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. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (12 reviews)
"A perfectly decent place to stay, plenty of restaurants and bars within reasonable walking distance. Neighborhood is a bit rough, as the listing mentioned, but no problems while I was there. Response time on questions to the host could be better."
Canada
Brian
The price is HK$906
HK$1,503 total
includes taxes & fees
5 Aug - 6 Aug
Studio Apartment near downtown Walkable!

2. 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, (38 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is HK$1,095
HK$3,705 total
includes taxes & fees
26 Aug - 27 Aug
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

3. 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, (81 reviews)
"I had a wonderful week at this perfect place. Met my expectations and way more. So walkable all over Portland. I will be back. Thank you so very much."
United States
Margaret H.
The price is HK$1,318
HK$4,023 total
includes taxes & fees
4 Aug - 5 Aug
Elegant condo - walk to Portland's best restaurants & Old Port

4. 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 HK$3,415
HK$3,722 total
includes taxes & fees
23 Aug - 24 Aug
Fortland Island Campground

5. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (106 reviews)
"Really nice room and location"
United States
Victoria
The price is HK$3,084
HK$3,950 total
includes taxes & fees
26 Aug - 27 Aug
The Weldon Hotel

6. 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, (106 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is HK$2,352
HK$3,667 total
includes taxes & fees
26 Aug - 27 Aug
Ocean View East End Studio in a Historic Victorian

7. 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 HK$2,094
HK$3,145 total
includes taxes & fees
4 Aug - 5 Aug
Adorable Portland getaway on the Eastern Promenade

8. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (30 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 HK$2,016
HK$3,146 total
includes taxes & fees
3 Aug - 4 Aug
Sunny Spot with Private Parking.

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."
United States
Rob M.
The price is HK$1,128
HK$3,358 total
includes taxes & fees
11 Aug - 12 Aug
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

10. 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 HK$2,223
HK$3,748 total
includes taxes & fees
3 Aug - 4 Aug
City Amenities, Casco Bay Sunrises and Natural Beauty

11. 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, (54 reviews)
"Great location. Short walk to Old Port and shops restaurants. Host was great"
United States
Jeff P.
The price is HK$3,175
HK$4,768 total
includes taxes & fees
2 Aug - 3 Aug
Vintage Maine & Modern Convenience in Portlands Exclusive East End

12. 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
9.8 out of 10, Exceptional, (15 reviews)
"Great space in a nice neighborhood location. "
United States
Sheila G.
The price is HK$2,353
HK$4,351 total
includes taxes & fees
5 Aug - 6 Aug
Island View House BnB Self Check-In # 4 / Free Off-Street Parking

13. 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)
"Jennifer’s VRBO is exactly as cute, clean and cozy as the listing’s photos depict. It is so well maintained that she has living house plants that are thriving 10/10. I can’t wait to stay again!"
United States
Liz P.
The price is HK$2,180
HK$3,402 total
includes taxes & fees
2 Aug - 3 Aug
Peaceful & minutes from the Old Port with private parking

14. 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 HK$2,344
HK$4,290 total
includes taxes & fees
3 Aug - 4 Aug
NEW 1 BDR-Heart of Munjoy Hill

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, (105 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
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

16. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.2 out of 10, Wonderful, (29 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is HK$1,889
HK$2,863 total
includes taxes & fees
3 Aug - 4 Aug
Beautiful 1st Floor Apartment & Amazing Shower

17. 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
9.6 out of 10, Exceptional, (5 reviews)
"All was great...clean and convenient."
United States
Krista P.
The price is HK$1,780
HK$4,069 total
includes taxes & fees
17 Aug - 18 Aug
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

18. Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking
West End
10.0 out of 10, Exceptional, (53 reviews)
"Great stay. The apartment is cute, clean, and in a perfect location. Parking was easy, and the mattress was very comfortable. Would definitely stay here again."
United States
Victoria M.
The price is HK$2,172
HK$3,274 total
includes taxes & fees
3 Aug - 4 Aug
Charming West End Hideaway. Private Parking

19. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (181 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is HK$3,113
HK$4,658 total
includes taxes & fees
26 Aug - 27 Aug
Glorious getaway on Portland's Eastern Promenade.

20. Luxury Condo Downtown Portland Old Port

Luxury Condo Downtown Portland Old Port
Downtown Portland
9.4 out of 10, Exceptional, (22 reviews)
"Portland is awesome, the house was in a great location, nice neighborhood and really conveniently located to an abundance of restaurants"
United States
Doug T.
The price is HK$2,195
HK$3,666 total
includes taxes & fees
24 Aug - 25 Aug
Luxury Condo Downtown Portland Old Port
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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