A calm sea with a sailboat and rocky coastline.

Great Diamond Island Holiday Rentals

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Our top choices for Great Diamond Island holiday rentals

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (117 reviews)
"Really nice room and location"
United States
Victoria
The price is AU$680
includes taxes & fees
21 Sept - 22 Sept
The Weldon Hotel

2. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is AU$1,068
includes taxes & fees
13 Sept - 14 Sept
Evalina Hotel

3. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
10.0 out of 10, Exceptional, (111 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
The price is AU$634
includes taxes & fees
14 Sept - 15 Sept
Ocean View East End Studio in a Historic Victorian

4. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (183 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is AU$637
includes taxes & fees
16 Sept - 17 Sept
Glorious getaway on Portland's Eastern Promenade.

5. Prime Old Port 3BR • Free Parking • Sleeps 8

Prime Old Port 3BR • Free Parking • Sleeps 8
Downtown Portland
9.8 out of 10, Exceptional, (164 reviews)
"Everything was great! Excellent location, clean and great communication. Thank you!"
United States
Stephanie W.
The price is AU$1,118
includes taxes & fees
15 Sept - 16 Sept
Prime Old Port 3BR • Free Parking • Sleeps 8

6. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is AU$819
includes taxes & fees
22 Sept - 23 Sept
The Globe House on Munjoy Hill - Walk to Breweries

7. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (27 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is AU$412
includes taxes & fees
5 Oct - 6 Oct
Charming Studio apartment with WiFi, AC in welcoming Portland

8. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is AU$1,288
includes taxes & fees
1 Oct - 2 Oct
Arlie`s Digs! - One Block To Willard Beach!

9. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (131 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
The price is AU$570
includes taxes & fees
22 Sept - 23 Sept
City Amenities, Casco Bay Sunrises and Natural Beauty

10. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Overall amazing experience! Property is beautifully maintained. Perfectly located, within walking distance from bakeries, pubs, and restraunts. Host was responsive and helpful."
United States
Jacqui B.
The price is AU$765
includes taxes & fees
5 Oct - 6 Oct
Modern & Sunny House Steps from the Promenade.

11. Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers

Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Munjoy Hill
10.0 out of 10, Exceptional, (55 reviews)
"Everything from booking to checkout was outstanding! Very clean, great location, easy parking and walking to town. The host quickly communicates; highly recommend this place for your stay in Portland!"
United States
Kirsten Z.
The price is AU$1,264
includes taxes & fees
29 Sept - 30 Sept
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers

12. Casco Bay Vista

Casco Bay Vista
East Deering
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay at Mat's place! Convenient location, very cute apartment with a lovely view of the water. Well equipped for a couple's weekend away. We appreciated the sharp knives for cooking and the comfy couch!"
United States
Charlotte B.
The price is AU$559
includes taxes & fees
14 Sept - 15 Sept
Casco Bay Vista

13. Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood
Munjoy Hill
9.8 out of 10, Exceptional, (43 reviews)
"Wonderful spacious condo for our family stay in Portland. Gracious and attentive hosts. Definitely recommend!"
United States
Kerry N.
The price is AU$1,080
includes taxes & fees
27 Sept - 28 Sept
Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

14. Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (13 reviews)
"It was a beautiful property with everything you could need available. There were a lot of little touches that made it really nice! "
United States
Jeannette B.
The price is AU$1,333
includes taxes & fees
15 Sept - 16 Sept
Harborview - Curated East End Escape w/ Parking

15. East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (42 reviews)
"Very comfortable and stocked well. Lacked for nothing and able to walk to most places. Host checked in which was very nice. Enjoyed Portland."
United States
sheila g.
The price is AU$505
includes taxes & fees
14 Sept - 15 Sept
East end. Walk to food, beer and downtown fun.

16. Island View House BnB Self Check-In # 4 / Free Off-Street Parking

Island View House BnB Self Check-In # 4 / Free Off-Street Parking
Munjoy Hill
9.6 out of 10, Exceptional, (17 reviews)
"Loved the place! Very eclectic. Easy walk to downtown. Definitely will be back!"
United States
Cameron H.
The price is AU$803
includes taxes & fees
16 Sept - 17 Sept
Island View House BnB Self Check-In # 4 / Free Off-Street Parking

17. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

4br2ba House parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (18 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
The price is AU$803
includes taxes & fees
6 Oct - 7 Oct
4br2ba House parking A Peaceful Oasis on Munjoy Hill

18. East End Guesthouse

East End Guesthouse
Munjoy Hill
10.0 out of 10, Exceptional, (3 reviews)
"Fabulous stay!! Felt like we were living in a Crate & Barrel catalog. Great location. "
United States
Ashleigh F.
The price is AU$713
includes taxes & fees
7 Oct - 8 Oct
East End Guesthouse

19. Portland’s Best Ocean Views from a 40-Foot Private Deck

Portland’s Best Ocean Views from a 40-Foot Private Deck
Munjoy Hill
9.6 out of 10, Exceptional, (31 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
The price is AU$1,053
includes taxes & fees
22 Sept - 23 Sept
Portland’s Best Ocean Views from a 40-Foot Private Deck

20. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (9 reviews)
"Great location within walking distance to activities, food, the bay, etc. "
United States
Anne D.
The price is AU$571
includes taxes & fees
8 Oct - 9 Oct
NEW 1 BDR-Heart of Munjoy Hill
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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Top Great Diamond Island Hotel Reviews

Find out more about Great Diamond Island

Everything you need to know about Great Diamond Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Great Diamond Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Diamond Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Great Diamond Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Diamond Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Great Diamond Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Great Diamond Island holiday rentals we have selected for you start as low as AU$226 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Great Diamond Island rentals

At Expedia, we put the best Great Diamond Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Great Diamond Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Diamond Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Diamond Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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