Luxurious island home on the water, 30 minute ferry ride from Portland Maine

Portland, Maine
$1080 avg/night
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

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.

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Service Animals Only (pets Not Allowed)
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2700 Sq Ft (251 Sq M)
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • INTERNET

    WiFi Available
  • OUTDOORS

    Firepit Patio
  • BATHROOMS

    3 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • ENTERTAINMENT

    Arcade/game Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • Judith

    Submitted Aug 22, 2024

    Stayed Aug 11, 2024

    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!

  • Carol J.

    Submitted Oct 7, 2025

    Stayed Sep 30, 2025

    Owners are extremely supportive and responsive!

  • Jason T.

    Submitted Aug 21, 2025

    Stayed Aug 10, 2025

    Incredible location. Great home and host

  • Lindsey N.

    Submitted Jul 28, 2025

    Stayed Jul 20, 2025

    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.

  • Dianne O.

    Submitted Jun 30, 2025

    Stayed Jun 21, 2025

    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!

  • Heidi C.

    Submitted Sep 17, 2024

    Stayed Sep 7, 2024

    Our group of 7 truly enjoyed their stay at this home in Maine! Oliver really attended to every detail for us. Highly recommend!!

  • Molly L.

    Submitted Aug 9, 2024

    Stayed Jul 7, 2024

    Just an outstanding home, outstanding host, could not recommend more highly and can not wait to go back.

  • Hazel C.

    Submitted Aug 2, 2024

    Stayed Jul 25, 2024

    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!

  • Diane C.

    Submitted Jul 1, 2024

    Stayed Jun 22, 2024

    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.

Your dates are Available!

Total

Includes taxes and fees
$1,080+
View details