Escape to Diamond Cove Island, a tranquil oasis off Maine's coast. Discover the island's history as a military base, explore beautifully restored barracks and officer homes, and enjoy activities like pool games or duck pin bowling for all ages.
Reviews
1010 out of 10
Exceptional
Entire home
4 bedrooms3 bathroomsSleeps 102700 sq ft
Popular amenities
Washing machine
Dryer
Air-conditioning
Outdoor space
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About this property
Luxurious island home on the water, 30 minute ferry ride from Portland Maine
A Gem of Solitude and The Enchantment of Diamond Cove Island, Maine
If you live in a world of running around to the next meeting, getting kids to practice, and watching life slip by in traffic there exists a hidden gem called Diamond Cove Island, nestled off the coast of Maine, to put all that stress and tension behind. It is a place of quiet enchantment, where the serenity of nature and the charm of all around creates a spell that draws people from all corners of the world.
Your journey will start with a ferry ride from Portland where your anticipation will become palpable. As "Diamond Cove" comes into view, it casts a spell on every soul aboard. The first sight of its rugged coastline and towering trees set the stage for a unique adventure.
Diamond Cove Island is a sanctuary for nature lovers, historical adventurers, and sea glass beach combers. If you are young or young at heart there is a pool, game room, indoor basketball court an authentic duck pin bowling for everyone to enjoy. However, the picture worth a thousand words and what never gets old is the feeling you get sitting on your deck, listening to the sounds of the ocean and watching the boats rolling in and out. You can watch the lobsterman picking up their traps or waive at the people rolling in for their own adveture, it just never gets old.
For those enchanted by history, the island's history as an early 1900s military base will fill your mind with wonderment. Beautifully restored barracks, officer homes and other structures tell with visual accuracy what it was like to live and serve on the island. For the true Indiana Jones at heart the forests have artifacts and bunkers to hunt for treasures. There is even a look out structure on the property you are renting where you can envision men with telescopes triangulating the firing distance to hit their target.
Once you see all these things combined you will have no question why famous artist came to capture the play of light on the cliffs, where writers found solace in the quaint cottages, and musicians drew melodies from the whispers of the sea. Creativity thrives here.
At days end the island's locally owned restaurants offer a taste of Maine's finest. From traditional fine Maine Dining at Diamonds Edge where you can elegantly dine on the lawn or on the deck overlooking the cove or the super cool Crown Jewel bringing eclectic island vibes with its culinary expertise. If brunch is your speed the Inn has a inviting indoor or outdoor area and a fire pit where drinks can be served to truly pamper you. If you need more choices just take the ferry or call a water taxi and you are in the heart of one of Portland where choices are endless.
When you leave Diamond Cove you will be left with memories of natural beauty, history, creativity, and the pure joy of a simpler, more profound way of life. It is a story that whispers to you in months and years following the island's timeless enchantment. We invite all looking for solace and wonder to experience its magic for themselves.
Property amenities
Internet
Available in the house: WiFi
Bedrooms
4 bedrooms
Bedsheets provided
Bathroom
3 bathrooms
Bathtub or shower
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Outdoor areas
Firepit
Patio
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
Service animals only (pets not allowed)
Suitability/Accessibility
Smoke-free property
Things to do
Arcade/game room
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets not allowed (service animals are welcome, and are exempt from fees)
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
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
Property Registration Number STHR-007711-2026
About the area
Portland is home to this holiday home. Portland Head Light and Monument Square are local landmarks, and the area's natural beauty can be seen at Thompson's Point and Crescent Beach State Park. Maine Narrow Gauge Railroad and Portland Observatory are also worth visiting. Visit our Portland travel guide
Is Luxurious island home on the water, 30 minute ferry ride from Portland Maine pet-friendly?
No, only service animals are welcome at the property.
What time is check-in at Luxurious island home on the water, 30 minute ferry ride from Portland Maine?
Check-in begins at 4:00 PM.
What time is check-out at Luxurious island home on the water, 30 minute ferry ride from Portland Maine?
Checkout is at 11:00 AM.
Where is Luxurious island home on the water, 30 minute ferry ride from Portland Maine located?
Situated in Portland, this holiday home is steps from Casco Bay and within 3 mi (5 km) of Little Diamond Island and Sand Beach. Casco Bay Lines Ferry Terminal and Maine Jewish Museum are also within 6 miles (10 km).
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Luxurious island home on the water, 30 minute ferry ride from Portland Maine Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
We loved staying on Great Diamond Island. Such a beautiful and serene respite. Oliver was amazing at helping us get everything situated on the front end. And his lovely home worked perfectly for our group of 7. We explored the island, ate great food (Crown Jewel was a hit!!), and made a few trips into Portland. The hot tub was a great way to wind down each night.
Lindsey N.
Stayed 7 nights in Jul 2025
Verified
10/10 Excellent
Judith
22 Aug 2024
Liked: Cleanliness, amenities, property conditions & facilities, communication
What a fantastic vacation in Diamond Cove! Oliver’s house is gorgeous with an amazing location, views and top notch technology. The community is just perfect - isolated on a no-car island, yet just 15 minutes into Portland. Our family of 5 had a wonderful time and will definitely want to come back. Oliver was such a gracious host - even picked us up on his boat in Portland so we skipped the ferry. Amazing in every way!
The home and surroundings were beautiful. The historical setting, community pool, bowling alley, trails and Seaglass Beach kept us busy. Our biking, walking and golf cart explorations were such fun. At other times, sitting outside and watching the ferries come and go or enjoying the hot tub was all we needed. The four-year-old loved the trampoline! Our host was very responsive to any questions we had. We can see ourselves returning to the island in the future.
Let’s begin and end with the spectacular view and all the wonderful things in between.
1) Responsive and thoughtful host. He met us upon arrival to orient us to the island and house.
2) Comfortable and clean rooms.
3) Well stocked kitchen! We hosted a lobster boil with 10 people and 26 lobsters delivered to the dock thanks to the host.
4) State of the Art lights, shades and TV; strong wi-fi.
5) Hot tub!
6) Crown Jewel restaurant is a gem!
7) Explore the beaches, trails and sandbar to Little Diamond…
I can go on forever so in summary, we’ll be back!
The ideal place to kick off your shoes and relax. The golf cart was key to enjoying the property fully. Lots of trails to explore. The small beaches are typically Maine, rocky but enjoyable. The house is set up well with all you need to cook. Once you figure it out, Instacart makes grocery delivery easy. The concierges are responsive. 10/10 overall! Thank you!