A calm sea with a sailboat and rocky coastline.

Great Diamond Island Vacation Rentals

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Our top choices for Great Diamond Island vacation rentals

1. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is CA $479
CA $523 total
includes taxes & fees
Aug 23 - Aug 24
Fortland Island Campground

2. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (108 reviews)
"Really nice room and location"
United States
Victoria
The price is CA $427
CA $570 total
includes taxes & fees
Sep 1 - Sep 2
The Weldon Hotel

3. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (9 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is CA $745
CA $1,021 total
includes taxes & fees
Aug 31 - Sep 1
Evalina Hotel

4. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (108 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is CA $418
CA $643 total
includes taxes & fees
Aug 23 - Aug 24
Ocean View East End Studio in a Historic Victorian

5. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is CA $329
CA $541 total
includes taxes & fees
Aug 10 - Aug 11
Peaceful & minutes from the Old Port with private parking

6. Vintage Maine & Modern Convenience in Portlands Exclusive East End

Vintage Maine & Modern Convenience in Portlands Exclusive East End
Munjoy Hill
9.8 out of 10, Exceptional, (55 reviews)
"Great location. Short walk to Old Port and shops restaurants. Host was great"
United States
Jeff P.
The price is CA $487
CA $764 total
includes taxes & fees
Aug 13 - Aug 14
Vintage Maine & Modern Convenience in Portlands Exclusive East End

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

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (23 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is CA $272
CA $438 total
includes taxes & fees
Aug 31 - Sep 1
Charming Studio apartment with WiFi, AC in welcoming Portland

8. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (139 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is CA $275
CA $433 total
includes taxes & fees
Sep 6 - Sep 7
Adorable Portland getaway on the Eastern Promenade

9. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (182 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is CA $414
CA $649 total
includes taxes & fees
Sep 1 - Sep 2
Glorious getaway on Portland's Eastern Promenade.

10. Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood

Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood
Munjoy Hill
10.0 out of 10, Exceptional, (19 reviews)
"Great host and very clean, comfortable stay! We all wished we would have had more time here and loved every bit of our stay. Sunrise on the rooftop deck, city lights up there at night. It was wonderful! We hope to return someday! "
United States
JESSICA S.
The price is CA $442
CA $739 total
includes taxes & fees
Sep 7 - Sep 8
Spectacular Views & Comforts of Home in Portland s Most Desirable Neighborhood

11. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (7 reviews)
"Great location within walking distance to activities, food, the bay, etc. "
United States
Anne D.
The price is CA $417
CA $763 total
includes taxes & fees
Aug 10 - Aug 11
NEW 1 BDR-Heart of Munjoy Hill

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

Portland’s Best Ocean Views from a 40-Foot Private Deck
Munjoy Hill
9.4 out of 10, Exceptional, (30 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
The price is CA $732
CA $1,085 total
includes taxes & fees
Sep 1 - Sep 2
Portland’s Best Ocean Views from a 40-Foot Private Deck

13. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is CA $418
CA $842 total
includes taxes & fees
Aug 23 - Aug 24
Willard Square Family Home

14. Eastbayside/Munjoy - Charming Downtown Escape

Eastbayside/Munjoy - Charming Downtown Escape
East Bayside
9.8 out of 10, Exceptional, (37 reviews)
"Very nice location, clean and comfortable!"
United States
Ryan R.
The price is CA $746
CA $1,251 total
includes taxes & fees
Aug 14 - Aug 15
Eastbayside/Munjoy - Charming Downtown Escape

15. Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (42 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 CA $499
CA $805 total
includes taxes & fees
Sep 1 - Sep 2
Modern & Sunny House Steps from the Promenade. Private Parking!

16. 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 CA $458
CA $1,048 total
includes taxes & fees
Aug 16 - Aug 17
Prime Old Port 3BR • Free Parking • Sleeps 8

17. Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (12 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 CA $934
CA $1,389 total
includes taxes & fees
Aug 31 - Sep 1
Harborview - Curated East End Escape w/ Parking

18. 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, (16 reviews)
"Ani was very friendly and communicative and the place was comfortable and inviting. We had a great stay!"
United States
Cristina Q.
The price is CA $658
CA $1,062 total
includes taxes & fees
Sep 2 - Sep 3
4br2ba House parking A Peaceful Oasis on Munjoy Hill

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

Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers
Munjoy Hill
10.0 out of 10, Exceptional, (53 reviews)
"We have stayed here multiple times and every time it’s amazing!"
United States
Erica L.
The price is CA $758
CA $1,221 total
includes taxes & fees
Sep 1 - Sep 2
Hip & Luxurious Garden Retreat for Families, Foodies & Adventurers

20. Newly Renovated 2nd Floor Apt near USM

Newly Renovated 2nd Floor Apt near USM
Oakdale
10.0 out of 10, Exceptional, (17 reviews)
"Per the title great location, cleanliness as advertised."
United States
Edub
The price is CA $696
CA $953 total
includes taxes & fees
Aug 13 - Aug 14
Newly Renovated 2nd Floor Apt near USM
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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