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Our top choices for Great Diamond Island holiday 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 HK$820
HK$1,675 total
includes taxes & fees
1 Feb - 2 Feb
Escape to Positive Outlook

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 HK$1,405
HK$2,638 total
includes taxes & fees
3 Feb - 4 Feb
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 HK$851
HK$2,756 total
includes taxes & fees
1 Feb - 2 Feb
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

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 HK$1,107
HK$3,784 total
includes taxes & fees
16 Feb - 17 Feb
Beach House ∆ Prime Location ∆ Steps to the Ocean

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 HK$1,093
HK$3,021 total
includes taxes & fees
2 Feb - 3 Feb
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

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 HK$1,561
HK$3,030 total
includes taxes & fees
19 Feb - 20 Feb
Modern Getaway by the Sea

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 HK$1,242
HK$2,572 total
includes taxes & fees
1 Feb - 2 Feb
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 HK$2,071
HK$4,314 total
includes taxes & fees
3 Mar - 4 Mar
Willard Square Family Home

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is HK$1,367
HK$2,189 total
includes taxes & fees
5 Feb - 6 Feb
Charming 1-bedroom ADU in wonderful Portland neighborhood

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 HK$2,225
HK$3,473 total
includes taxes & fees
10 Feb - 11 Feb
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)
"Wasn’t clean. Ran out of TP. Requested more but didn’t get any. So had to buy some. Need curtains on the windows. Would be nice to have something to put the luggage on in the rooms so not having to get things off the floor. With one bathroom it would be nice to have more mirrors to use when getting ready. "
United States
Anonymous traveller
The price is HK$1,098
HK$2,363 total
includes taxes & fees
1 Feb - 2 Feb
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Modern Lakeview Escape | 3BR/2BA

Modern Lakeview Escape | 3BR/2BA
Windham
The price is HK$1,397
HK$5,531 total
includes taxes & fees
1 Feb - 2 Feb
Modern Lakeview Escape | 3BR/2BA

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 HK$1,049
HK$3,696 total
includes taxes & fees
3 Feb - 4 Feb
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (8 reviews)
"We had a fantastic stay. Alexa was a wonderful host!"
United States
Desmond L.
The price is HK$1,899
HK$4,667 total
includes taxes & fees
2 Feb - 3 Feb
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

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 HK$1,303
HK$4,007 total
includes taxes & fees
2 Feb - 3 Feb
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 HK$1,156
HK$3,108 total
includes taxes & fees
1 Feb - 2 Feb
The 87th Townhome - Local Landmark

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.
On Par for the Beach

NEW! Gray Woodland Escape | Golf, Pool & Cinema

NEW! Gray Woodland Escape | Golf, Pool & Cinema
Gray
10.0 out of 10, Exceptional, (1 review)
NEW! Gray Woodland Escape | Golf, Pool & Cinema

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 HK$5,445
HK$8,104 total
includes taxes & fees
1 Feb - 2 Feb
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
358
Accommodation
559 Vacation Homes
Lowest Price
HK$1,948
Highest Price
HK$8,104

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