Historic Island Retreat on Great Diamond Island with resort like amenities!

Available starting May 1st, 2026! Stay in the original Surgeon’s Quarters on Great Diamond Island! This 2BR/2BA historic brick home blends charming details with modern updates. Enjoy wooded views from the screened porch and full access to Diamond Cove amenities: pool, fitness center, basketball court, bowling alley, 3 beaches, and more. Just a scenic ferry or water taxi ride from Downtown Portland—your perfect island escape awaits!

** Please note: furniture and décor will differ slightly from photos at time of check-in (new pictures will be updated by May 1st with new furniture and updated decor)!

Welcome to 171 Diamond, a rare opportunity to stay in the original Surgeon’s Quarters at Fort McKinley on Great Diamond Island. This beautiful 2-bedroom, 2-bath freestanding brick home blends historic details with thoughtful modern upgrades—tin ceilings, original fireplace, a gas stove, custom window treatments, and hardwood floors.

Enjoy peace and privacy from your screened-in back porch with serene wooded views. You’ll also have access to a grill and picnic table perfect for BBQs/ Inside, the home is fully furnished with tasteful decor and a fully equipped kitchen, making it perfect for a cozy week away or extended getaway.

For helpful details about the house, getting to the island, and some of our favorite local recommendations, we’ve created a welcome guidebook for our guests. It includes information about the home, island amenities, things to do on Diamond Island, and great spots to explore in Portland during your stay. If you’d like to review it before booking, feel free to send me a message and I’d be happy to share the link with you!

As a guest, you’ll have full access to all the Diamond Cove Homeowners Association amenities, including:

RA van service to and from house from Ferry/dock
Heated outdoor pool (seasonal late May-late September)
Fitness center
Indoor basketball court
Tennis & Pickleball Courts
Duckpin Bowling Alley and Game Room
Six private beaches
A playground
On-island restaurants - Diamonds Edge and Crown Jewel (seasonal)

Just 2 miles from Portland in Casco Bay, a scenic ferry ride transports you to a peaceful, car-free island with rich history, coastal charm, and natural beauty. Whether you're collecting shells at the beach, relaxing poolside, or exploring island trails, 171 Diamond offers the perfect island escape!

Getting to Diamond Island: Diamond Island is accessible by boat only. Guests can arrive via Casco Bay Lines ferry service from Portland or by private water taxi, such as Fogg’s Water Taxi. Travel times and schedules vary by season.

Please message the host before your arrival for additional details on transportation options, scheduling, and recommendations. We’re happy to help coordinate and answer any questions to make your arrival as smooth as possible.

Bedrooms/Bathrooms: Bedroom 1 features a queen bed and a private en-suite bathroom with a walk-in shower. Bedroom 2 includes 1 full sized bed and 1 twin bed. A second full bathroom with a tub is located in the upstairs hallway. All bedrooms and bathrooms are located on the 2nd floor. Portland Short Term Rental License: STHR-007450-2025