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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 ¥16,476
¥34,003 total
includes taxes & fees
Feb 10 - Feb 11
Escape to Positive Outlook

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (15 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is ¥17,299
¥39,506 total
includes taxes & fees
Feb 7 - Feb 8
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 ¥28,244
¥53,020 total
includes taxes & fees
Feb 9 - Feb 10
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 ¥17,103
¥55,916 total
includes taxes & fees
Feb 19 - Feb 20
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

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 ¥31,382
¥60,048 total
includes taxes & fees
Feb 6 - Feb 7
Modern Getaway by the Sea

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)
"Great host communication, arrival and access were easy, house was very clean and comfortable. Will definitely stay again and recommend to fellow Bowdoin families. House is in a great family neighborhood- enjoyed seeing how creative neighbors were with Halloween- would be a great place for kids! Close to town, Bowdoin and so much midcoast has to offer and explore! Thank you!"
United States
Alison O.
The price is ¥19,614
¥57,980 total
includes taxes & fees
Feb 8 - Feb 9
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

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 ¥29,342
¥57,809 total
includes taxes & fees
Feb 11 - Feb 12
Modern & Sunny House Steps from the Promenade. Private Parking!

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 ¥40,012
¥84,915 total
includes taxes & fees
Feb 6 - Feb 7
Willard Square Family Home

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, (56 reviews)
"House was very nice, plenty of room, and accommodating."
United States
Joey S.
The price is ¥22,242
¥76,067 total
includes taxes & fees
Feb 16 - Feb 17
Beach House ∆ Prime Location ∆ Steps to the Ocean

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 ¥44,412
¥67,978 total
includes taxes & fees
Mar 8 - Mar 9
Modern Cottage with Peeks of Ocean Views

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 ¥22,077
¥47,495 total
includes taxes & fees
Feb 8 - Feb 9
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Modern Lakeview Escape | 3BR/2BA

Modern Lakeview Escape | 3BR/2BA
Windham
The price is ¥28,087
¥111,171 total
includes taxes & fees
Feb 6 - Feb 7
Modern Lakeview Escape | 3BR/2BA

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is ¥27,459
¥43,442 total
includes taxes & fees
Feb 8 - Feb 9
Charming 1-bedroom ADU in wonderful Portland neighborhood

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
Old Orchard Beach
9.4 out of 10, Exceptional, (14 reviews)
"Awesome place lots of room very much enjoyed "
United States
Anthony M.
The price is ¥25,043
¥79,974 total
includes taxes & fees
Feb 9 - Feb 10
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Spacious 5BR Family Dream with Private Beach Access

Spacious 5BR Family Dream with Private Beach Access
Old Orchard Beach
10.0 out of 10, Exceptional, (3 reviews)
"Had a great stay. Plenty of amenities that made it nice since it's the winter months. "
United States
Bradford P.
The price is ¥26,196
¥81,061 total
includes taxes & fees
Feb 8 - Feb 9
Spacious 5BR Family Dream with Private Beach Access

The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
8.8 out of 10, Excellent, (3 reviews)
"Great location"
United States
Mark J.
The price is ¥20,844
¥60,006 total
includes taxes & fees
Feb 9 - Feb 10
The 87th Townhome - Local Landmark

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 ¥48,642
¥119,209 total
includes taxes & fees
Mar 5 - Mar 6
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

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 ¥74,360
¥148,127 total
includes taxes & fees
Feb 18 - Feb 19
NEW! Gray Woodland Escape | Golf, Pool & Cinema

On Par for the Beach

On Par for the Beach
Old Orchard Beach
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful, clean property for us and our married kids in their 30's and toddler granddaughters. Fun to use the golf club across the street for easy dinners out. "
United States
Lisa K.
The price is ¥58,512
¥224,967 total
includes taxes & fees
Feb 28 - Mar 1
On Par for the Beach

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (66 reviews)
"Perfect for our girls trip! Right outside portland with gorgeous views; Meghan was so very accommodating as well!"
United States
Allysa Z.
The price is ¥109,445
¥165,645 total
includes taxes & fees
Feb 10 - Feb 11
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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
350
Accommodation
559 Vacation Homes
Lowest Price
¥39,506
Highest Price
¥224,967

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