Photo by Robbie Martin

Great Diamond Island Vacation Rentals

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Vacation Rentals in Great Diamond Island

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Fridge, microwave, oven, stovetop

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
Beach House ∆ Prime Location ∆ Steps to the Ocean
3 bedrooms, desk, iron/ironing board, free WiFi

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (38)
"The house is very clean, and it is only a minute walk to the beach. This was the second time we’ve stayed in this house and it won’t be the last! "
The price is CA $213
CA $708 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Beach House ∆ Prime Location ∆ Steps to the Ocean
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (100)
"The view and location are amazing. The house was very comfortable for the three adults on our trip. It’s also very suitable for a family with kids as one of the rooms has two bunk bed sets. It’s comfortable, cozy, and completely relaxing. Within walking distance of the pier and entertainment. Great place to stay. "
Gorgeous ocean-front home with stunning beach views
Charming 110-year former Inn 10' from the Ocean!
Property grounds

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (114)
"This location is EVERYTHING!!! Right on the beach, cozy accommodations with spacious bedrooms was perfect for the 4 of us - with the 3rd bedroom, we could've included another couple! Host John was lovely!!!"
Charming 110-year former Inn 10' from the Ocean!
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Beach nearby, beach towels

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)
Onsite parking

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (119)
"Clean, comfortable and quiet! Beautiful views of ocean."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Interior

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (196)
"My family had a wonderful stay at your condo. They had unbelievably nice weather and got to enjoy your deck and views in early Nov. "
The price is CA $251
CA $493 total
includes taxes & fees
Dec 25 - Dec 26
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Little Miss Cottages
Property grounds

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
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Terrace/patio

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
On the beach

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
Rent a room in the gorgeous Holt House
Exterior

Rent a room in the gorgeous Holt House

8.0 out of 10, Very good, (24)
"This was a perfect place, close to everything in Portland! "
Rent a room in the gorgeous Holt House
1 Bedroom Downtown Condo, Walk to the Beach & Pier
Beach

1 Bedroom Downtown Condo, Walk to the Beach & Pier

9.6 out of 10, Exceptional, (18)
"We loved our stay at the condo. We would definitely stay here again. It was so close to everything we wanted to do and you can walk right down to the beach! "
1 Bedroom Downtown Condo, Walk to the Beach & Pier
Spacious 3BR, 12-Min to OOB Beach & Pier, Sleeps 8
Smart TV

Spacious 3BR, 12-Min to OOB Beach & Pier, Sleeps 8

9.0 out of 10, Wonderful, (2)
"Our stay at the property was great."
Spacious 3BR, 12-Min to OOB Beach & Pier, Sleeps 8
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
1 bedroom, free WiFi, bed sheets

Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC

9.6 out of 10, Exceptional, (26)
"Repeat visit. Short walk to beach. Convenient to stores if you want to shop. Cottage comfortable. We’ll be back!"
Charming Cottage Steps to Pine Point Bch - 1 mile OOB outside Scarborough w/ AC
Glorious getaway on Portland's Eastern Promenade.
Property grounds

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (142)
"We had a wonderful night in Portland! We spent the afternoon shopping in Freeport and arrived at the apartment around 5. Very easy finding parking on the street and no trouble getting inside. The apartment is absolutely adorable! Between the colors and decorations, it just gives off this girly, cozy vibe. There were 4 of us and we all had room to sleep comfortably. Wish we could have stayed another night! "
The price is CA $182
CA $366 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Glorious getaway on Portland's Eastern Promenade.
NEW TO THE MARKET - 1 block from the beach!
Beach nearby

NEW TO THE MARKET - 1 block from the beach!

10.0 out of 10, Exceptional, (18)
"Close walk to beach restaraunts and pier very nice inside"
NEW TO THE MARKET - 1 block from the beach!
Full sized home
Interior

Full sized home

9.6 out of 10, Exceptional, (24)
"The house is very clean, and it's very well situated. There are plenty of room in and out. Will come again."
The price is CA $323
CA $537 total
includes taxes & fees
Dec 25 - Dec 26
Full sized home
Cozy, Elegant and Bright 2 bed in the East End
Fridge, microwave, oven, stovetop

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 $287
CA $527 total
includes taxes & fees
Dec 26 - Dec 27
Cozy, Elegant and Bright 2 bed in the East End
Escape to the Beach! Cozy Condo in downtown OOB.
Beach nearby

Escape to the Beach! Cozy Condo in downtown OOB.

9.6 out of 10, Exceptional, (21)
"Cute little condo within a short walk from everything. Quiet and clean. Would recommend!"
The price is CA $142
CA $310 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Escape to the Beach! Cozy Condo in downtown OOB.
100 feet from the ocean 3 bedroom cottage 420 friendly
Interior

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
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

The Westin Portland Harborview
View from room

The Westin Portland Harborview

4.0 star property
8.8 out of 10, Excellent, (1005)
"I had an incredible stay! This was my first time at the Westin Harborview. Upon check-in I was awarded “Guest of the Day” status with a top floor upgrade. It was such a sweet surprise and a wonderful experience. The harbor view is quite lovely and the next morning I watched a couple of cargo ships move through the draw bridge while sipping delicious in room Starbucks coffee. From check-in to upgrade, which included a complimentary breakfast in C2 (delicious options and friendly warm service), to...
The price is CA $141
CA $158 total
includes taxes & fees
Jan 8 - Jan 9, 2025
The Westin Portland Harborview
Ramada Plaza by Wyndham Portland
Exterior

Ramada Plaza by Wyndham Portland

3.0 star property
7.6 out of 10, Good, (1011)
"This was a great place to stay at. Very easy to locate and close enough to everything. The room was very clean and stocked perfectly. It was a breeze to check in and out. There are 2 hot tubs on site. Definately a great place to stay especially for the money."
The price is CA $134
CA $149 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Ramada Plaza by Wyndham Portland
Portland Harbor Hotel
Honeymoon Suite, 1 King Bed

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1428)
"Nice hotel in a great location!"
The price is CA $165
CA $238 total
includes taxes & fees
Jan 5 - Jan 6, 2025
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.