Photo by Robbie Martin

Holiday Rentals in Great Diamond Island

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Holiday Rentals in Great Diamond Island

Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (88)
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Gorgeous ocean-front home with stunning beach views
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (119)
"This has been our fifth year staying in this condo and we are always super happy with the accommodations! Very clean and well taken care of, it’s an incredible spot.. live music you can listen to from the balcony and beautiful views, also so close to everything!"
The price is €361
includes taxes & fees
2 Oct - 3 Oct
Oceanfront Condo! Spectacular Views From Private Large Balcony
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (53)
"Cute little spot near oxbow. Short drive to downtown. Great kitchen if you cook. Neighborhood seems Soso during the day and strangely decent at night. Pretty ideal. Best deal the weekend we stayed even over all the hotels. Worked out great. "
The price is €388
includes taxes & fees
29 Sept - 30 Sept
Elegant condo - walk to Portland's best restaurants & Old Port
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (80)
"The apartment felt like home from the moment we arrived. The location was fantastic, everything we wanted to do was about 5 minutes away. The stairs up to the 3rd floor are narrow, but structurally sound. We had a great time and would recommend this location to anyone wanting to visit Portland Maine!"
The price is €266
includes taxes & fees
30 Sept - 1 Oct
Adorable Portland getaway on the Eastern Promenade
Walk to Old Port ♦ West End Condo ♦ Parking
9.8 out of 10, Exceptional, (71)
"For the money we were happy with the Accommodations. The host was very helpful, a lot of towels were provided which was nice. Easy access and parking, quiet neighborhood."
The price is €332
includes taxes & fees
29 Oct - 30 Oct
Walk to Old Port ♦ West End Condo ♦ Parking
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (108)
"We really enjoyed our two weeks stay on Willard Beach. It was wonderful to fall asleep and to awaken to the sound of the ocean. John's place is very special. The beds and the couches and the porch seating are all very comfortable. The shower is wonderful. "
Charming 110-year former Inn 10' from the Ocean!
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.2 out of 10, Wonderful, (29)
"Had a great stay! "
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
7.4 out of 10, Good, (26)
"The location was amazing! Walking distance to the pier, and right by the beach! We enjoyed that it was far enough down from the pier that the beach was a bit less crowded but we were still able to walk downtown. The accommodations are very cute and rustic. Some things could use attention, like paint touch ups and the patio table needs replacing… however these were minor issues and we will be back! "
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (31)
"Amazing apartment in perfect location. We parked our car at check in and never took it out until we left. The property manager was extremely receptive and helpful. "
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
NEW TO THE MARKET - 1 block from the beach!
10.0 out of 10, Exceptional, (14)
"Loved the condo. Small but perfect for two people. It was very clean, bed comfortable, the hosts responded within minutes to answer questions. Wouldn’t hesitate at all to stay again. "
The price is €286
includes taxes & fees
6 Oct - 7 Oct
NEW TO THE MARKET - 1 block from the beach!
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
9.8 out of 10, Exceptional, (94)
"Super location. So close and easy to get to many places. Plenty of space for everyone to spread out a little. Paying for driveway parking was so worth it especially when coming home after a long day of sight seeing. Nick is so responsive to all inquiries. All around great stay. "
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (185)
"We wanted a quiet get-a-way after raising 5 children. This was perfect, quiet after Labor Day, beautiful weather, sunrises, and week of the full moon. No obstruction for the sunrises other that a couple days of fog, same with the full moon rises. Unit was clean, nicely furnished with furniture and kitchen items. "
The price is €316
includes taxes & fees
16 Oct - 17 Oct
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
East Grand Ave Fabulous Cottage
9.2 out of 10, Wonderful, (128)
"Close to everything "
East Grand Ave Fabulous Cottage
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
8.2 out of 10, Very good, (36)
"Enjoyed our visit. Thanks"
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
Rent a room in the gorgeous Holt House
8.2 out of 10, Very good, (22)
"We loved staying at the Holt House. It's a truly beautiful building. It's like staying in a hotel from another era. The room was beautifully decorated with victorian decor and we loved it. It was also handy to have access to a full kitchen on the first floor where we washed some of our dishes. Overall, it was a cozy and quiet place to stay."
Rent a room in the gorgeous Holt House
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (136)
"Cute house, apartment is the whole first floor. We enjoyed our stay, near downtown and the eastern promenade. Would recommend."
The price is €407
includes taxes & fees
29 Oct - 30 Oct
Glorious getaway on Portland's Eastern Promenade.
Beachfront cottage on Fortunes Rocks Beach
10.0 out of 10, Exceptional, (81)
"I’ve stayed at this property multiple times over the years with my family in the summertime but this was my first solo trip in the winter. It was the perfect place to relax and recharge with my dog. They had everything I needed and even had the coziest fireplace. I’ll be back next year!"
Beachfront cottage on Fortunes Rocks Beach
Full sized home
9.6 out of 10, Exceptional, (19)
"We only stayed a night but everything was thoughtfully provided-very comfortable beds, week equipped kitchen and great information about places to eat and order food. Thank you for sharing this home!"
The price is €373
includes taxes & fees
1 Oct - 2 Oct
Full sized home
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
9.6 out of 10, Exceptional, (31)
"Thoroughly enjoyed this house.Home had a Great layout . Clean . Beds comfortable . Would stay here again!"
Lowell's Getaway. Kayaking, beaches, dining and AC from this water view home.
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (37)
"Very comfortable. Convenient very easy beach access."
The price is €590
includes taxes & fees
16 Oct - 17 Oct
Beach House ∆ Prime Location ∆ Steps to the Ocean
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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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Other types of properties in Great Diamond Island you may be interested in

Casco Bay Hotel, Ascend Hotel Collection
3.5 star property
8.4 out of 10, Very good, (2150)
"It’s fine but inconvenient without a car. Nothing is within walking distance, especially at night."
The price is €77
includes taxes & fees
20 Oct - 21 Oct
Casco Bay Hotel, Ascend Hotel Collection
Ramada Plaza by Wyndham Portland
3.0 star property
7.6 out of 10, Good, (1022)
"Enjoyed my stay here. Staff is very helpful and friendly. The location is very convenient. "
The price is €98
includes taxes & fees
27 Oct - 28 Oct
Ramada Plaza by Wyndham Portland
Portland Harbor Hotel
4.0 star property
9.2 out of 10, Wonderful, (1352)
"First time stay at this hotel. Look forward to returning again."
The price is €258
includes taxes & fees
27 Oct - 28 Oct
Portland Harbor Hotel
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.