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Waterfront 4 BR Cottage with Spectacular Views & Beach

Bedrooms 4
Property type cottage
Minimum Stay 7 nights


Minimum Stay
7 nights

About the property

Cottage, 4 Bedrooms, 2 Baths, (Sleeps 7-9)

Experience life on a small private island off the coast of Maine. Time spent on Little Diamond is like stepping back in time. No cars, traffic or hassles. Enjoy a family owned cottage, with many wonderful memories already attached. Build your own great memories when you enjoy island living at its best.

A 15-minute cruise on the Casco Bay Lines ferry brings you from Portland to Little Diamond and the Casino, the island clubhouse. A short walk takes you to the cottage. The cottage faces west to allow the very best of island sunsets, from two 40’ decks, upper and lower, to enjoy the bay view in sun or shade. A beautiful birch tree surges through both of the decks for summer shade.

The island is best enjoyed by the many footpaths that cross the island through the woods, and along the beaches, from end to end and side to side. There are no cars or trucks on the island, but there are some golf carts with island youths willing to transport you and your belongings to and from the cottage or ferry dock for a small fee.

The 100+ year old, 9-room cottage has been renovated for all the creature comforts of home without any of the headaches. A view of the bay from the front and sides of the cottage, with a beautiful birch woodland in the rear provide marvelous personal space. An outside hot & cold water (non soap) shower allows the swimmers to rinse the salt water off, located on the lower deck before coming into the cottage. Much of the furniture is original to the cottage and fits appropriately inside the home.

The two master bedrooms have Casco Bay views and double beds, and the two other bedrooms have a double-bunk bed and a triple-bunk bed. On a clear day you can see Mt. Washington, which is 90 miles away.

Tide-pooling and shelling in front of the cottage around Crab Rock is the best on the island. There is great crabbing, and terrific striper-fishing. The beach is in the front yard and depending on the tide, you may walk all the way to the next island, across a connecting sandbar, to Great Diamond Island, where there is a small country store, with treats and ice cream. Also there, is a four-star restaurant at Diamond Cove,

, where you can enjoy a fine meal, then relax on a free ferry ride back down the bay to the Little Diamond Island dock, and the cottage, or tide-willing, a nice walk across that sandbar between Great & Little Diamond islands.

There is great community spirit in the seasonal Saturday Night Suppers held at the Casino, where the island residents work together to create a wonderful meal, served family style, as you bring flatware, silverware and beverage of choice, available at the cottage. Sign up for these reasonably priced family style meals is at the Casino porch on Fridays for renters, as space is available.

This is an island where all the islanders are neighbors, and the friendly atmosphere is a pleasant reminder of yesteryear. Horseshoe pits in the backyard along the path always bring great fun and camaraderie with strolling neighbors.

Keywords: Private Island Rental, ocean view, beach front, 4 bedrooms, 2 large decks facing the bay and one other facing the walking path and woods.

More Details

Property Manager
Member since: 2010
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
March 31, 2016

Why Woody chose Portland

We have lived here on the island for over 50 years, and enjoyed every minute, raising four boys, and now they, their children and friends enjoy the cottage!

What makes this cottage unique

For all the years spent here, it somehow stays the same. Some faces change, you see family resemblances as younger generations assume the family property, and then we meet new faces who appreciate the small island living by becoming new neighbors.


5/5 -
(5 traveler reviews)

Waterfront 4 BR Cottage with Spectacular Views & Beach
average rating of 5.0 based on 5 reviews

Summer Paradise

  • 5 of 5

Stayed here for a [too short!] week with my wife and 11 year-old son, along with another couple and their boy, also 11. The house is immaculate, and has everything you could possibly need for your stay. The two main bedrooms are bright and airy, with big windows looking out over Casco Bay - it feels like you're on a cruise ship, waking up to the sound of gulls and distant lobster boats. The place is brilliant for kids - the boys just banged out the door in the morning to spend the day with new friends they met down at the ferry dock and casino, where there's a lovely little sand beach and a swimming float. They fished (caught some mackerel), gathered mussels, hunted for sea glass, climbed rocks, swam and explored and came back home when they were hungry. The islanders are very friendly and helpful - upon arrival we were greeted like old friends and lent a golf cart to take our stuff to the house (about a quarter mile or so from the ferry), and invited to the Saturday supper, where we met even more great folks who lent us bicycles for the week and gave us some pointers on what to see and do. The whole place is very laid back, and it feels like happy hour 24/7.

We day-tripped to Peaks Island where we rode bikes and had a nice lunch, walked across the sand bar to Great Diamond at low tide (another beautiful island) and took the ferry to Long Island, which has some of the best beaches in Maine, with powdery white sand and clear blue water. Portland is one quick ferry ride away, and we had memorable meals at Eventide (go around the corner to Tomasso's for a drink while you're waiting for your table!), Fore and Boone's; the Standard Bakery has great food, too. For groceries, we used Rosemont Bakery right on Commercial Street just a few steps away from the Casco Bay Ferry terminal. They're very nice folks, and they stock excellent local meat, cheese, beer and produce and can deliver to the island daily (wine too!) so you can phone in your order and never leave the island...

Which is a nice option to have. Mostly we just lounged around the house, reading and ambling along the coast, exploring the tide pools and fishing off Crab rock, cooling off with a dip at the beach right in front of the house, then enjoying a cocktail or three on the deck, which provided a postcard-perfect sunset every night. And owner Woody and his wife Doris are fantastic - they answered all our questions and paved the way for an unforgettable vacation!

  • Submitted: Jul 23, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
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0 0
Hopewell Junction, NY The mid-hudson valley

Most relaxing vacation in 20 years

  • 5 of 5

As a grandfather with two granddaughters under the age of 3 years, this was a fantastic vacation. In total, we were 5 adults and 2 toddlers for a week. It was great. The house was nicely setup, very clean, lots room, great deck and with all the Comforts of home.

We enjoyed the quite location, walks on the beach, bird watching and teaching the girls to search for sea glass.

Portland was 10 minute ferry ride away. We took advantage of few day trips to Portland and LL Bean.

Favorite spot/time was sunset on the deck, unforgettable!

Liked it so much that we booked next year before leaving the property.

  • Submitted: Dec 16, 2015
  • Stayed: Jul 2015
  • Source: VRBO, from HomeAway
Owner's Response: These wonderful guests made the most of their brief visit to Little Diamond Island. They took great care of our home, and left it as they found it. We were very pleased with their booking 2016 already and hope they return for years to come.
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1 0
Brooklyn, NY

Fantastic getaway

  • 5 of 5

We just finished our second year in a row renting this cottage, and we have absolutely loved it both times. It's great for kids, with lots of bunk beds, and two couples, with very romantic bedrooms overlooking the water. It is amazing having the beach right below, but even better is the deck perched high above it. Amazing sunsets. Wish we had never left. The owners are also fantastic to deal with.

  • Submitted: Aug 31, 2014
  • Stayed: Aug 2014
  • Source: VRBO, from HomeAway
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Needham, Mass,USA

Down home Maine at its best!

  • 5 of 5

We never realized how relaxed we could really be and how far out of the chaos of every day living we could be until we arrived at this wonderful cottage/home. The breathtaking panoramic views of the water Portland across the way and the mountains off in the distance! My husband and I were speechless, as we're our friends when they came up the following day to join us for the two weeks ( we will try next year to get more time or go up in the fall.

House has everything and more, loved it!!! Just a quick note based on one of the reviews I read we decided to go and it was a good choice but we wanted to mention that we looked everywhere for the cliffs and we're unable to locate them; found the elevation of the deck the perfect observation point to admire and watch all that surrounds us and found the proximity of the ocean to be ideal. A perfect walk down from the house...maybe two minutes from kitchen to beach, and that's with a paper plate with a tuna sandwich on it in one hand and a soda and my beach chair in the other or maybe it was a beer. But outstanding and we all thank you for our visit to your little piece of paradise. R. Sprout

  • Submitted: Apr 6, 2014
  • Stayed: Apr 2014
  • Source: VRBO, from HomeAway
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3 0
Transplanted Mainer living in Michigan

Beautiful Location, Top notch ammenities.

  • 5 of 5

This is a beautiful waterfront cottage that is large enough for big families to sleep comfortably. Everything is beautifully appointed, from the beautiful baths, to the large double beds in bedrooms with picture windows facing the gorgeous ocean view. Watch the lobstermen haul traps while you are having your morning coffee on the terrace. Pick blueberries for breakfast, lunch or dessert. Walk out 50 feet and you can harvest fresh mussels for dinner. You may have luck with crabbing or fishing. Lobsters can be had at Great Diamond - just a short walk across the sandbar at low tide. It is all there. Maine at its very best. This home has been lovingly decorated and is quintessential Maine. Very lovely, very comfortable, very quiet. A large deck with wraparound seating and roomy picnic table overlooks the water. Could not have found a better place to stay. One note: this location will require constant watchful monitoring of very young children, due to the nearby cliffs, the height of the deck, the proximity of the ocean and the fragile nature of some furnishings. Was perfect for our passel of 10-15 year olds. No issues, no problems and much joy. Thanks for everything.

  • Submitted: Aug 4, 2012
  • Stayed: Jul 2012
  • Source: VRBO, from HomeAway
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7 0


Nearest Ferry
1 Miles
Casco Bay Lines
Nearest Beach
15 Metres
Car: not necessary


Rates & Availability

Little Diamond Island Landing Cottage Rental Rates

Rental Basis:
per property
Manager accepts payment in:
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Rate Period Nightly Weekend Night Weekly Monthly * Event
My Standard Rate
7 night minimum stay

Additional information about rental rates

Pet Fee $150
Enter dates for accurate pricing
Available arrival
Available stay (no arrival)
Calendar not updated in over 2 months and may not be available. Look for rentals with Request to Book or updated calendars.


Little Diamond Island Landing Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
Location Type:
  • Beach View
  • Beachfront
  • Mountain View ...
  • Ocean View
  • Oceanfront
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Air Conditioning ...
  • Clothes Dryer
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Telephone ...
  • Towels Provided
  • Washing Machine
  • Wood Stove ...
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Kitchen
  • Microwave
  • Oven ...
  • Refrigerator
  • Stove ...
  • Toaster
  • Dining
  • Dining Area
  • seating for 8 people
  • 2 Bathrooms
  • Shower on lower deck - outdoor shower , Please do not use soaps, shampoos and the like
    Bathroom - 2nd floor - toilet , combination tub/shower , raised tub / shower to aide in bathing children
    Bathroom 1st floor - toilet , shower , includes clothes washer & dryer
  • 4 Bedrooms, Sleeps 9
  • Teddy's Bedroom - 1 double , Picture window with views across the bay
    Fan Bedroom - 1 double , Picture window with views down the bay, TV on wall
    Boy's Bedroom - 1 bunk bed , Double bunk bed with views to Portland
    Triple Bedroom - 1 bunk bed , Tri-level bunk bed with views to Falmouth and back to woods
  • Double Beds (2), Bunk Beds (2)
  • Books ...
  • CD Player
  • DVD Player
  • Games ...
  • Satellite / Cable ...
  • Stereo
  • Television ...
  • VCR
  • Video Library
  • Boat ...
  • Deck / Patio ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters ...
  • children welcome
  • non smoking only ...
  • pets considered ...
  • cinemas
  • marina
  • museums
  • restaurants
  • ruins
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • horseshoes
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • groceries
  • hospital
  • laundromat
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • hiking
  • kayaking
  • mountain biking
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surf fishing
  • swimming
  • tennis

Partner Offers

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