Photo by Robbie Martin

Great Diamond Island Vacation Rentals

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Vacation Rentals in Great Diamond Island

Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (95)
"This beach home was clean and beautiful, it had everything we needed and was in a great location. We loved that it was right on the ocean, which meant amazing sun rises and easy access to walks on the beach. We were there in October, so there wasn’t much going on in Old Orchard beach, but that was okay with us! It was a quiet cozy town when we were there. There were plenty of other places to visit in the surrounding area!"
Gorgeous ocean-front home with stunning beach views
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (89)
"We really enjoyed our stay. This little third floor walk up was a perfect place for my husband and I to explore Portland. It is homey and comfortable and spotless. If you have any issues with mobility you should look elsewhere, but that is disclosed in the listing. The last set of stairs are very steep, but we found it charming. I highly recommend this rental. Well done! "
The price is CA $154
CA $288 total
includes taxes & fees
Nov 6 - Nov 7
Adorable Portland getaway on the Eastern Promenade
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
10.0 out of 10, Exceptional, (34)
"Great place. Cool spot. Host was wonderful. Rooftop was awesome. Highly recommend!"
Artsy Apt/Private Rooftop Deck!/Old Port Arts Dist
Cozy, Elegant and Bright 2 bed in the East End
9.6 out of 10, Exceptional, (35)
"Fabulous location for us as it’s just 1/2 block from our son’s apartment. So close to Casco Bay and the Portland Port area. Walkable to restaurants and shopping. Nice sunny apartment! "
The price is CA $278
CA $511 total
includes taxes & fees
Nov 7 - Nov 8
Cozy, Elegant and Bright 2 bed in the East End
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (194)
"The sunrises, which we could easily view from the balcony, were spectacular! Music and food from the Swick was also good. The location was great for exploring other areas nearby such as Kennebunkport to Portland. Wendy gave excellent details and gave immediate feedback when needed. "
The price is CA $243
CA $477 total
includes taxes & fees
Nov 6 - Nov 7
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (120)
"Great central location for day trips, and then you get relaxing views and sounds of the ocean. There is music from the bar below, but it was a fun atmosphere and we found it enjoyable. "
The price is CA $222
CA $442 total
includes taxes & fees
Nov 6 - Nov 7
Oceanfront Condo! Spectacular Views From Private Large Balcony
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (110)
"We loved the location of this property. It was far enough away from the hustle and bustle to truly relax and enjoy the ocean sounds and sunrises, but close enough that we could easily hop on over to shopping and restaurants. The property was well-maintained, we loved the deck, and being able to walk right out on the beach. Highly recommend!"
Charming 110-year former Inn 10' from the Ocean!
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (139)
"Nice and spacious 2 bedroom unit steps from the promenade. Jennifer was very helpful and accommodating. Easy check in and plenty of parking. Amazing central location. "
The price is CA $232
CA $429 total
includes taxes & fees
Nov 6 - Nov 7
Glorious getaway on Portland's Eastern Promenade.
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.
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
9.8 out of 10, Exceptional, (115)
"Very relaxing getaway."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Beachfront cottage on Fortunes Rocks Beach
10.0 out of 10, Exceptional, (85)
"For anyone who has dreamed of waking up to the sounds of the ocean while watching a spectacular sunrise - this is the place! The house is immaculate and has everything you’ll need! Tyler is awesome and responds to inquiries immediately! We can’t wait to return! "
Beachfront cottage on Fortunes Rocks Beach
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 CA $261
CA $758 total
includes taxes & fees
Nov 19 - Nov 20
Beach House ∆ Prime Location ∆ Steps to the Ocean
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.2 out of 10, Wonderful, (25)
"We had a wonderful visit to OOB to finish off our summer. The cottage is a quick walk to the beach and pier. It was very clean and comfortable for the four of us to relax and recharge in between swimming, playing mini-gold, and enjoying the amusement park."
The price is CA $167
CA $338 total
includes taxes & fees
Dec 3 - Dec 4
Large 2BD cottage 10 min to Pier & Beach Pets ok
Little Miss Cottages
2.5 star property
8.4 out of 10, Very good, (82)
"We stayed because they accept pets. Good place the 24/7 laundry was useable but not everything working"
Little Miss Cottages
100 feet from the ocean 3 bedroom cottage 420 friendly
8.6 out of 10, Excellent, (16)
"Owner should get new cleaners. House smelled like dog urine. Bathroom smelled like human urine. Had to clean floors and bathroom…lots of dirt…not sure the last time floors were I’m mopped. Dog hair on sheets. Beds were not comfortable so be prepared. Parking is a challenge. One paid parking spot in front ($36/day). Can park super close to house for 2nd spot. Owner not very responsive. Had to constantly message for arrival info and didn’t get it until 10 mins after checkin time. No instructions...
100 feet from the ocean 3 bedroom cottage 420 friendly
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
8.2 out of 10, Very good, (12)
"We enjoyed our brief stay"
Dog-friendly cottage with deck & porch - walk to the beach, pier & town
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
10.0 out of 10, Exceptional, (6)
"We had a wonderful stay - myself, my husband and my 6,4, and 2 year old children all enjoyed our time at the beach. We could have done without the harassment of the old lady from cottage 4 (owner perhaps?) telling us to get out at 10am. We were packing the car at 10:02 and trying to get the kids in - we were not in the cottage anymore everything was out. We left the property 10:11am. Her nagging and threats of charging extra were completely unnecessary. It was too bad to have to leave on...
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
8.2 out of 10, Very good, (39)
"Enjoyed our visit. Thanks"
Amazing beachside condo w/private balcony/free WiFi/full kitchen - near Portland
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, (2340)
"Room maintenance needs some attention. Caulk, glue, paint sloppy"
The price is CA $110
CA $120 total
includes taxes & fees
Nov 19 - Nov 20
Casco Bay Hotel, Ascend Hotel Collection
The Westin Portland Harborview
4.0 star property
8.8 out of 10, Excellent, (1003)
"There was nothing about the property i did not like. The bar on the 15th floor was beautiful!"
The price is CA $124
CA $139 total
includes taxes & fees
Dec 1 - Dec 2
The Westin Portland Harborview
Portland Harbor Hotel
4.0 star property
9.2 out of 10, Wonderful, (1374)
"Great place to stay! Comfortable accommodations were excellent and the pantry stations were nice to have."
The price is CA $185
CA $257 total
includes taxes & fees
Dec 1 - Dec 2
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.