Entire home

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

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Interior
Property grounds
Property grounds
Property grounds
Exterior

Reviews

10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 10250.8 sq m

Popular amenities

  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space

Explore the area

View map
Portland, ME
  • Place, Little Diamond Island
    ‪5 min drive‬
  • Place, State Theatre
    ‪31 min drive‬
  • Place, Thompson's Point
    ‪34 min drive‬
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)
    ‪38 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 2

1 Queen Bed

Bedroom 3

2 Double Beds

Guest House Bedroom

1 Queen Bed

Primary Bedroom

1 King Bed

3 bathrooms

1st Floor Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Guest House Bathroom

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Primary Ensuite Bath

Soap · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio

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.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed, service animals permitted
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Smoking

Smoking is not permitted

Important information

You need to know

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
Property Registration Number STHR-006009-2024

Frequently asked questions

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.

How much does it cost to stay at Luxurious island home on the water, 30 minute ferry ride from Portland Maine?

As of 3 Apr 2026, prices found for a 1-night stay for 2 adults at Luxurious island home on the water, 30 minute ferry ride from Portland Maine on 19 May 2026 start from AU$971, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 10 out of 10 reviews
Rating 8 - Good. 0 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jason T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Incredible location. Great home and host
Stayed 7 nights in Aug 2025
Response from VrboOwner on 7 Oct 2025
Great guest and a pleasure to have. Welcome anytime
Verified

10/10 Excellent

Carol J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Owners are extremely supportive and responsive!
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

Molly L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The BEST Home

Just an outstanding home, outstanding host, could not recommend more highly and can not wait to go back.
Stayed 8 nights in Jul 2024
Response from VrboOwner on 9 Aug 2024
Thanks Molly. Very happy you enjoyed your stay and look for ward to seeing you again soon!
Verified

10/10 Excellent

Lindsey N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Incredible Stay!

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.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 28 July 2025
Thanks Lindsey. Very happy you all had a great time and look forward to welcoming you back!
Verified

10/10 Excellent

Heidi C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing setting!

Our group of 7 truly enjoyed their stay at this home in Maine! Oliver really attended to every detail for us. Highly recommend!!
Stayed 7 nights in Sep 2024
Response from VrboOwner on 17 Sept 2024
Thank you Heidi! Look forward to having you back!
Verified

10/10 Excellent

Judith

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!
Stayed 6 nights in Aug 2024
Verified

10/10 Excellent

Dianne O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous Property/Attentive Owners

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!
Stayed 7 nights in Jun 2025
Response from VrboOwner on 28 July 2025
Pleasure to have you and you are welcome back anytime!! Thanks Oliver
Verified

10/10 Excellent

Diane C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Diamond Cove-Portland Maine

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.
Stayed 6 nights in Jun 2024
Response from VrboOwner on 19 July 2024
Thank you again Diane. You and your family were a pleasure to meet and fills me with happiness that you enjoyed your stay and the island. Hope to see you again next year! It is a great tradition for your grandson to experience!!
Verified

10/10 Excellent

Hazel C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Worth a visit, worth a lifetime…

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!
Stayed 8 nights in Jul 2024
Response from VrboOwner on 9 Aug 2024
Hi Hazel. Thanks so much for the kind words and glad you enjoyed the island as much as we do. It is a special place unlike any other. You and your family are welcome any time!
Verified

10/10 Excellent

Ann F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Jun 2025
Response from VrboOwner on 7 Oct 2025
Amazing guest and thanks for the kind words on the home!

About the host

Hosted by Oliver Pennington

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