Book Holiday Homes in Great Diamond Island

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Featured Holiday Homes in Great Diamond Island

Beautiful Oceanfront House- Stunning Water Views

Beautiful Oceanfront House- Stunning Water Views

Harpswell ME
Located in Harpswell, this vacation home is a 1-minute drive from Casco Bay and 7 minutes from Androscoggin River.
Opens in a new windowBeautiful Oceanfront House- Stunning Water Views
Centerview cottage

Centerview cottage

Harpswell ME
The price is AU$662 per night from 16 May to 17 May
AU$662
16 May - 17 May
includes taxes & fees
Located in Harpswell, this vacation home is by the ocean, within a 15-minute drive of Paddleworks and Bailey Island Bridge.
Opens in a new windowCenterview cottage
4-bedroom vacation home steps to Old Orchard Beach Pier

4-bedroom vacation home steps to Old Orchard Beach Pier

Old Orchard Beach ME
With a stay at this vacation home in Old Orchard Beach, you'll be within a 15-minute walk of Old Orchard Beach Pier and Old Orchard Beach.
Opens in a new window4-bedroom vacation home steps to Old Orchard Beach Pier
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5 Star Back Cove Apartment with water view!

5 Star Back Cove Apartment with water view!

Portland ME
With a stay at this vacation home in Portland (Back Cove), you'll be a 4-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Opens in a new window5 Star Back Cove Apartment with water view!
The Lookout by Bayley Vacation Rentals

The Lookout by Bayley Vacation Rentals

Saco ME
With a stay at this vacation home in Saco (Camp Ellis), you'll be a 5-minute drive from Old Orchard Beach and 6 minutes from Old Orchard Beach Pier.
Opens in a new windowThe Lookout by Bayley Vacation Rentals
Rare West End Home • Walk to Old Port, Harbor View

Rare West End Home • Walk to Old Port, Harbor View

Portland ME
The price is AU$964 per night from 21 May to 22 May
AU$964
21 May - 22 May
includes taxes & fees
With a stay at this vacation home in Portland (West End), you'll be a 5-minute drive from Thompson's Point and 8 minutes from Maine Mall.
Opens in a new windowRare West End Home • Walk to Old Port, Harbor View
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Saco ME
With a stay at this vacation home in Saco (Kinney Shores), you'll be within a 5-minute drive of Old Orchard Beach Pier and Old Orchard Beach.
Opens in a new windowGorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!
Charming Nautical Retreat-3 BR +Fully Equipped+ Short walk to beach!

Charming Nautical Retreat-3 BR +Fully Equipped+ Short walk to beach!

Old Orchard Beach ME
When you stay at this vacation home in Old Orchard Beach, you'll be near the beach, within a 10-minute walk of Old Orchard Beach Pier and Old Orchard Beach.
Opens in a new windowCharming Nautical Retreat-3 BR +Fully Equipped+ Short walk to beach!
Sun-Kissed Beach Getaway – Family-Friendly, Close to Beach, Private Yard!

Sun-Kissed Beach Getaway – Family-Friendly, Close to Beach, Private Yard!

Saco ME
With a stay at this vacation home, you'll be centrally located in Saco, a 5-minute drive from Old Orchard Beach and 7 minutes from Old Orchard Beach Pier.
Opens in a new windowSun-Kissed Beach Getaway – Family-Friendly, Close to Beach, Private Yard!
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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.

Great Diamond Island Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Great Diamond Island vacation homes are the perfect way for you to wing it.

Holiday houses in Great Diamond Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Great Diamond Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Great Diamond Island adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Great Diamond Island with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Great Diamond Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Great Diamond Island Holiday Homes essential information

Accommodation
558 Holiday Homes
Lowest Price
AU$209
Highest Price
AU$964
Popular accommodation
Beautiful Oceanfront House- Stunning Water Views, Centerview cottage, 4-bedroom vacation home steps to Old Orchard Beach Pier, 5 Star Back Cove Apartment with water view!, The Lookout by Bayley Vacation Rentals, Rare West End Home • Walk to Old Port, Harbor View, Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!, Charming Nautical Retreat-3 BR +Fully Equipped+ Short walk to beach!, Sun-Kissed Beach Getaway – Family-Friendly, Close to Beach, Private Yard!

Top trending hotels in Great Diamond Island

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$337 per night from 25 May to 26 May
AU$337
25 May - 26 May
includes taxes & fees
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, a 5-minute drive from Thompson's Point and 9 minutes from Maine Mall.
Opens in a new windowPortland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$276 per night from 26 May to 27 May
AU$276
26 May - 27 May
includes taxes & fees
With a stay at Portland Regency Hotel & Spa, you'll be centrally located in Portland, within a 10-minute drive of Thompson's Point and Maine Mall.
Opens in a new windowPortland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is AU$271 per night from 26 May to 27 May
AU$271
26 May - 27 May
includes taxes & fees
Located in Portland (Downtown Portland), Cambria Hotel Portland Downtown-Old Port is within a 10-minute drive of Thompson's Point and Maine Mall.
Opens in a new windowCambria Hotel Portland Downtown-Old Port
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HomeAwhile

HomeAwhile

2 out of 5
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 31 May to 1 June
AU$209
31 May - 1 June
includes taxes & fees
When you stay at HomeAwhile in Scarborough, you'll be near the airport, a 2-minute drive from Maine Mall and 8 minutes from Thompson's Point.
Opens in a new windowHomeAwhile
Don't see what you're looking for?
See all available properties in Great Diamond Island
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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.

Top Picks

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^Subject to availability and chosen travel dates.