Photo by Robbie Martin

Holiday Homes in Great Diamond Island

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Our top choices for Great Diamond Island holiday homes

Holiday Home in West Point

Escape to Positive Outlook
10.0 out of 10, Exceptional, (3)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is NZ$326
includes taxes & fees
4 Jan - 5 Jan 2026
Escape to Positive Outlook

Holiday Home in West Point

Fantastic Waterfront Views
9.6 out of 10, Exceptional, (14)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is NZ$508
includes taxes & fees
2 Jan - 3 Jan 2026
Fantastic Waterfront Views

Holiday Home in Old Orchard Beach

3BR Coastal Gem with a 5 Min Drive to Ocean Fun
10.0 out of 10, Exceptional, (6)
"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 NZ$610
includes taxes & fees
4 Jan - 5 Jan 2026
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

Holiday Home in Harpswell

Full sized home
9.8 out of 10, Exceptional, (50)
"It was a very nice house to stay at. "
United States
Anonymous traveller
The price is NZ$627
includes taxes & fees
26 Jan - 27 Jan 2026
Full sized home
9.0 out of 10, Wonderful, (24)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is NZ$689
includes taxes & fees
4 Jan - 5 Jan 2026
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
10.0 out of 10, Exceptional, (55)
"Excellent location for an after Labor Day vacation. Easy access to the beach. Quiet street. Very nice accommodations with plenty of room. "
United States
Charles C.
The price is NZ$786
includes taxes & fees
1 Jan - 2 Jan 2026
Beach House ∆ Prime Location ∆ Steps to the Ocean

Holiday Home in South Portland

Modern Getaway by the Sea
10.0 out of 10, Exceptional, (2)
"Had a nice stay! House was great."
United States
Karen T.
The price is NZ$764
includes taxes & fees
2 Jan - 3 Jan 2026
Modern Getaway by the Sea

Holiday Home in Harpswell

Orchid Harbor, Bailey Island 3BR
9.8 out of 10, Exceptional, (9)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
The price is NZ$808
includes taxes & fees
4 Jan - 5 Jan 2026
Orchid Harbor, Bailey Island 3BR
8.4 out of 10, Very good, (58)
"Quiet, close to everything and east to find."
United States
Jesse M.
The price is NZ$521
includes taxes & fees
3 Jan - 4 Jan 2026
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
10.0 out of 10, Exceptional, (38)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$629
includes taxes & fees
4 Jan - 5 Jan 2026
Modern & Sunny House Steps from the Promenade. Private Parking!

Holiday Home in Brunswick

Maine Luxury Home On the Sea
The price is NZ$1,103
includes taxes & fees
7 Jan - 8 Jan 2026
Maine Luxury Home On the Sea
10.0 out of 10, Exceptional, (1)
"Great property! Spacious and comfortable.Nice location."
United States
rebecca c.
The price is NZ$847
includes taxes & fees
4 Jan - 5 Jan 2026
Spacious 5BR Family Dream with Private Beach Access
8.0 out of 10, Very good, (1)
"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.
The price is NZ$872
includes taxes & fees
5 Jan - 6 Jan 2026
Huge New Townhome 10mins from the Beach

Holiday Home in Windham

Modern Lakeview Escape | 3BR/2BA
2.0 star property
Modern Lakeview Escape | 3BR/2BA
9.4 out of 10, Exceptional, (14)
"Awesome place lots of room very much enjoyed "
United States
Anthony M.
The price is NZ$839
includes taxes & fees
5 Jan - 6 Jan 2026
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
The price is NZ$394
includes taxes & fees
7 Jan - 8 Jan 2026
Charming 1-bedroom ADU in wonderful Portland neighborhood
2.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely fantastic stay! The house is clean, comfortable and has all the amenities to stay in. However with such a great location to all that Portland has to offer taking a quick walk to whatever strikes your fancy is highly recommended. The bakery on the corner has great coffee and baked goods. We didn’t need much from Doug but when I messaged him he was very responsive and accommodating. The beds are extremely comfortably. The location is quiet, within walking distance or a quick uber...
United States
Carl K.
The price is NZ$687
includes taxes & fees
18 Jan - 19 Jan 2026
Chic 3-bedroom house in Munjoy Hill with off-street parking.

Holiday Home in Cape Elizabeth

Modern Cottage with Peeks of Ocean Views
10.0 out of 10, Exceptional, (1)
"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 NZ$755
includes taxes & fees
4 Jan - 5 Jan 2026
Modern Cottage with Peeks of Ocean Views

Holiday Home in Willard Beach

Willard Square Family Home
9.6 out of 10, Exceptional, (9)
"Thoroughly enjoyed this house! "
United States
David W.
The price is NZ$891
includes taxes & fees
1 Jan - 2 Jan 2026
Willard Square Family Home
10.0 out of 10, Exceptional, (2)
"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."
United States
Edwin M.
The price is NZ$1,952
includes taxes & fees
6 Jan - 7 Jan 2026
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury
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 Holiday Homes information

Number of reviews
280
Accommodation
559 Holiday Homes
Lowest Price
NZ$394
Highest Price
NZ$1,952

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