A calm sea with a sailboat and rocky coastline.

Great Diamond Island Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Great Diamond Island vacation rentals

A yurt with a bed, a desk, and a view of the outdoors.

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
$436 nightly
The price is $475
Sep 20 - Sep 21
Total with taxes and fees
Fortland Island Campground
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

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
$279 nightly
The price is $304
Sep 17 - Sep 18
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
A street lined with buildings, one with a red door and a sign that reads "MINATO".

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
$283 nightly
The price is $308
Sep 27 - Sep 28
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

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
A modern house with a wooden exterior, a small garden, and a visible window.

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.
$430 nightly
The price is $468
Sep 8 - Sep 9
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

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
$297 nightly
The price is $324
Sep 10 - Sep 11
Total with taxes and fees
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.
$423 nightly
The price is $461
Sep 6 - Sep 7
Total with taxes and fees
Ocean View East End Studio in a Historic Victorian
A harbor with boats docked, a pier, and buildings in the background.

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.
$374 nightly
The price is $407
Sep 14 - Sep 15
Total with taxes and fees
Casco Bay Vista
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

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.
$333 nightly
The price is $363
Sep 3 - Sep 4
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A living room with a sofa, armchairs, a coffee table, and a potted plant.

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.
$174 nightly
The price is $190
Sep 3 - Sep 4
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
A modern living room with a wooden dining table, a sofa, and a coffee table.

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
$419 nightly
The price is $457
Sep 9 - Sep 10
Total with taxes and fees
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

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.
$374 nightly
The price is $408
Sep 7 - Sep 8
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
A building with a sign for "The Send Brewing Co." and a logo featuring a stylized tree.

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.
$366 nightly
The price is $399
Sep 7 - Sep 8
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
A street lined with buildings, one with a red door and a sign that reads "MINATO".

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
$378 nightly
The price is $413
Sep 3 - Sep 4
Total with taxes and fees
Glorious getaway on Portland's Eastern Promenade.
A house with a wooden staircase leading to a door marked with the number 50.

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
$309 nightly
The price is $337
Sep 30 - Oct 1
Total with taxes and fees
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
A modern living room with a wooden dining table, chairs, a TV, and a bookshelf.

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.
$346 nightly
The price is $369
Sep 7 - Sep 8
Total with taxes and fees
East end. Walk to food, beer and downtown fun.
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

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
$418 nightly
The price is $455
Sep 7 - Sep 8
Total with taxes and fees
The Weldon Hotel
A grand room with ornate chandeliers, a fireplace, and classical furniture.

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, (61 reviews)
"This spot was perfect. So cute and very well-kept. Easy to get in and navigate."
United States
Anonymous traveler
$344 nightly
The price is $375
Sep 7 - Sep 8
Total with taxes and fees
Historic Home in the West End. Private Parking.
A multi-story building with a stone facade, large windows, and a corner entrance.

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
$641 nightly
The price is $699
Sep 7 - Sep 8
Total with taxes and fees
Evalina Hotel
A beach with a wooden chair and a small building in the background.

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.
$615 nightly
The price is $671
Sep 7 - Sep 8
Total with taxes and fees
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

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

10/10 Excellent
"Nice and clean hotel with friendly staff. We went the last week of August and didn’t have a problem finding street parking at all. Valet is $40 if you don’t want to bother with looking for parking."
Duy 2-night trip
Posted 1 hour ago
Cambria Hotel Portland Downtown-Old Port

Find out more about Great Diamond Island

Everything you need to know about Great Diamond Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Great Diamond Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Great Diamond Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Great Diamond Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $166 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Great Diamond Island rentals

At Expedia, we put the best Great Diamond Island vacation 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 vacation.

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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