A calm sea with a sailboat and rocky coastline.

Great Diamond Island Holiday Rentals

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Our top choices for Great Diamond Island holiday rentals

Cozy and charming coastal retreat

Cozy and charming coastal retreat
West Point
9.8 out of 10, Exceptional, (31 reviews)
"My family and I had an amazing time at the schoolhouse. It is much bigger than the pictures show! Great beds, the couches will force you to nap, and we had so much fun exploring the area. They had everything you need for fun at the beach, and lots of options for kids to keep busy. Highly recommend!"
United Kingdom
Byrony S.
The price is AU$862
includes taxes & fees
23 Aug - 24 Aug
Cozy and charming coastal retreat

Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is AU$442
includes taxes & fees
3 Aug - 4 Aug
Mid Coast Getaway w/ water views

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (61 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is AU$508
includes taxes & fees
6 Aug - 7 Aug
Camp Forever cottage

Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (65 reviews)
"Great spot to relax and enjoy the beautiful outdoors. Very quiet and amazing views of the water. Everything needed for a comfortable and relaxing getaway. Highly recommend if coming to the area! "
United States
Erin
The price is AU$670
includes taxes & fees
2 Aug - 3 Aug
Centerview cottage

Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (11 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
Orchid Harbor, Bailey Island 3BR

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (57 reviews)
"Wonderful stay!"
United States
Erika T.
The price is AU$526
includes taxes & fees
29 July - 30 July
Full sized home

Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....
United States
Lisa E.
The price is AU$1,248
includes taxes & fees
27 July - 28 July
Three bedroom in United States of America, Freeport

Coastal Waterfront Retreat with Sauna, Kayaks & Fire Pit, Freeport, Near LL Bean

Coastal Waterfront Retreat with Sauna, Kayaks & Fire Pit, Freeport, Near LL Bean
Freeport
9.8 out of 10, Exceptional, (20 reviews)
"Very relaxing and quiet. Hosts were very accommodating "
United States
Heidi T.
The price is AU$2,084
includes taxes & fees
10 Aug - 11 Aug
Coastal Waterfront Retreat with Sauna, Kayaks & Fire Pit, Freeport, Near LL Bean

Private Waterfront Estate in Freeport with Fire Pit, Kayaks, & Water Views

Private Waterfront Estate in Freeport with Fire Pit, Kayaks, & Water Views
Freeport
10.0 out of 10, Exceptional, (30 reviews)
"Lovely place and beautiful views! "
United Kingdom
Jacque C.
The price is AU$6,211
includes taxes & fees
15 Aug - 16 Aug
Private Waterfront Estate in Freeport with Fire Pit, Kayaks, & Water Views

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is AU$567
includes taxes & fees
29 July - 30 July
Fortland Island Campground

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
Willard Square Family Home

Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (66 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is AU$1,054
includes taxes & fees
25 Aug - 26 Aug
Arlie`s Digs! - One Block To Willard Beach!

Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
Modern cabin w/ full bath & kitchenette - 03

Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (104 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is AU$656
includes taxes & fees
2 Aug - 3 Aug
Ocean View East End Studio in a Historic Victorian

Portland’s Best Ocean Views from a 40-Foot Private Deck

Portland’s Best Ocean Views from a 40-Foot Private Deck
Munjoy Hill
9.6 out of 10, Exceptional, (27 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
The price is AU$1,184
includes taxes & fees
27 July - 28 July
Portland’s Best Ocean Views from a 40-Foot Private Deck

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (30 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is AU$541
includes taxes & fees
30 July - 31 July
Sunny Spot with Private Parking.

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Jennifer’s VRBO is exactly as cute, clean and cozy as the listing’s photos depict. It is so well maintained that she has living house plants that are thriving 10/10. I can’t wait to stay again!"
United States
Liz P.
The price is AU$623
includes taxes & fees
3 Aug - 4 Aug
Peaceful & minutes from the Old Port with private parking

Island View House BnB Self Check-In # 4 / Free Off-Street Parking

Island View House BnB Self Check-In # 4 / Free Off-Street Parking
Munjoy Hill
9.8 out of 10, Exceptional, (15 reviews)
"Great space in a nice neighborhood location. "
United States
Sheila G.
The price is AU$696
includes taxes & fees
24 Aug - 25 Aug
Island View House BnB Self Check-In # 4 / Free Off-Street Parking

Fall In Love With Portland!

Fall In Love With Portland!
Munjoy Hill
9.4 out of 10, Exceptional, (143 reviews)
"Host was great as well as the accommodations. The place was very clean ."
United States
Lisa B.
The price is AU$1,403
includes taxes & fees
1 Aug - 2 Aug
Fall In Love With Portland!

Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers

Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Munjoy Hill
10.0 out of 10, Exceptional, (53 reviews)
"We have stayed here multiple times and every time it’s amazing!"
United States
Erica L.
The price is AU$1,298
includes taxes & fees
27 July - 28 July
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Great Diamond Island Hotel Reviews

Find out more about Great Diamond Island

Everything you need to know about Great Diamond Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Great Diamond Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Diamond Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Great Diamond Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Diamond Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Great Diamond Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Great Diamond Island holiday rentals we have selected for you start as low as AU$264 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Great Diamond Island rentals

At Expedia, we put the best Great Diamond Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Great Diamond Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Diamond Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Diamond Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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