    • Check-out before 10:00 am

    Know before you go

    • A car is recommended for transportation to and from this property

    Check in start time

    • 4:00 PM

    Check in instructions

    • Information provided by the property may be translated using automated translation tools
    • You will receive an email from the host with check-in and check-out instructions

    Special instructions

    • Extra-person charges may apply and vary depending on property policy
    • Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
    • Host has indicated there is a carbon monoxide detector on the property
    • Host has indicated there is a smoke detector on the property
    • Note from host: must be approved by owner.
    • Onsite parties or group events are strictly prohibited
    • Property registration number c0079082210
    • Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
    • Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
    • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
    • This property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

    Check out instructions

    • The host requires you complete the following before checking out:
    • Remove personal items, remove leftover food and drinks, and take out the trash
    • Turn off the lights and lock the doors
    • Leave the beds as is.
    • Hang wet towels and leave the others as is.
    • Wash and dry any beach towels that were used.

    Children and extra bed policy

      • Children are welcome.
    Amenities

    Popular amenities

    • Ac
    • Arcade
    • Barbecue
    • Dryer
    • Extra bed
    • Fireplace
    • Free parking
    • Heater
    • Internet
    • Kitchen
    • Laundry
    • Living area
    • Microwave
    • No smoking
    • Outdoor space
    • Patio
    • Toys
    • Tv
    • Washer
    • Washer and dryer

    Property amenities

    • Pets:
      • No pets allowed
    • Beach:
      • Beach sun loungers
      • Beach towels
    • Dining:
      • Dining table
    • Safety:
      • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
      • Deadbolt lock
      • Fire extinguisher
      • First aid kit
      • Smoke detector installed (host has indicated there is a smoke detector on the property)
    • Bedroom:
      • 5 bedrooms
      • Bed sheets provided
      • Sofa bed
    • General:
      • Smartphone
      • Unit size: 3500 sq ft (325 sq m)
    • Kitchen:
      • Blender
      • Coffee/tea maker
      • Cookware/dishes/utensils
      • Dishwasher
      • Lobster/crab pot
      • Microwave
      • Oven
      • Refrigerator
      • Stovetop
    • Laundry:
      • Laundry facilities
      • Near laundromat
      • Washing machine and dryer
    • Parking:
      • Car recommended
      • Onsite parking
    • Internet:
      • Free WiFi, with speed of 500+ Mbps (good for 6+ people or 10+ devices)
    • Outdoors:
      • Barbecue grill
      • Firepit
      • Garden
      • Outdoor furniture
      • Patio
    • Bathrooms:
      • 4.5 bathrooms
      • Bathtub or shower
      • Hair dryer
      • Soap
      • Toilet paper
      • Towels provided
    • Workspaces:
      • Computer monitor
      • Desk
      • Desk chair
      • Printer
    • Langs Spoken:
      • English
    • Things To Do:
      • Fitness facilities nearby
      • Golf nearby
      • Hiking nearby
      • Hiking/biking trails nearby
      • Marina nearby
      • Rafting nearby
      • Sailing nearby
      • Swimming nearby
      • Wildlife and game walks nearby
      • Windsurfing nearby
    • Entertainment:
      • Arcade/game room
      • DVD player
      • Hulu
      • Netflix
      • Pool or billiards table
      • Stereo
      • Streaming services
      • Table tennis
      • Video games
      • Smart TV with cable/satellite service
    • Living Spaces:
      • Dining room
      • Fireplace
      • Living room
    • Climate Control:
      • Air conditioning
      • Heating
    • Family Friendly:
      • Children's books
      • Children's games
      • Children's toys
      • Playground
    • Location Highlights:
      • Near a hospital
      • Near the bay
    • Services And Conveniences:
      • Chef
      • Iron/ironing board
      • Local meal delivery service
      • Phone
    • Suitability/accessibility:
      • Smoke-free property
 

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