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. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (9 reviews)
"Location and parking were perfect for our first visit to Portland"
United States
Linda
The price is CA $199
CA $442 total
includes taxes & fees
Oct 19 - Oct 20
Willard Beach–Apartment Near Portland & Parks

2. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (155 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is CA $250
CA $408 total
includes taxes & fees
Oct 26 - Oct 27
Adorable Portland getaway on the Eastern Promenade

3. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
The price is CA $177
CA $325 total
includes taxes & fees
Nov 1 - Nov 2
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

4. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (126 reviews)
"Really nice room and location"
United States
Victoria
The price is CA $273
CA $404 total
includes taxes & fees
Nov 2 - Nov 3
The Weldon Hotel

5. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.2 out of 10, Very good, (16 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
The price is CA $126
CA $157 total
includes taxes & fees
Oct 18 - Oct 19
Portland 1-bedroom with enclosed porch & parking

6. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (15 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
The price is CA $417
CA $666 total
includes taxes & fees
Nov 16 - Nov 17
Evalina Hotel

7. 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, (41 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is CA $197
CA $662 total
includes taxes & fees
Oct 18 - Oct 19
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

8. 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, (114 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 CA $424
CA $654 total
includes taxes & fees
Oct 18 - Oct 19
Ocean View East End Studio in a Historic Victorian

9. Willard By the Sea - 30 ft to the beach- 2nd floor

Willard By the Sea - 30 ft to the beach- 2nd floor
Willard
10.0 out of 10, Exceptional, (15 reviews)
"Fantastic beach location and comfortable unit equipped with air conditioning (essential during the heat wave that occurred during our stay). Clean rooms, good size and full kitchen; comfortable furnishings.Only caution is that this is a beach-side location and appears to have a bit of a price premium for that reason. It’s justified but only if you’re planning to make good use of the beach."
United States
Gerald B.
The price is CA $305
CA $779 total
includes taxes & fees
Nov 17 - Nov 18
Willard By the Sea - 30 ft to the beach- 2nd floor

10. East End Guesthouse

East End Guesthouse
Munjoy Hill
10.0 out of 10, Exceptional, (5 reviews)
"Fabulous stay!! Felt like we were living in a Crate & Barrel catalog. Great location. "
United States
Ashleigh F.
The price is CA $352
CA $572 total
includes taxes & fees
Oct 27 - Oct 28
East End Guesthouse

11. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
The price is CA $237
CA $406 total
includes taxes & fees
Oct 18 - Oct 19
Sunny Spot with Private Parking.

12. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.6 out of 10, Excellent, (22 reviews)
"We had a great stay in Portland! The place was just as described and the hosts were easy to communicate with. A good place for a couple nights within walking distance of all Portland has to offer."
United States
Lucy T.
The price is CA $111
CA $213 total
includes taxes & fees
Nov 1 - Nov 2
Studio Apartment near downtown Walkable!

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

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (86 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.
The price is CA $238
CA $722 total
includes taxes & fees
Oct 22 - Oct 23
Elegant condo - walk to Portland's best restaurants & Old Port

14. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (189 reviews)
"The property is well equipped for a long weekend. Parking was convenient. The location offered a quiet place to stay just minutes from Portland’s bustling commercial corridors. Will definitely look to book again on our next visit."
United States
William
The price is CA $333
CA $551 total
includes taxes & fees
Oct 18 - Oct 19
Glorious getaway on Portland's Eastern Promenade.

15. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.4 out of 10, Exceptional, (3 reviews)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
The price is CA $106
CA $137 total
includes taxes & fees
Oct 25 - Oct 26
Great suburban location close to town!

16. 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, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is CA $273
CA $473 total
includes taxes & fees
Nov 2 - Nov 3
Peaceful & minutes from the Old Port with private parking

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

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (72 reviews)
"Property manager was very kind but a little hard to get a hold of. Owner of the property was amazing and in contact immediately. The house is quaint, cute and perfect for a beautiful stay on the coast. We enjoyed the location more than anything. The owners left a binder with a lot of very helpful information for restaurants, stores, etc. If you want to stay in the area, you can walk almost anywhere. All in all we loved our stay and would return."
United States
James
The price is CA $305
CA $689 total
includes taxes & fees
Nov 9 - Nov 10
Arlie`s Digs! - One Block To Willard Beach!

18. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (15 reviews)
"Fantastic little spot. Great location and easy to find parking even if not using what is reserve. Home had everything necessary for a stay. Hosts were prompt with communication."
United States
Susan
The price is CA $281
CA $598 total
includes taxes & fees
Oct 20 - Oct 21
NEW 1 BDR-Heart of Munjoy Hill

19. THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking

THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
Munjoy Hill
10.0 out of 10, Exceptional, (5 reviews)
"Great place, so close to everything and a clean, quiet spot to sleep."
United States
Dan K.
The price is CA $283
CA $607 total
includes taxes & fees
Oct 19 - Oct 20
THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking

20. Charming 2-bedroom apartment with AC, WiFi in fabulous Portland

Charming 2-bedroom apartment with AC, WiFi in fabulous Portland
Munjoy Hill
8.4 out of 10, Very good, (9 reviews)
"This apartment was perfect for a stay in Portland!"
United States
Jennifer F.
The price is CA $223
CA $407 total
includes taxes & fees
Nov 4 - Nov 5
Charming 2-bedroom apartment with AC, WiFi in fabulous Portland
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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