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Our top choices for Great Diamond Island vacation homes

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3 reviews)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is ¥14,714
¥31,790 total
includes taxes & fees
Jan 27 - Jan 28
Escape to Positive Outlook

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (14 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is ¥16,349
¥38,142 total
includes taxes & fees
Jan 27 - Jan 28
Fantastic Waterfront Views

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (50 reviews)
"Super clean and lovely place to stay! Highly recommend!"
United States
Evan B.
The price is ¥28,026
¥52,611 total
includes taxes & fees
Jan 27 - Jan 28
Full sized home

3BR Coastal Gem with a 5 Min Drive to Ocean Fun

3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Old Orchard Beach
10.0 out of 10, Exceptional, (6 reviews)
"I loved that the hosts live nearby and responded quickly when we needed anything. Having a washer and dryer onsite is great for longer stays. Beds were comfortable and plenty of blankets and pillows. Highly recommend this property."
United States
Terry
The price is ¥16,971
¥55,485 total
includes taxes & fees
Feb 19 - Feb 20
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
9.0 out of 10, Wonderful, (25 reviews)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is ¥21,798
¥60,248 total
includes taxes & fees
Jan 27 - Jan 28
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is ¥19,463
¥52,612 total
includes taxes & fees
Jan 27 - Jan 28
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Modern Getaway by the Sea

Modern Getaway by the Sea
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"Had a nice stay! House was great."
United States
Karen T.
The price is ¥31,140
¥59,076 total
includes taxes & fees
Feb 2 - Feb 3
Modern Getaway by the Sea

Entire ideally located home in Cape Elizabeth’s coveted seaside community

Entire ideally located home in Cape Elizabeth’s coveted seaside community
Cape Elizabeth
10.0 out of 10, Exceptional, (4 reviews)
"The host was welcoming and it was an easy and smooth check in and check out process. Place was a great spot for my friends and I during our stay for a pond hockey tournament."
United States
Kerry W.
The price is ¥26,064
¥60,656 total
includes taxes & fees
Jan 28 - Jan 29
Entire ideally located home in Cape Elizabeth’s coveted seaside community

Huge New Townhome 10mins from the Beach

Huge New Townhome 10mins from the Beach
Saco
8.0 out of 10, Very Good, (1 review)
"The only big issue was that the VRBO listing gave us the wrong address. It sent us to Scarborough instead of Saco. Luckily we were familiar with the area and I knew that Saco was close to Old Orchard Beach, which was mentioned in the listing, so I did a google map search of the same address in Saco and it looked like the pictures. My elderly parents were relieved that we didn’t get scammed. Lol. The place was clean and large and easy to get on the highway. It’s 2 and a half baths, not 3 full...
United States
Stacy H.
Huge New Townhome 10mins from the Beach

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (38 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is ¥24,749
¥51,585 total
includes taxes & fees
Jan 27 - Jan 28
Modern & Sunny House Steps from the Promenade. Private Parking!

Modern Lakeview Escape | 3BR/2BA

Modern Lakeview Escape | 3BR/2BA
Windham
The price is ¥25,379
¥104,543 total
includes taxes & fees
Jan 27 - Jan 28
Modern Lakeview Escape | 3BR/2BA

Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean
Old Orchard Beach
10.0 out of 10, Exceptional, (55 reviews)
"House was very nice, plenty of room, and accommodating."
United States
Joey S.
The price is ¥21,090
¥73,902 total
includes taxes & fees
Jan 27 - Jan 28
Beach House ∆ Prime Location ∆ Steps to the Ocean

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very Good, (58 reviews)
"Quiet, close to everything and east to find."
United States
Jesse M.
The price is ¥21,907
¥47,129 total
includes taxes & fees
Jan 27 - Jan 28
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is ¥21,798
¥35,640 total
includes taxes & fees
Jan 27 - Jan 28
Charming 1-bedroom ADU in wonderful Portland neighborhood

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
South Portland
10.0 out of 10, Exceptional, (1 review)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
The price is ¥31,529
¥97,501 total
includes taxes & fees
Jan 27 - Jan 28
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

Modern Cottage with Peeks of Ocean Views

Modern Cottage with Peeks of Ocean Views
Cape Elizabeth
10.0 out of 10, Exceptional, (1 review)
"Very cute property, perfect location! Had every amenity we could possibly need. The home was decorated so cutely and the shower was AMAZING! I’m coming back just for the shower! "
United States
Christina S.
The price is ¥44,375
¥68,091 total
includes taxes & fees
Jan 27 - Jan 28
Modern Cottage with Peeks of Ocean Views

Willard Square Family Home

Willard Square Family Home
Willard Beach
9.6 out of 10, Exceptional, (9 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is ¥39,704
¥84,261 total
includes taxes & fees
Feb 1 - Feb 2
Willard Square Family Home

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."
United States
Edwin M.
The price is ¥56,052
¥176,502 total
includes taxes & fees
Jan 27 - Jan 28
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home

Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home
3.5 star property
Gray
The price is ¥71,283
¥146,563 total
includes taxes & fees
Feb 5 - Feb 6
Gray Woodland Escape Golf, Pool & Cinema 5 Bedroom Home

NEW! Gray Woodland Escape | Golf, Pool & Cinema

NEW! Gray Woodland Escape | Golf, Pool & Cinema
Gray
10.0 out of 10, Exceptional, (1 review)
The price is ¥73,786
¥146,984 total
includes taxes & fees
Jan 27 - Jan 28
NEW! Gray Woodland Escape | Golf, Pool & Cinema
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

Great Diamond Island Vacation Homes information

Number of reviews
264
Accommodation
559 Vacation Homes
Lowest Price
¥35,640
Highest Price
¥176,502

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