Book Holiday Homes in Great Diamond Island

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Featured Holiday Homes in Great Diamond Island

The Moonglow! A beautiful ocean view house in Biddeford!

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford ME
When you stay at this vacation home in Biddeford, you'll be near the beach, within a 5-minute drive of Fortunes Rock Beach and Saint Brendan's Chapel.
Opens in a new windowThe Moonglow! A beautiful ocean view house in Biddeford!
Sunny Modern Oasis in Portland’s Trendy East End

Sunny Modern Oasis in Portland’s Trendy East End

Portland ME
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.
Opens in a new windowSunny Modern Oasis in Portland’s Trendy East End
Fantastic Waterfront Views

Fantastic Waterfront Views

Phippsburg ME
The price is AU$381 per night from 11 Mar to 12 Mar
AU$381
11 Mar - 12 Mar
includes taxes & fees
With a stay at this vacation home in Phippsburg (West Point), you'll be within a 15-minute drive of Casco Bay and Popham Beach State Park.
Opens in a new windowFantastic Waterfront Views
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Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Old Orchard Beach ME
The price is AU$1,776 per night from 22 Feb to 23 Feb
AU$1,776
22 Feb - 23 Feb
includes taxes & fees
With a stay at this vacation home in Old Orchard Beach, you'll be by the sea, steps from Old Orchard Beach and a 2-minute drive from Old Orchard Beach Pier.
Opens in a new windowPerfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!
Large, light filled 4 bedroom house - walk to ocean and ferry

Large, light filled 4 bedroom house - walk to ocean and ferry

Peaks Island ME
With a stay at this vacation home in Peaks Island, you'll be by the ocean, just a 1-minute walk from Casco Bay and 6 minutes by foot from Richard Boyd Art ...
Opens in a new windowLarge, light filled 4 bedroom house - walk to ocean and ferry
The Perfect Beach Escape: Cozy 4-Bedroom Retreat

The Perfect Beach Escape: Cozy 4-Bedroom Retreat

Old Orchard Beach ME
With a stay at this vacation home in Old Orchard Beach, you'll be on the beach, a 3-minute walk from Old Orchard Beach and a 2-minute drive from Old Orchard ...
Opens in a new windowThe Perfect Beach Escape: Cozy 4-Bedroom Retreat
Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub

Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub

Old Orchard Beach ME
A stay at this vacation home places you in the heart of Old Orchard Beach, within a 15-minute walk of Old Orchard Beach Pier and Old Orchard Beach.
Opens in a new windowBright & breezy beach house w/ private backyard, central AC, & relaxing hot tub
The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach

Old Orchard Beach ME
The price is AU$749 per night from 16 Feb to 17 Feb
AU$749
16 Feb - 17 Feb
includes taxes & fees
With a stay at this vacation home in Old Orchard Beach, you'll be within a 5-minute drive of Old Orchard Beach Pier and Old Orchard Beach.
Opens in a new windowThe Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach
Beautiful house on the Harpswell Peninsula over looking Casco Bay

Beautiful house on the Harpswell Peninsula over looking Casco Bay

Harpswell ME
With a stay at this vacation home in Harpswell, you'll be by the ocean, just steps from Casco Bay and a 4-minute drive from Mitchell Field.
Opens in a new windowBeautiful house on the Harpswell Peninsula over looking Casco Bay
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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
559 Holiday Homes
Lowest Price
AU$121
Highest Price
AU$1,776
Popular accommodation
The Moonglow! A beautiful ocean view house in Biddeford!, Sunny Modern Oasis in Portland’s Trendy East End, Fantastic Waterfront Views, Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!, Large, light filled 4 bedroom house - walk to ocean and ferry, The Perfect Beach Escape: Cozy 4-Bedroom Retreat, Bright & breezy beach house w/ private backyard, central AC, & relaxing hot tub, The Eagle's Nest ♦ Rooftop Deck ♦ Close to Beach, Beautiful house on the Harpswell Peninsula over looking Casco Bay

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$153 per night from 26 Feb to 27 Feb
AU$153
26 Feb - 27 Feb
includes taxes & fees
With a stay at The Westin Portland Harborview, you'll be centrally located in Portland, steps from State Theatre and Portland Museum of Art.
Opens in a new windowThe Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is AU$121 per night from 19 Feb to 20 Feb
AU$121
19 Feb - 20 Feb
includes taxes & fees
With a stay at Clarion Hotel Portland Airport ME in Portland, you'll be near the airport, within a 15-minute walk of Thompson's Point and Portland Exposition ...
Opens in a new windowClarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
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.
Opens in a new windowPortland Harbor Hotel
Save an average of 15% on thousands of hotels when you're signed in
Old Orchard Beach Inn

Old Orchard Beach Inn

2.5 out of 5
6 Portland Ave Old Orchard Beach ME
Fully refundableReserve now, pay when you stay
When you stay at Old Orchard Beach Inn in Old Orchard Beach, you'll be by the ocean, within a 10-minute walk of Old Orchard Beach Pier and Old Orchard ...
Opens in a new windowOld Orchard Beach Inn
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.