A calm sea with a sailboat and rocky coastline.

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Great Diamond Island vacation homes

Interior

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, (61 reviews)
"Nice place. Good location."
United States
Rob M.
The price is AED 640
AED 1,691 total
includes taxes & fees
11 Aug - 12 Aug
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Outdoor dining

The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (100 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is AED 1,480
AED 2,566 total
includes taxes & fees
18 Aug - 19 Aug
The Globe House on Munjoy Hill - Walk to Breweries
Outdoor dining

Spacious Portland Home + Parking

Spacious Portland Home + Parking
Parkside
8.8 out of 10, Excellent, (3 reviews)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
The price is AED 1,010
AED 2,859 total
includes taxes & fees
22 Jul - 23 Jul
Spacious Portland Home + Parking
Outdoor dining

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, (42 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AED 1,561
AED 2,446 total
includes taxes & fees
19 Jul - 20 Jul
Modern & Sunny House Steps from the Promenade. Private Parking!
Terrace/patio

Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (54 reviews)
"Wonderful stay!"
United States
Erika T.
The price is AED 744
AED 1,363 total
includes taxes & fees
21 Jul - 22 Jul
Full sized home
Interior

Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is AED 823
AED 1,702 total
includes taxes & fees
21 Jul - 22 Jul
Tranquility between the Lakes & Sea
Property grounds

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is AED 1,484
AED 2,118 total
includes taxes & fees
19 Jul - 20 Jul
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
TV, offices

Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
10.0 out of 10, Exceptional, (2 reviews)
"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."
United States
Richard G.
Windham Lakefront: Fire Pit and Modern Comforts
Interior

Spacious 4-bedroom house located in the heart of Portland, ME.

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
10.0 out of 10, Exceptional, (14 reviews)
"Great place great location. "
United States
Chris f.
The price is AED 2,736
AED 4,436 total
includes taxes & fees
2 Aug - 3 Aug
Spacious 4-bedroom house located in the heart of Portland, ME.
Exterior

The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
9.6 out of 10, Exceptional, (8 reviews)
"Great location"
United States
Mark J.
The price is AED 1,880
AED 3,447 total
includes taxes & fees
18 Aug - 19 Aug
The 87th Townhome - Local Landmark
Living area

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

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Ligonia
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 AED 1,928
AED 3,771 total
includes taxes & fees
5 Aug - 6 Aug
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Dining

Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
TV

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 AED 675
AED 1,119 total
includes taxes & fees
3 Aug - 4 Aug
Mid Coast Getaway w/ water views
Interior

Niblet Cottage by Bayley Vacation Rentals

Niblet Cottage by Bayley Vacation Rentals
Grand Beach
8.0 out of 10, Very Good, (13 reviews)
"Absolutely wonderful two bedroom pet friendly house. Close to Old Orchard Pier. Bayleys Realtor accessible at anytime if needed. Would definitely return!"
United States
Denise B.
The price is AED 1,050
AED 4,626 total
includes taxes & fees
23 Jul - 24 Jul
Niblet Cottage by Bayley Vacation Rentals
Exterior detail

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, (76 reviews)
"This is such a great house and it was perfect for our group! We would definitely stay there again "
United States
Catherine T.
The price is AED 5,142
AED 6,970 total
includes taxes & fees
7 Aug - 8 Aug
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Property grounds

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 AED 1,084
AED 1,754 total
includes taxes & fees
19 Jul - 20 Jul
Centerview cottage
Beach

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Buxton
6.0 out of 10, (1 review)
"Overall, value property. It's a very old home that was slightly renovated. Pros. 3 bedrooms, washer dryer, good price Cons. Smelled musty, pans not usable for cooking, small living room.Host was great with communication, and the stay was worth the price."
United States
Renee D.
The price is AED 760
AED 1,625 total
includes taxes & fees
21 Jul - 22 Jul
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Smart TV

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.
The price is AED 1,071
AED 2,593 total
includes taxes & fees
16 Aug - 17 Aug
Huge New Townhome 10mins from the Beach
Smart TV

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
9.0 out of 10, Wonderful, (6 reviews)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is AED 826
AED 1,706 total
includes taxes & fees
21 Jul - 22 Jul
Beautiful 3BR Home with Office in Town of Brunswick with King beds
3 bedrooms, desk, iron/ironing board, travel crib

⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!

⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!
Old Orchard Beach
10.0 out of 10, Exceptional, (8 reviews)
"The host was extremely responsive, the house perfectly accommodated our needs, and the beds were super comfortable. Highly recommend!"
United States
Tina B.
The price is AED 1,194
AED 2,230 total
includes taxes & fees
21 Jul - 22 Jul
⚓ Cozy 3BR Coastal Retreat • Private Yard & Fire Pit • 5 Min to Beach!
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

Comfort Inn Saco-Old Orchard Beach

Comfort Inn Saco-Old Orchard Beach

10/10 Excellent
"This looks like a new hotel. It was clean, comfortable beds, large rooms, good bathroom. Breakfast was good. Staff nice and helpful. Location good we just had one night but lots of families there enjoying pool and amenities."
Margaret 1-night trip
Posted less than an hour ago
Comfort Inn Saco-Old Orchard Beach