Historic Island Retreat on Great Diamond Island with resort like amenities! | House in Portland
2 Bedroom House in Portland
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)!
Portland Short Term Rental License: STHR-007450-2025
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.
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
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 2 full size beds. A second full bathroom with a tub is located in the upstairs hallway. All bedrooms and bathrooms are located on the 2nd floor.
Historic Island Retreat on Great Diamond Island with resort like amenities! is located in Portland. Historic Island Retreat on Great Diamond Island with resort like amenities! provides accommodation, featuring TV, Ocean View, Oceanfront, among other amenities. This House features TV, Ocean View, Oceanfront, to make your stay a comfortable one.
Historic Island Retreat on Great Diamond Island with resort like amenities! has 2 Bedrooms , 2 Bathrooms, and max occupancy of 5 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Portland has interesting places to visit. If you want to learn more about the House in Portland, such as places to visit and things to do nearby, you can check below to learn more.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Amenities
Policies
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 long-term renters welcome onsite parties or group events are strictly prohibited property registration number sthr-007126-2025 safety features at this property include a fire extinguisher 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
FAQ's
Is this Portland house pet-friendly for guests?
Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.
Does the Portland house have a swimming pool?
Yes, this Portland house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in Portland house?
Best-rates for the Portland house starts from $315 per night with includes Fireplace/Heating, Barbecue/Outdoor Cooking, Kitchen, Air Conditioner, Pool, View, Balcony/Terrace, Bedding/Linens, TV, Ocean View, Oceanfront, Security/Safety, Wellness Facilities, Pet Friendly, Child Friendly, Internet, Laundry with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.
Is Portland house a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the Portland house wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Portland house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the Portland house?
Based on the information reported by the owner or manager, the Portland house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for Portland house?
Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
