Book Holiday Homes in Great Diamond Island

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Featured Holiday Homes in Great Diamond Island

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2 out of 5
Scarborough
With a stay at this vacation home in Scarborough (Grand Beach), you'll be within a 15-minute drive of Engine and Grand Beach.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)

Buxton
When you stay at this vacation home in Buxton, you'll be on the waterfront and 8 minutes by car from Saco River.
Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option)
The Moonglow! A beautiful ocean view house in Biddeford!

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford
With a stay at this vacation home in Biddeford, you'll be near the beach, within a 15-minute drive of Engine and Fortunes Rock Beach.
The Moonglow! A beautiful ocean view house in Biddeford!
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Beach House ∆ Prime Location ∆ Steps to the Ocean

Beach House ∆ Prime Location ∆ Steps to the Ocean

Old Orchard Beach
The price is AU$786 per night from 5 Jan to 6 Jan
AU$786
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at this vacation home in Old Orchard Beach, you'll be on the beach, within a 10-minute drive of Engine and Old Orchard Beach.
Beach House ∆ Prime Location ∆ Steps to the Ocean
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Lakefront House

Lakefront House

Windham
The price is AU$1,251 per night from 20 Jan to 21 Jan
AU$1,251
includes taxes & fees
20 Jan - 21 Jan 2025
Located in Windham, this vacation home is on the waterfront, within a 10-minute drive of Maine Wildlife Park and Mercy Primary Care.
Lakefront House
Amazing riverfront home with private deck, views, private dock, & fireplace

Amazing riverfront home with private deck, views, private dock, & fireplace

West Bath
Located in Bath, this vacation home is by the ocean, within a 15-minute drive of Casco Bay and Maine Maritime Museum.
Amazing riverfront home with private deck, views, private dock, & fireplace
Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Beautiful Combo Home Located in Downtown Portland - Close to the Beach

Portland
With a stay at this vacation home, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Beautiful Combo Home Located in Downtown Portland - Close to the Beach
Lofty cottage

Lofty cottage

Harpswell
Located in Harpswell, this vacation home is by the ocean, a 1-minute drive from Casco Bay and 9 minutes from Paddleworks.
Lofty cottage
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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
464 Holiday Homes
Lowest Price
AU$166
Highest Price
AU$1,251
Popular accommodation
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough, Stille Wasser, Quiet, secluded spot on Saco River with Dock (Boat lift option), The Moonglow! A beautiful ocean view house in Biddeford!, Beach House ∆ Prime Location ∆ Steps to the Ocean, Spacious & Sunny 4 Bedroom Close to Downtown, hot tub, Lakefront House, Amazing riverfront home with private deck, views, private dock, & fireplace, Beautiful Combo Home Located in Downtown Portland - Close to the Beach, Lofty cottage

Top trending hotels in Great Diamond Island

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$176 per night from 7 Jan to 8 Jan
AU$176
includes taxes & fees
7 Jan - 8 Jan 2025
With a stay at The Westin Portland Harborview, you'll be centrally located in Portland, steps from State Theatre and Portland Museum of Art.
The Westin Portland Harborview
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 25 Dec to 26 Dec
AU$166
includes taxes & fees
25 Dec - 26 Dec
With a stay at Ramada Plaza by Wyndham Portland in Portland (Nasons Corner), you'll be within a 10-minute drive of Maine Mall and Happy Wheels Skate Center.
Ramada Plaza by Wyndham Portland
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$258 per night from 25 Dec to 26 Dec
AU$258
includes taxes & fees
25 Dec - 26 Dec
With a stay at Portland Harbor Hotel, you'll be centrally located in Portland, within a 10-minute drive of Maine Mall and Casco Bay.
Portland Harbor Hotel
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Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
9 Center Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is AU$254 per night from 5 Jan to 6 Jan
AU$254
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Canopy by Hilton Portland Waterfront in Portland (Downtown Portland), you'll be within a 10-minute drive of Maine Mall and Casco Bay.
Canopy by Hilton Portland Waterfront
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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.

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^Subject to availability and chosen travel dates.