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 $372
CA $633 total
includes taxes & fees
Sep 20 - Sep 21
Fortland Island Campground

2. 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 CA $258
CA $424 total
includes taxes & fees
Sep 17 - Sep 18
Charming Studio apartment with WiFi, AC in welcoming Portland

3. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (144 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is CA $274
CA $436 total
includes taxes & fees
Sep 27 - Sep 28
Adorable Portland getaway on the Eastern Promenade

4. Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (83 reviews)
"It was nice if you like being right in town. There is no view and it's a bit noisy."
United States
Nancy S.
Elegant condo - walk to Portland's best restaurants & Old Port

5. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (39 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is CA $194
CA $652 total
includes taxes & fees
Sep 8 - Sep 9
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

6. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (33 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is CA $274
CA $444 total
includes taxes & fees
Sep 10 - Sep 11
Sunny Spot with Private Parking.

7. 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)
"Lovely home in a beautiful location and Dan is a fantastic host. Ask him about his hot sauce!"
United States
Elliott H.
The price is CA $416
CA $645 total
includes taxes & fees
Sep 6 - Sep 7
Ocean View East End Studio in a Historic Victorian

8. 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 CA $319
CA $566 total
includes taxes & fees
Sep 14 - Sep 15
Casco Bay Vista

9. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is CA $128
CA $501 total
includes taxes & fees
Sep 3 - Sep 4
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

10. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (30 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is CA $136
CA $261 total
includes taxes & fees
Sep 3 - Sep 4
Beautiful 1st Floor Apartment & Amazing Shower

11. Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
West End
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay - lovely building and really nicely kept, and it’s a perfect location if you want to walk down to Old Port, about 20 minutes. Would love to come back!"
United States
Cate
The price is CA $250
CA $641 total
includes taxes & fees
Sep 9 - Sep 10
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

12. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (90 reviews)
"Was great for our few days in Portland! Having a designated parking space was great and the location was convenient for everything we wanted to do."
United States
Britney G.
The price is CA $148
CA $524 total
includes taxes & fees
Sep 7 - Sep 8
Walk to Old Port ♦ West End Condo ♦ Parking

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

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (12 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is CA $342
CA $550 total
includes taxes & fees
Sep 7 - Sep 8
Peaceful & minutes from the Old Port with private parking

14. 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 CA $350
CA $569 total
includes taxes & fees
Sep 3 - Sep 4
Glorious getaway on Portland's Eastern Promenade.

15. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (106 reviews)
"Very nice place, clean, good location. On-street parking was available. Second floor kitchen & bath, so not for those with issues with stairs, but fine for us. Would stay again!"
United States
Gary
The price is CA $231
CA $465 total
includes taxes & fees
Sep 30 - Oct 1
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

16. 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, (41 reviews)
"Exactly as described and in one of the loveliest parts of Portland! Communication with owner was smooth and seamless. Perfect place to get to multiple places of interest in this charming city."
United States
Emily W.
The price is CA $353
CA $581 total
includes taxes & fees
Sep 14 - Sep 15
East end. Walk to food, beer and downtown fun.

17. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (115 reviews)
"Really nice room and location"
United States
Victoria
The price is CA $528
CA $680 total
includes taxes & fees
Sep 21 - Sep 22
The Weldon Hotel

18. Historic Home in the West End. Private Parking.

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (62 reviews)
"This spot was perfect. So cute and very well-kept. Easy to get in and navigate."
United States
Anonymous traveller
The price is CA $315
CA $517 total
includes taxes & fees
Sep 7 - Sep 8
Historic Home in the West End. Private Parking.

19. 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 CA $706
CA $977 total
includes taxes & fees
Sep 7 - Sep 8
Evalina Hotel

20. 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 CA $518
CA $934 total
includes taxes & fees
Sep 7 - Sep 8
Arlie`s Digs! - One Block To Willard Beach!
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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