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

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.