Photo by Robbie Martin

Great Diamond Island Holiday Rentals

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Holiday Rentals in Great Diamond Island

Comfort Duplex, 3 Bedrooms | Private kitchen
2 duplex
3.0 star property
The price is NZ$609
includes taxes & fees
31 May - 1 Jun
2 duplex
On the beach
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (75)
"Great little condo. Right on the beach! Balcony is wonderful, as is the view from the master. Second bedroom is definitely a “kids” room with the two bunk beds. Garage was great for a car, would not fit the height of a truck"
Gorgeous ocean-front home with stunning beach views
Exterior
Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
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Beach nearby
Little Miss Cottages
2.5 star property
8.2 out of 10, Very good, (68)
"Perfect place for a family to stay for a fair price if you want to stay a few nights and tour around the rest of Maine. Beach was wonderful! "
Little Miss Cottages
Property grounds
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (16)
"Excellent apartment in Old Port area of Portland. Bright, clean, updated, comfortable bed and furniture, lots of amenities. Would definitely stay there again!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Beach
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
7.4 out of 10, Good, (25)
"The unit has a really nice view of downtown and the pier. Cool view of the ferris wheel lit up at night. At first glance, the unit is nicely decorated. However, it needs to be refreshed - there are chunks missing out of the walls, things falling apart, ongoing water damage next to the tub. Maintenance from the building came by on the first morning of the stay to check on the kitchen sink because there was a massive leak happening to the unit below. Overall, it seemed as if no one has been...
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
Beach/ocean view
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (175)
"Even with a snow/ice storm, the beach doesn’t disappoint! Beautiful sunrises, sunsets, and waves crashing. The condo was warm and cozy and I was very happy to be able to watch the Bruins on tv. Already planned my next visit!"
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Property grounds
100 feet from the ocean 3 bedroom cottage 420 friendly
9.2 out of 10, Wonderful, (13)
"The property was great and a very convenient location to the beach, shops, and pier. They have everything you could possibly need except food and clothing! Very clean, TVs and ACs in every room. The only challenge as others mentioned is parking. It is a tight fit and if your tires are on the sidewalk you can be ticketed. On our second to last day we were approached by the parking patrol and told this. He was super nice and said he wouldn't ticket us but another may. I said we were leaving the...
100 feet from the ocean 3 bedroom cottage 420 friendly
Exterior
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.4 out of 10, Exceptional, (17)
"The cottage was clean and accurately described. It was perfect for our needs and we are already looking forward to staying there again in the future."
The price is NZ$517
includes taxes & fees
4 Jun - 5 Jun
Large 2BD cottage 10 min to Pier & Beach Pets ok
Aerial view
Everybody's favorite Maine beach location
9.2 out of 10, Wonderful, (12)
"The property was updated and very clean. The pillows were not very good, but the bed was great! The location was not where we anticipated. It was very easy checking in and out."
Everybody's favorite Maine beach location
Beach nearby
2 min walk to the beach. Pet friendly condo
9.2 out of 10, Wonderful, (23)
"Great place to stay"
The price is NZ$425
includes taxes & fees
3 Jun - 4 Jun
2 min walk to the beach. Pet friendly condo
Property grounds
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
8.2 out of 10, Very good, (32)
"I rated this property a 4 and not lower because of its location. It is front-facing to the ocean, and that is always a gem in my book. Sleeping to the sound of the waves is amazing. The property management (Vacasa) was flawless in their communication and the housekeeping staff did a great job cleaning what they were responsible for cleaning. BUT....... this unit is in dire need of some deep cleaning and at a minimum some TLC in painting and in fixing what doesn't work (i.e., windows, toilet...
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
Private kitchen
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, (88)
"We were in Portland for my daughter’s graduation. Had a very nice weekend trying different restaurants and enjoying lobster rolls."
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Fridge, microwave, oven, stovetop
Full sized home
9.4 out of 10, Exceptional, (3)
"Super clean and neat. We loved it. Perfect for the 5 of us. Great surround. Peaceful and quiet."
The price is NZ$558
includes taxes & fees
9 Jun - 10 Jun
Full sized home
Private kitchen
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
The price is NZ$765
includes taxes & fees
3 Jun - 4 Jun
Elegant condo - walk to Portland's best restaurants & Old Port
3 bedrooms, desk, iron/ironing board, travel cot
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (35)
"The cottage was very nice but the write-up was a little misleading. For example ocean views are very limited—mostly see rooftops, half bath was on ground floor, and stairs to main living area."
The price is NZ$1,063
includes taxes & fees
30 May - 31 May
Beach House ∆ Prime Location ∆ Steps to the Ocean
2 bedrooms, cots/infant beds, Internet, bed sheets
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
7.0 out of 10, Good, (6)
"This home was clean, bright and comfortable. Great location, no issues. Would definitely stay here again."
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Beach nearby
NEW TO THE MARKET - 1 block from the beach!
10.0 out of 10, Exceptional, (6)
"It was great. Good location and very clean!"
The price is NZ$525
includes taxes & fees
30 May - 31 May
NEW TO THE MARKET - 1 block from the beach!
Property grounds
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (99)
"Lovely home in a beautiful location. Very welcoming, cozy, and friendly. Easy check-in and check-out process. The owner was very accommodating and helpful. Made amazing memories and look forward to returning soon. Thank you so much!"
Charming 110-year former Inn 10' from the Ocean!
Beach
350 Yards to the beach. Pet friendly!
8.2 out of 10, Very good, (23)
"Clean, easy access to everything! Fantastic stay will come again! Thank you!"
The price is NZ$354
includes taxes & fees
30 May - 31 May
350 Yards to the beach. Pet friendly!
Don't see what you're looking for?
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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.

Other types of properties in Great Diamond Island you may be interested in

Honeymoon Suite, 1 King Bed
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1189)
"Great staff. Very attentive "
The price is NZ$557
includes taxes & fees
9 Jun - 10 Jun
Portland Harbor Hotel
Lobby
Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.6 out of 10, Excellent, (1517)
"Newer, clean facility. Less than 100 yards away from the mall parking lot. Really enjoyed my stay here."
The price is NZ$158
includes taxes & fees
3 Jun - 4 Jun
Casco Bay Hotel, Ascend Hotel Collection
Bar (on property)
Canopy by Hilton Portland Waterfront
4.0 star property
9.4 out of 10, Exceptional, (652)
"Great hotel in a good location along the waterfront. The rooms were lovely, and the rooftop bar is great. "
The price is NZ$506
includes taxes & fees
2 Jun - 3 Jun
Canopy by Hilton Portland Waterfront
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Great Diamond Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Great Diamond Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Great Diamond Island. Seeing all the best attractions is bound to make you fall in love with Great Diamond Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Great Diamond Island short-term rentals, that won’t be hard to do.

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